Advanced search
Publication Cover
Science and Technology of Advanced Materials Volume 23, 2022 - Issue 1
Submit an article Journal homepage
1,468
Views
1
CrossRef citations to date
0
Altmetric
Focus on Advancements of Functional Materials with Nanoarchitectonics as Post-Nanotechnology Concept in Materials Science

Photoinduced movement: how photoirradiation induced the movements of matter

Tetsuo Yamaguchia Department of Energy and Materials Engineering, Dongguk University-Seoul, Seoul, South KoreaORCID Iconhttps://orcid.org/0000-0002-6697-2916View further author information
ORCID Icon &
Makoto Ogawab School of Energy Science and Engineering, Vidyasirimedhi Institute of Science and Technology (VISTEC), Rayong, ThailandCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0002-3781-2016View further author information
ORCID Icon
Pages 796-844 | Received 06 Aug 2022, Accepted 27 Oct 2022, Published online: 30 Nov 2022

References

  • Bendix SW. Phototaxis. Bot Rev. 1960;26(2):145–208.
  • Jékely G. Evolution of phototaxis. Philos Trans R Soc B Biol Sci. 2009;364(1531):2795–2808.
  • Najafpour M, editor. Advances in photosynthesis - fundamental aspects. London: InTech; 2012.
  • Kohen E, Santus R, Hirschberg J. Photobiology. 1st ed. London: Academic Press; 1995.
  • Li Q, editor. Intelligent stimuli-responsive materials. Hoboken, NJ, USA: John Wiley & Sons, Inc.; 2013.
  • White TJ, editor. Photomechanical materials, composites, and systems. Chichester, UK: John Wiley & Sons, Ltd; 2017.
  • Shinkai S, Nakaji T, Ogawa T, et al. Photoresponsive crown ethers. 2. Photocontrol of ion extraction and ion transport by a bis(crown ether) with a butterfly-like motion. J Am Chem Soc. 1981;103(1):111–115. DOI:10.1021/ja00391a021
  • Bouas-Laurent H, Dürr H. Organic photochromism (IUPAC technical report). Pure Appl Chem. 2001;73(4):639–665.
  • Bullock DJW, Cumper CWN, Vogel AI. 989. Physical properties and chemical constitution. Part XLIII.* the electric dipole moments of azobenzene, azopyridine, and azoquinolines. J Chem Soc. 1965;5316–5323. DOI:10.1039/jr9650005316
  • Ye Y, Pang J, Zhou X, et al. Understanding the torsion effects on optical properties of azobenzene derivatives. Comput Theory Chem. 2016;1076:17–22.
  • Weissberger A. Dipole moment and structure of organic compounds. XVII.1 the electric moments of α- and β-stilbene dibromide and of p-diacetylbenzene. J Am Chem Soc. 1945;67(5):778–779.
  • Jakobsson FLE, Marsal P, Braun S, et al. Tuning the energy levels of photochromic diarylethene compounds for opto-electronic switch devices. J Phys Chem C. 2009;113(42):18396–18405. DOI:10.1021/jp9043573
  • Bletz M, Pfeifer-Fukumura U, Kolb U, et al. Ground-and first-excited-singlet-state electric dipole moments of some photochromic spirobenzopyrans in their spiropyran and merocyanine form. J Phys Chem A. 2002;106(10):2232–2236. DOI:10.1021/jp012562q
  • Irie M, Fukaminato T, Matsuda K, et al. Photochromism of diarylethene molecules and crystals: memories, switches, and actuators. Chem Rev. 2014;114(24):12174–12277. DOI:10.1021/cr500249p
  • Inouye M, Ueno M, Kitao T. Alkali metal recognition induced isomerization of spiropyrans. J Am Chem Soc. 1990;112(24):8977–8979.
  • Tanaka M, Ikeda T, Xu Q, et al. Synthesis and photochromism of spirobenzopyrans and spirobenzothiapyran derivatives bearing monoazathiacrown ethers and noncyclic analogues in the presence of metal ions. J Org Chem. 2002;67(7):2223–2227. DOI:10.1021/jo0162843
  • Heller CA, Fine DA, RA H. Photochromism. J Phys Chem. 1961;65(10):1908–1909.
  • Irie M. Diarylethenes for memories and switches. Chem Rev. 2000;100(5):1685–1716.
  • Kumar GS, Neckers DC. Photochemistry of azobenzene-containing polymers. Chem Rev. 1989;89(8):1915–1925.
  • Peng L, You M, Wu C, et al. Reversible Phase transfer of nanoparticles based on photoswitchable host–guest chemistry. ACS Nano. 2014;8(3):2555–2561. DOI:10.1021/nn4061385
  • Yamaguchi T, Ogawa M. Photochromic reactions in nanospace; host-guest interactions and opportunity. In: Douhal A, and Anpo M, editors. Dye photoactive mol microporous syst. 1st ed. Amsterdam: Elsevier; 2020. pp. 163–177.
  • In: Nakato T, Kawamata J, Takagi S editors. Inorganic nanosheets and nanosheet-based materials. Tokyo: Springer Japan; 2017.
  • Zhu J, Ding JJ, Liu XQ, et al. Realizing both selective adsorption and efficient regeneration using adsorbents with photo-regulated molecular gates. Chem Commun. 2016;52(21):4006–4009. DOI:10.1039/C5CC10634F
  • Cheng L, Jiang Y, Qi SC, et al. Controllable adsorption of CO2 on smart adsorbents: an interplay between amines and photoresponsive molecules. Chem Mater. 2018;30(10):3429–3437. DOI:10.1021/acs.chemmater.8b01005
  • Jiang Y, Park J, Tan P, et al. Maximizing photoresponsive efficiency by isolating metal–organic polyhedra into confined nanoscaled spaces. J Am Chem Soc. 2020;141(20):8221–8227. DOI:10.1021/jacs.9b01380
  • Baroncini M, D’Agostino S, Bergamini G, et al. Photoinduced reversible switching of porosity in molecular crystals based on star-shaped azobenzene tetramers. Nat Chem. 2015;7(8):634–640. DOI:10.1038/nchem.2304
  • Huang N, Ding X, Kim J, et al. A Photoresponsive smart covalent organic framework. Angew Chem Int Ed. 2015;54:8704–8707.
  • Getman RB, Bae YS, Wilmer CE, et al. Review and analysis of molecular simulations of methane, hydrogen, and acetylene storage in metal–organic frameworks. Chem Rev. 2012;112(2):703–723. DOI:10.1021/cr200217c
  • Bétard A, Fischer RA. Metal–organic framework thin films: from fundamentals to applications. Chem Rev. 2012;112(2):1055–1083.
  • Dolgopolova EA, Rice AM, Martin CR, et al. Photochemistry and photophysics of MOFs: steps towards MOF-based sensing enhancements. Chem Soc Rev. 2018;47(13):4710–4728. DOI:10.1039/C7CS00861A
  • Rice AM, Martin CR, Galitskiy VA, et al. Photophysics modulation in photoswitchable metal–organic frameworks. Chem Rev. 2020;120(16):8790–8813. DOI:10.1021/acs.chemrev.9b00350
  • Hosono N, Uemura T. Metal–organic frameworks as versatile media for polymer adsorption and separation. Acc Chem Res. 2021;54(18):3593–3603.
  • Le Ouay B, Watanabe C, Mochizuki S, et al. Selective sorting of polymers with different terminal groups using metal-organic frameworks. Nat Commun. 2018;9(1):3635. DOI:10.1038/s41467-018-06099-z
  • Yao QX, Ju ZF, Jin XH, et al. Novel polythreaded coordination polymer: from an armed-polyrotaxane sheet to a 3D polypseudorotaxane array, photo-thermochromic behaviors. Inorg Chem. 2009;48(4):1266–1268. DOI:10.1021/ic8021672
  • Modrow A, Zargarani D, Herges R, et al. The first porous MOF with photoswitchable linker molecules. Dalton Trans. 2011;40(16):4217–4222. DOI:10.1039/c0dt01629b
  • Jin CM, Zhu Z, Chen ZF, et al. An unusual three-dimensional water cluster in metal−organic frameworks based on ZnX2 (X = ClO4, BF4) and an azo-functional ligand. Cryst Growth Des. 2010;10(5):2054–2056. DOI:10.1021/cg100226u
  • Liu Y, Eubank JF, Cairns AJ, et al. Assembly of metal–organic frameworks (MOFs) based on indium-trimer building blocks: a porous MOF with soc topology and high hydrogen storage. Angew Chem Int Ed. 2007;46(18):3278–3283. DOI:10.1002/anie.200604306
  • Sato H, Matsuda R, Sugimoto K, et al. Photoactivation of a nanoporous crystal for on-demand guest trapping and conversion. Nat Mater. 2010;9(8):661–666. DOI:10.1038/nmat2808
  • Yanai N, Uemura T, Inoue M, et al. Guest-to-host transmission of structural changes for stimuli-responsive adsorption property. J Am Chem Soc. 2012;134(10):4501–4504. DOI:10.1021/ja2115713
  • Castellanos S, Goulet-Hanssens A, Zhao F, et al. Structural effects in visible-light-responsive metal-organic frameworks incorporating ortho-fluoroazobenzenes. Chem - A Eur J. 2016;22(2):746–752. DOI:10.1002/chem.201503503
  • Prasetya N, Donose BC, Ladewig BP. A new and highly robust light-responsive Azo-UiO-66 for highly selective and low energy post-combustion CO2 capture and its application in a mixed matrix membrane for CO2/N2 separation. J Mater Chem A. 2018;6(34):16390–16402.
  • Modrow A, Zargarani D, Herges R, et al. Introducing a photo-switchable azo-functionality inside Cr-MIL-101-NH2 by covalent post-synthetic modification. Dalton Trans. 2012;41(28):8690–8696. DOI:10.1039/c2dt30672g
  • Park J, Yuan D, Pham KT, et al. Reversible alteration of CO2 adsorption upon photochemical or thermal treatment in a metal–organic framework. J Am Chem Soc. 2012;134(1):99–102. DOI:10.1021/ja209197f
  • Jiang Y, Shi XC, Tan P, et al. Controllable CO2 capture in metal–organic frameworks: making targeted active sites respond to light. Ind Eng Chem Res. 2020;59(50):21894–21900. DOI:10.1021/acs.iecr.0c04126
  • Huang H, Sato H, Aida T. Crystalline nanochannels with pendant azobenzene groups: steric or polar effects on gas adsorption and diffusion? J Am Chem Soc. 2017;139(26):8784–8787.
  • Jiang Y, Tan P, Qi SC, et al. Metal–organic frameworks with target-specific active sites switched by photoresponsive motifs: efficient adsorbents for tailorable CO2 capture. Angew Chem Int Ed. 2019;58(20):6600–6604. DOI:10.1002/anie.201900141
  • Healey K, Liang W, Southon PD, et al. Photoresponsive spiropyran-functionalised MOF-808: postsynthetic incorporation and light dependent gas adsorption properties. J Mater Chem A. 2016;4(28):10816–10819. DOI:10.1039/C6TA04160D
  • Choi HJ, Dinca M, Long JR. Broadly hysteretic H2 adsorption in the microporous metal−organic framework Co(1,4-benzenedipyrazolate). J Am Chem Soc. 2008;130(25):7848–7850.
  • Zeleňák V, Vargová Z, Almáši M, et al. Layer-pillared zinc(II) metal–organic framework built from 4,4′-azo(bis)pyridine and 1,4-BDC. Microporous Mesoporous Mater. 2010;129(3):354–359. DOI:10.1016/j.micromeso.2009.11.002
  • Maji TK, Uemura K, Chang H-C, et al. Expanding and shrinking porous modulation based on pillared-layer coordination polymers showing selective guest adsorption. Angew Chem. 2004;116(25):3331–3334. DOI:10.1002/ange.200453923
  • Noro S, Kitagawa S, Nakamura T, et al. Synthesis and crystallographic characterization of low-dimensional and porous coordination compounds capable of supramolecular aromatic interaction using the 4,4‘-Azobis(pyridine) ligand. Inorg Chem. 2005;44(11):3960–3971. DOI:10.1021/ic048371u
  • Kondo M, Shimamura M, Noro S, et al. Microporous materials constructed from the interpenetrated coordination networks. Structures and methane adsorption properties. Chem Mater. 2000;12(5):1288–1299. DOI:10.1021/cm990612m
  • Noro S, Kondo M, Ishii T, et al. Syntheses and crystal structures of iron co-ordination polymers with 4,4′-bipyridine (4,4′-bpy) and 4,4′-azopyridine (azpy). Two-dimensional networks supported by hydrogen bonding, {[Fe(azpy)(NCS)2(MeOH)2]·azpy}n and {[Fe(4,4′-bpy)(NCS)2(H2O)2]·4,4′-bpy}n. J Chem Soc Dalt Trans. 1999;2010(10):1569–1574. DOI:10.1039/a809523j
  • Kondo M, Shimamura M, Noro S, et al. Syntheses and structures of Zn coordination polymers with 4,4′-bipyridine and 4,4′-azopyridine. Effect of counter anions on the network system. Chem Lett. 1999;28(4):285–286. DOI:10.1246/cl.1999.285
  • Kobatake S, Kitagawa D. Photomechanical behavior of photochromic diarylethene crystals. In: Koshima H, editor. Mech responsive mater soft robot. 1st ed. Weinheim, Germany: Wiley; 2020. pp. 1–28.
  • Lyndon R, Konstas K, Ladewig BP, et al. Dynamic photo-switching in metal-organic frameworks as a route to low-energy carbon dioxide capture and release. Angew Chem Int Ed. 2013;52(13):3695–3698. DOI:10.1002/anie.201206359
  • Li H, Martinez MR, Perry Z, et al. A robust metal–organic framework for dynamic light-induced swing adsorption of carbon dioxide. Chem - A Eur J. 2016;22(32):11176–11179. DOI:10.1002/chem.201602671
  • Prasetya N, Teck AA, Ladewig BP. Matrimid-JUC-62 and matrimid-PCN-250 mixed matrix membranes displaying light-responsive gas separation and beneficial ageing characteristics for CO2/N2 separation. Sci Rep. 2018;8(1):2944.
  • Jiang Y, Tan P, Qi SC, et al. Breathing metal–organic polyhedra controlled by light for carbon dioxide capture and liberation. CCS Chem. 2020;3(6):1659–1668. DOI:10.31635/ccschem.020.202000314
  • Drake HF, Xiao Z, Day GS, et al. Influence of metal identity on light-induced switchable adsorption in azobenzene-based metal–organic frameworks. ACS Appl Mater Interfaces. 2022;14(9):11192–11199. DOI:10.1021/acsami.1c18266
  • Prasetya N, Ladewig BP. Dynamic photo-switching in light-responsive JUC-62 for CO2 capture. Sci Rep. 2017;7(1):13355.
  • Zheng Y, Sato H, Wu P, et al. Flexible interlocked porous frameworks allow quantitative photoisomerization in a crystalline solid. Nat Commun. 2017;8(1):100. DOI:10.1038/s41467-017-00122-5
  • Hazra A, Bonakala S, Adalikwu SA, et al. Fluorocarbon-functionalized superhydrophobic metal–organic framework: enhanced CO2 uptake via photoinduced postsynthetic modification. Inorg Chem. 2021;60(6):3823–3833. DOI:10.1021/acs.inorgchem.0c03575
  • Xue M, Zhu G, Li Y, et al. Structure, hydrogen storage, and luminescence properties of three 3D metal−organic frameworks with NbO and PtS topologies. Cryst Growth Des. 2008;8(7):2478–2483. DOI:10.1021/cg8001114
  • Stoeck U, Krause S, Bon V, et al. A highly porous metal–organic framework, constructed from a cuboctahedral super-molecular building block, with exceptionally high methane uptake. Chem Commun. 2012;48(88):10841–10843. DOI:10.1039/c2cc34840c
  • Krause S, Evans JD, Bon V, et al. Cooperative light-induced breathing of soft porous crystals via azobenzene buckling. Nat Commun. 2022;13(1):1951. DOI:10.1038/s41467-022-29149-z
  • Krause S, Evans JD, Bon V, et al. Engineering micromechanics of soft porous crystals for negative gas adsorption. Chem Sci. 2020;11(35):9468–9479. DOI:10.1039/D0SC03727C
  • Zhai C, Lin S, Wang M, et al. Conformational freedom-enhanced optomechanical energy conversion efficiency in bulk azo-polyimides. Adv Funct Mater. 2021;31(45):2104414. DOI:10.1002/adfm.202104414
  • Hermann D, Emerich H, Lepski R, et al. Metal–organic frameworks as hosts for photochromic guest molecules. Inorg Chem. 2013;52(5):2744–2749. DOI:10.1021/ic302856b
  • Hermann D, Schwartz HA, Werker M, et al. Metal-organic frameworks as hosts for fluorinated azobenzenes: a path towards quantitative photoswitching with visible light. Chem Eur J. 2019;25(14):3606–3616. DOI:10.1002/chem.201805391
  • Garg S, Schwartz H, Kozlowska M, et al. Conductance photoswitching of metal–organic frameworks with embedded spiropyran. Angew Chem Int Ed. 2019;58(4):1193–1197. DOI:10.1002/anie.201811458
  • Tu M, Reinsch H, Rodríguez-Hermida S, et al. Reversible optical writing and data storage in an anthracene‐loaded metal‐organic framework. Angew Chem. 2018;2445–2449. DOI:10.1002/ange.201813996.
  • Myers AL, Prausnitz JM. Thermodynamics of mixed-gas adsorption. AIChE J. 1965;11(1):121–127.
  • Kim H, Yang S, Rao SR, et al. Water harvesting from air with metal-organic frameworks powered by natural sunlight. Science. 2017;356(6336):430–434. DOI:10.1126/science.aam8743
  • Al-Rowaili FN, Zahid U, Onaizi S, et al. A review for metal-organic frameworks (MOFs) utilization in capture and conversion of carbon dioxide into valuable products. J CO2 Util. 2021;53:101715.
  • Leodopoulos C, Doulia D, Gimouhopoulos K. Adsorption of cationic dyes onto bentonite. Sep Purif Rev. 2014;44(1):74–107.
  • Phuekphong AF, Imwiset KJ, Ogawa M. Designing nanoarchitecture for environmental remediation based on the clay minerals as building block. J Hazard Mater. 2020;399:122888.
  • Okada T, Seki Y, Ogawa M. Designed nanostructures of clay for controlled adsorption of organic compounds. J Nanosci Nanotechnol. 2014;14(3):2121–2134.
  • Sanchez C, Julián B, Belleville P, et al. Applications of hybrid organic–inorganic nanocomposites. J Mater Chem. 2005;15(35–36):3559–3592. DOI:10.1039/b509097k
  • Martínez-Martínez V, López Arbeloa F, editors. Dyes and photoactive molecules in microporous systems. Berlin, Heidelberg: Springer International Publishing; 2020. (Structure and Bonding; vol. 183).
  • Teepakakorn AP, Yamaguchi T, Ogawa M. The improved stability of molecular guests by the confinement into nanospaces. Chem Lett. 2019;48(5):398–409.
  • Choi G, Kim TH, Oh JM, et al. Emerging nanomaterials with advanced drug delivery functions; focused on methotrexate delivery. Coord Chem Rev. 2018;359:32–51.
  • Ogawa M, Kuroda K. Photofunctions of intercalation compounds. Chem Rev. 1995;95(2):399–438.
  • Yamaguchi T, Oh J-M, Ogawa M. Photofunctions of dye-clay hybrids: recent developments. In: Martínez-Martínez V López Arbeloa F, editors. Structure and Bonding. Berlin, Heidelberg: Springer; 2020. p. 251–320.
  • Sasai R, Ogiso H, Shindachi I, et al. Photochromism in oriented thin films prepared by the hybridization of diarylethenes in clay interlayers. Tetrahedron. 2000;56(36):6979–6984. DOI:10.1016/S0040-4020(00)00519-6
  • Shindachi I, Hanaki H, Sasai R, et al. The effect of layered sodium–magadiite on the photochromic reversibility of diarylethene immobilized on its surfaces. Chem Lett. 2004;33(9):1116–1117. DOI:10.1246/cl.2004.1116
  • Sasai R, Itoh H, Shindachi I, et al. Photochromism of clay−diarylethene hybrid materials in optically transparent gelatin films. Chem Mater. 2001;13(6):2012–2016. DOI:10.1021/cm000822v
  • Nakamura T, Takagi K, Itoh M, et al. Photodimerization of cinnamic acids controlled by molecular assemblies of surfactant amine N-oxides. J Chem Soc Perkin Trans 2. 1997;2(12):2751–2755. DOI:10.1039/a702413d
  • Shichi T, Takagi K, Sawaki Y. Stereoselectivity control of [2 + 2] photocycloaddition by changing site distances of hydrotalcite interlayers. Chem Commun. 1996;17(17):2027–2028.
  • Shichi T, Yamashita S, Takagi K. Photopolymerization of 4-vinylbenzoate and m- and p-phenylenediacrylates in hydrotalcite interlayers. Supramol Sci. 1998;5(3–4):303–308.
  • Takagi K, Shichi T, Usami H, et al. Controlled photocycloaddition of unsaturated carboxylates intercalated in hydrotalcite clay interlayers. J Am Chem Soc. 1993;115(10):4339–4344. DOI:10.1021/ja00063a060
  • Takagi K, Usami H, Fukaya H, et al. Spatially controlled photocycloaddition of a clay-intercalated stilbazolium cation. J Chem Soc Chem Commun. 1989;(16):1174–1175. DOI:10.1039/c39890001174.
  • Sasai R, Shin’ya N, Shichi T, et al. Molecular alignment and photodimerization of 4′-Chloro-4-stilbenecarboxylic acid in hydrotalcite clays: bilayer formation in the interlayers. Langmuir. 2002;15(2):413–418. DOI:10.1021/la980699a
  • Kashima I, Okubo M, Qno Y, et al. Ferromagnetism and its photo-induced effect in 2D iron mixed-valence complex coupled with photochromic spiropyran. Synth Met. 2005;155(3):703–706. DOI:10.1016/j.synthmet.2005.09.033
  • Enomoto M, Kojima N. Charge transfer phase transition and ferromagnetism in a novel iron mixed-valence complex (n-C3H7)4N[FeIIFeIII(tto)3] (tto=C2OS3). Synth Met. 2005;152(1–3):457–460.
  • Kida N, Hikita M, Kashima I, et al. Mössbauer spectroscopic study of photo-sensitive organic–inorganic hybrid system, (SP)[Fe(II)Fe(III)(dto)3](dto = C2O2S2, SP = spiropyran). Polyhedron. 2009;28(9–10):1694–1697. DOI:10.1016/j.poly.2008.10.060
  • Kida N, Hikita M, Kashima I, et al. Control of charge transfer phase transition and ferromagnetism by photoisomerization of spiropyran for an organic−inorganic hybrid system, (SP)[FeIIFeIII(dto)3] (SP= spiropyran, dto= C2O2S2. J Am Chem Soc. 2009;131(1):212–220. DOI:10.1021/ja806879a
  • Tanaka N, Okazawa A, Sugahara A, et al. Development of a photoresponsive organic–inorganic hybrid magnet: layered cobalt hydroxides intercalated with spiropyran anions. Bull Chem Soc Jpn. 2015;88(8):1150–1155. DOI:10.1246/bcsj.20150129
  • Abellán G, Coronado E, Martí-Gastaldo C, et al. Photo-switching in a hybrid material made of magnetic layered double hydroxides intercalated with azobenzene molecules. Adv Mater. 2014;26(24):4156–4162. DOI:10.1002/adma.201400713
  • Abellán G, Jordá JL, Atienzar P, et al. Stimuli-responsive hybrid materials: breathing in magnetic layered double hydroxides induced by a thermoresponsive molecule. Chem Sci. 2015;6(3):1949–1958. DOI:10.1039/C4SC03460K
  • Okubo M, Enomoto M, Kojima N. Study on photomagnetism of 2-D magnetic compounds coupled with photochromic diarylethene cations. Synth Met. 2005;152(1–3):461–464.
  • Ogawa M, Fujii K, Kuroda K, et al. Preparation of montmorillonite-p-aminoazobenzene intercalation compounds and their photochemical behavior. Mater Res Soc Symp Proc. 1991;233:89–94.
  • Okada T, Nozaki N, Seo J, et al. Photoinduced structural changes of cationic azo dyes confined in a two dimensional nanospace by two different mechanisms. RSC Adv. 2017;7(13):8077–8081. DOI:10.1039/C6RA27749G
  • Okada T, Sakai H, Ogawa M. The effect of the molecular structure of a cationic azo dye on the photoinduced intercalation of phenol in a montmorillonite. Appl Clay Sci. 2008;40(1–4):187–192.
  • Ogawa M. Photoisomerization of azobenzene in the interlayer space of magadiite. J Mater Chem. 2002;12(11):3304–3307.
  • Ogawa M, Ishikawa A. Controlled microstructures of amphiphilic cationic azobenzene-montmorillonite intercalation compounds. J Mater Chem. 1998;8(2):463–467.
  • Ogawa M, Ishii T, Miyamoto N, et al. Intercalation of a cationic azobenzene into montmorillonite. Appl Clay Sci. 2003;22(4):179–185. DOI:10.1016/S0169-1317(02)00157-6
  • Kim CS, Yates DM, Heaney PJ. The layered sodium silicate magadiite: an analog to smectite for benzene sorption from water. Clays Clay Miner. 1997;45(6):881–885.
  • Ogawa M, Ishii T, Miyamoto N, et al. Photocontrol of the basal spacing of azobenzene–magadiite intercalation compound. Adv Mater. 2001;13(14):1107–1109. DOI:10.1002/1521-4095(200107)13:14<1107:AID-ADMA1107>3.0.CO;2-O
  • Heinz H, Vaia RA, Koerner H, et al. Photoisomerization of azobenzene grafted to layered silicates: simulation and experimental challenges. Chem Mater. 2008;20(20):6444–6456. DOI:10.1021/cm801287d
  • Fujita T, Iyi N, Klapyta Z. Optimum conditions for photoresponse of azobenzene-organophilic tetrasilicic mica complexes. Mater Res Bull. 2001;36(3–4):557–571.
  • Fujita T, Iyi N, Klapyta Z, et al. Photomechanical response of azobenzene/organophilic mica complexes. Mater Res Bull. 2003;38(15):2009–2017. DOI:10.1016/j.materresbull.2003.09.012
  • Ogawa M, Iwata D. Arrangements of interlayer quaternary ammonium ions in a layered silicate, octosilicate. Cryst Growth Des. 2010;10(5):2068–2072.
  • Lagaly G, Fernandez Gonzalez M, Weiss A. Problems in layer-charge determination of montmorillonites. Clay Miner. 1976;11(3):173–187.
  • Koteja A, Szczerba M, Matusik J. Smectites intercalated with azobenzene and aminoazobenzene: structure changes at nanoscale induced by UV light. J Phys Chem Solids. 2017;111:294–303.
  • Abbaszad Rafi A, Hamidi N, Bashir-Hashemi A, et al. Photo-switchable nanomechanical systems comprising a nanocontainer (montmorillonite) and light-driven molecular jack (azobenzene-imidazolium ionic liquids) as drug delivery systems; synthesis, characterization, and in vitro release studies. ACS Biomater Sci Eng. 2018;4(1):184–192. DOI:10.1021/acsbiomaterials.7b00621
  • Okada T, Watanabea Y, Ogawa M. Photocontrol of the adsorption behavior of phenol for an azobenzene-montmorillonite intercalation compound. Chem Commun. 2004;1(3):320–321.
  • Okada T, Watanabe Y, Ogawa M. Photoregulation of the intercalation behavior of phenol for azobenzene–clay intercalation compounds. J Mater Chem. 2005;15(9):987.
  • Nabetani Y, Takamura H, Hayasaka Y, et al. An artificial muscle model unit based on inorganic nanosheet sliding by photochemical reaction. Nanoscale. 2013;5(8):3182–3193. DOI:10.1039/c3nr34308a
  • Nabetani Y, Takamura H, Hayasaka Y, et al. A photoactivated artificial muscle model unit: reversible, photoinduced sliding of nanosheets. J Am Chem Soc. 2011;133(43):17130–17133. DOI:10.1021/ja207278t
  • Nabetani Y, Takamura H, Uchikoshi A, et al. Photo-induced morphological winding and unwinding motion of nanoscrolls composed of niobate nanosheets with a polyfluoroalkyl azobenzene derivative. Nanoscale. 2016;8(24):12289–12293. DOI:10.1039/C6NR02177H
  • Tong Z, Takagi S, Shimada T, et al. Photoresponsive multilayer spiral nanotubes: intercalation of polyfluorinated cationic azobenzene surfactant into potassium niobate. J Am Chem Soc. 2006;128(3):684–685. DOI:10.1021/ja0564564
  • Guo S, Matsukawa K, Miyata T, et al. Photoinduced bending of self-assembled azobenzene–siloxane hybrid. J Am Chem Soc. 2015;137(49):15434–15440. DOI:10.1021/jacs.5b06172
  • Helmy S, Leibfarth FA, Oh S, et al. Photoswitching using visible light : a new class of organic photochromic molecules. J Am Chem Soc. 2014;136(23):8169–8172. DOI:10.1021/ja503016b
  • Gomes RFA, Coelho JAS, Afonso CAM. Synthesis and applications of Stenhouse salts and derivatives. Chem - A Eur J. 2018;24(37):9170–9186.
  • Lerch MM, Szymański W, Feringa BL. The (photo)chemistry of stenhouse photoswitches: guiding principles and system design. Chem Soc Rev. 2018;47(6):1910–1937.
  • García-López V, Chen F, Nilewski LG, et al. Molecular machines open cell membranes. Nature. 2017;548(7669):567–572. DOI:10.1038/nature23657
  • Shinkai S, Minami T, Kusano Y, et al. Photoresponsive crown ethers 5. Light-driven ion transport by crown ethers with a photoresponsive anionic cap. J Am Chem Soc. 1982;104(7):1967–1972. DOI:10.1021/ja00371a028
  • Shinkai S, Shigematsu K, Sato M, et al. Photoresponsive crown ethers. Part 6. Ion transport mediated by photoinduced cis—trans interconversion of azobis(benzocrown ethers). J Chem Soc Perkin Trans 1. 1982;2735–2739. DOI:10.1039/P19820002735.
  • Shinkai S, Ishihara M, Ueda K, et al. Photoresponsive crown ethers Part 14. Photoregulated crown–metal complexation by competitive intramolecular tail(ammonium)-biting. J Chem Soc Perkin Trans 2. 1985;7(4):511–518. DOI:10.1039/P29850000511
  • Sakamoto H, Takagaki H, Nakamura M, et al. Photoresponsive liquid membrane transport of alkali metal ions using crowned spirobenzopyrans. Anal Chem. 2005;77(7):1999–2006. DOI:10.1021/ac048642i
  • Khairutdinov RF, Hurst JK. Light-driven transmembrane ion transport by spiropyran−crown ether supramolecular assemblies. Langmuir. 2004;20(5):1781–1785.
  • Xie X, Crespo GA, Mistlberger G, et al. Photocurrent generation based on a light-driven proton pump in an artificial liquid membrane. Nat Chem. 2014;6(3):202–207. DOI:10.1038/nchem.1858
  • Steinberg-Yfrach G, Liddell PA, Hung S-C, et al. Conversion of light energy to proton potential in liposomes by artificial photosynthetic reaction centres. Nature. 1997;385:239–241.
  • Steinberg-Yfrach G, Rigaud JL, Durantini EN, et al. Light-driven production of ATP catalysed by F0F1-ATP synthase in an artificial photosynthetic membrane. Nature. 1998;392(6675):479–482. DOI:10.1038/33116
  • de Thieulloy L, Barois C, Mongin C, et al. Is it possible to”simply” predict the photoejection of a cation? Example of azacrown-substituted [(bpy)Re(CO)3L]+ complexes. J Photochem Photobiol A Chem. 2022;426:113714.
  • Bennett IM, Vanegas Farfano HM, Bogani F, et al. Active transport of Ca2+ by an artificial photosynthetic membrane. Nature. 2002;420:398–401.
  • Lewis JD, Perutz RN, Moore JN. Light-controlled ion switching: direct observation of the complete nanosecond release and microsecond recapture cycle of an azacrown-substituted [(bpy)Re(CO)3L]+ complex. J Phys Chem A. 2004;108(42):9037–9047.
  • Salunke SB, Malla JA, Talukdar P. Phototriggered release of a transmembrane chloride carrier from an o-nitrobenzyl-linked procarrier. Angew Chem Int Ed. 2019;58(16):5354–5358.
  • Shinkai S, Honda Y, Ueda K, et al. Photoresponsive crown ethers. 12. Photocontrol of metal ion complexation with thiacrown ethers. Bull Chem Soc Jpn. 1984;57(8):2144–2149. DOI:10.1246/bcsj.57.2144
  • Shinkai S, Shigematsu K, Honda Y, et al. Photoresponsive crown ethers 13. Synthesis of photoresponsive NS2O crown ethers and application of the Cu(I) complexes to O2-Binding. Bull Chem Soc Jpn. 1984;57:2879–2884.
  • Shinkai S, Miyazaki K, Manabe O. Photoresponsive crown ethers. Part 18. Photochemically “switched-on” crown ethers containing an intra-annular azo substituent and their application to membrane transport. J Chem Soc Perkin Trans 1. 1987;449–456. DOI:10.1039/P19870000449
  • Shinkai S, Ogawa T, Nakaji T, et al. Photocontrolled extraction ability of azobenzene-bridged azacrown ether. Tetrahedron Lett. 1979;20(47):4569–4572. DOI:10.1016/S0040-4039(01)86651-X
  • Shinkai S, Nakaji T, Nishida Y, et al. Photoresponsive crown ethers. 1. Cis-trans isomerism of azobenzene as a tool to enforce conformational changes of crown ethers and polymers. J Am Chem Soc. 1980;102(18):5860–5865. DOI:10.1021/ja00538a026
  • Shinkai S, Shigematsu K, Kusano Y, et al. Photoresponsive crown ethers. Part 3. Photocontrol of ion extraction and ion transport by several photofunctional bis(crown ethers). J Chem Soc Perkin Trans 1. 1981;3279–3283. DOI:10.1039/p19810003279.
  • Shinkai S, Ogawa T, Kusano Y, et al. Photoresponsive crown ethers. 4. influence of alkali metal cations on photoisomerization and thermal isomerization of azobis(benzocrown ether)s. J Am Chem Soc. 1982;104(7):1960–1967. DOI:10.1021/ja00371a027
  • Shinkai S, Minami T, Kusano Y, et al. Photoresponsive crown ethers. 8. Azobenzenophane-type “switched-on” crown ethers which exhibit an all-or-nothing change in ion-binding ability. J Am Chem Soc. 1983;105(7):1851–1856. DOI:10.1021/ja00345a029
  • Shinkai S, Honda Y, Minami T, et al. Photoresponsive crown ethers. 9. Cylindrical and phane crown ethers with azobenzene segments as a light-switch functional group. Bull Chem Soc Jpn. 1983;56(6):1700–1704. DOI:10.1246/bcsj.56.1700
  • Shinkai S, Honda Y, Ueda K, et al. Photoresponsive crown ethers. Part 11. Azobenzene‐pillared cylindrical macrocycle as a photoresponsive receptor. ISR J Chem. 1984;24(4):302–306. DOI:10.1002/ijch.198400052
  • Choi YR, Kim GC, Jeon HG, et al. Azobenzene-based chloride transporters with light-controllable activities. Chem Commun. 2014;50(97):15305–15308. DOI:10.1039/C4CC07560A
  • Kerckhoffs A, Langton MJ. Reversible photo-control over transmembrane anion transport using visible-light responsive supramolecular carriers. Chem Sci. 2020;11(24):6325–6331.
  • Ahmad M, Metya S, Das A, et al. A sandwich azobenzene–diamide dimer for photoregulated chloride transport. Chem Eur J. 2020;26(40):8703–8708. DOI:10.1002/chem.202000400
  • Li H, Zhang Y, Jia Z, et al. Theoretical design on molecular tweezers of sodium cyanide by zinc porphyrin-azo-crown ether triads receptor. J Phys Org Chem. 2019;32(8):1–10. DOI:10.1002/poc.3963
  • Shinkai S, Kinda H, Ishihara M, et al. Photoresponsive crown ethers. 10. Metal complexation by light-switched crown ethers immobilized in polymer matrices. J Polym Sci Part A. 1983;21(12):3525–3539. DOI:10.1002/pol.1983.170211214
  • Sakamoto H, Yokohata T, Yamamura T, et al. Liquid−liquid extraction of alkali metal ions with photochromic crowned spirobenzopyrans. Anal Chem. 2002;74(11):2522–2528. DOI:10.1021/ac020003p
  • Li E, Kang J, Ye P, et al. A prospective material for the highly selective extraction of lithium ions based on a photochromic crowned spirobenzopyran. J Mater Chem B. 2019;7(6):903–907. DOI:10.1039/C8TB02906G
  • Kimura K, Nakahara Y. Analytical and separation chemistry by taking advantage of organic photochromism combined with macrocyclic chemistry. Anal Sci. 2009;25(1):9–20.
  • Nakamura M, Sakamoto H, Kimura K. Photocontrollable cation extraction with crowned oligo(spirobenzopyran)s. Anal Sci. 2005;21(4):403–408.
  • Kimura K, Sakamoto H, Nakamura M. Molecular design and applications of photochromic crown compounds —how can we manipulate metal ions photochemically?. Bull Chem Soc Jpn. 2003;76(2):225–245.
  • Kandori H, Inoue K, Tsunoda SP. Light-driven sodium-pumping rhodopsin: a new concept of active transport. Chem Rev. 2018;118(21):10646–10658.
  • Engelhard C, Chizhov I, Siebert F, et al. Microbial halorhodopsins: light-driven chloride pumps. Chem Rev. 2018;118(21):10629–10645. DOI:10.1021/acs.chemrev.7b00715
  • Xie G, Li P, Zhao Z, et al. Bacteriorhodopsin-inspired light-driven artificial molecule motors for transmembrane mass transportation. Angew Chem Int Ed. 2018;57(51):16708–16712. DOI:10.1002/anie.201809627
  • Xiao K, Giusto P, Chen F, et al. Light-driven directional ion transport for enhanced osmotic energy harvesting. Natl Sci Rev. 2021;8(8):nwaa231. DOI:10.1093/nsr/nwaa231
  • Koçer A, Walko M, Meijberg W, et al. A light-actuated nanovalve derived from a channel protein. Science. 2005;309(5735):755–758. DOI:10.1126/science.1114760
  • Bonardi F, London G, Nouwen N, et al. Light-induced control of protein translocation by the SecYEG complex. Angew Chem Int Ed. 2010;49(40):7234–7238. DOI:10.1002/anie.201002243
  • Muramatsu S, Kinbara K, Taguchi H, et al. Semibiological molecular machine with an implemented “AND” logic gate for regulation of protein folding. J Am Chem Soc. 2006;128(11):3764–3769. DOI:10.1021/ja057604t
  • Sendai T, Biswas S, Aida T. Photoreconfigurable supramolecular nanotube. J Am Chem Soc. 2013;135(31):11509–11512.
  • Yang X, Ma G, Zheng S, et al. Optical control of CRAC channels using photoswitchable azopyrazoles. J Am Chem Soc. 2020;142(20):9460–9470. DOI:10.1021/jacs.0c02949
  • Sukharev S, Anishkin A. Mechanosensitive channels: what can we learn from “simple” model systems? Trends Neurosci. 2004;27(6):345–351.
  • du Plessis DJF, Berrelkamp G, Nouwen N, et al. The lateral gate of SecYEG opens during protein translocation. J Biol Chem. 2009;284(23):15805–15814. DOI:10.1074/jbc.M901855200
  • Bukau B, Horwich AL. The Hsp70 and Hsp60 chaperone machines. Cell. 1998;92:351–366.
  • Berridge MJ, Bootman MD, Roderick HL. Calcium signalling: dynamics, homeostasis and remodelling. Nat Rev Mol Cell Biol. 2003;4(7):517–529.
  • Derler I, Schindl R, Fritsch R, et al. The action of selective CRAC channel blockers is affected by the Orai pore geometry. Cell Calcium. 2013;53(2):139–151. DOI:10.1016/j.ceca.2012.11.005
  • Fyles TM, James TD, Kaye KC. Activities and modes of action of artificial ion-channel mimics. J Am Chem Soc. 1993;115(26):12315–12321.
  • Voyer N, Robitaille M. A novel functional artificial ion channel. J Am Chem Soc. 1995;117(24):6599–6600.
  • Hu Y, Roberts JM, Kilgore HR, et al. Triple, mutually orthogonal bioorthogonal pairs through the design of electronically activated sulfamate-containing cycloalkynes. J Am Chem Soc. 2020;142(44):18859–18865. DOI:10.1021/jacs.0c06725
  • Liu T, Bao C, Wang H, et al. Self-assembly of crown ether-based amphiphiles for constructing synthetic ion channels: the relationship between structure and transport activity. New J Chem. 2014;38(8):3507–3513. DOI:10.1039/C4NJ00297K
  • Bhosale S, Sisson AL, Talukdar P, et al. Photoproduction of proton gradients with π-stacked fluorophore scaffolds in lipid bilayers. Science. 2006;313(5783):84–86. DOI:10.1126/science.1126524
  • Bao C, Ma M, Meng F, et al. Efficient synthetic supramolecular channels and their light-deactivated ion transport in bilayer lipid membranes. New J Chem. 2015;39(8):6297–6302. DOI:10.1039/C5NJ00937E
  • Zhou Y, Chen Y, Zhu P, et al. Reversible photo-gated transmembrane channel assembled from an acylhydrazone-containing crown ether triad. Chem Commun. 2017;53(26):3681–3684. DOI:10.1039/C7CC01123G
  • Liu T, Bao C, Wang H, et al. Light-controlled ion channels formed by amphiphilic small molecules regulate ion conduction via cis–trans photoisomerization. Chem Commun. 2013;49(87):10311–10313. DOI:10.1039/c3cc45618h
  • Wang WZ, Huang LB, Zheng SP, et al. Light-driven molecular motors boost the selective transport of alkali metal ions through phospholipid bilayers. J Am Chem Soc. 2021;143(38):15653–15660. DOI:10.1021/jacs.1c05750
  • Matile S, Sakai N. The characterization of synthetic ion channels and pores. In: Schalley C, editor. Analytical Methods in Supramolecular Chemistry. Weinheim, Germany: Wiley-VCH; 2007. pp. 391–418.
  • Vlassiouk I, Park C-D, Vail SA, et al. Control of nanopore wetting by a photochromic spiropyran: a light-controlled valve and electrical switch. Nano Lett. 2006;6(5):1013–1017. DOI:10.1021/nl060313d
  • Wang G, Bohaty AK, Zharov I, et al. Photon gated transport at the glass nanopore electrode. J Am Chem Soc. 2006;128(41):13553–13558. DOI:10.1021/ja064274j
  • Bohaty AK, Newton MR, Zharov I. Light-controlled ion transport through spiropyran-modified nanoporous silica colloidal films. J Porous Mater. 2010;17(4):465–473.
  • Zhang M, Hou X, Wang J, et al. Light and pH cooperative nanofluidic diode using a spiropyran-functionalized single nanochannel. Adv Mater. 2012;24(18):2424–2428. DOI:10.1002/adma.201104536
  • Takashima Y, Harada A. Functioning via host–guest interactions. J Incl Phenom Macrocyclic Chem. 2017;87(3–4):313–330.
  • Harada A, Kobayashi R, Takashima Y, et al. Macroscopic self-assembly through molecular recognition. Nat Chem. 2011;3(1):34–37. DOI:10.1038/nchem.893
  • Liu P, Zhou T, Teng Y, et al. Light-induced heat driving active ion transport based on 2D MXene nanofluids for enhancing osmotic energy conversion. CCS Chem. 2021;3(4):1325–1335. DOI:10.31635/ccschem.020.202000296
  • Lin F, Lonergan MC. Semiconducting bipolar membranes: photochemical salt pumps. ACS Appl Energy Mater. 2020;3(5):4103–4107.
  • Barrio J, Sánchez-Somolinos C. Light to shape the future : from photolithography to 4D printing. Adv Opt Mater. 2019;7(16):1900598.
  • Phillips HM, Callahan DL, Sauerbrey R, et al. Sub-100 nm lines produced by direct laser ablation in polyimide. Appl Phys Lett. 1991;58(24):2761–2763. DOI:10.1063/1.104778
  • Natansohn A, Rochon P. Photoinduced motions in azo-containing polymers. Chem Rev. 2002;102(11):4139–4175.
  • Viswanathan NK, Kim DY, Bian S, et al. Surface relief structures on azo polymer films. J Mater Chem. 1999;9(9):1941–1955. DOI:10.1039/a902424g
  • Oscurato SL, Salvatore M, Maddalena P, et al. From nanoscopic to macroscopic photo-driven motion in azobenzene-containing materials. Nanophotonics. 2018;7(8):1387–1422. DOI:10.1515/nanoph-2018-0040
  • Lee S, Kang HS, Park JK. Directional photofluidization lithography: micro/nanostructural evolution by photofluidic motions of azobenzene materials. Adv Mater. 2012;24(16):2069–2103.
  • Kim CB, Janes DW, Zhou SX, et al. Bidirectional control of flow in thin polymer films by photochemically manipulating surface tension. Chem Mater. 2015;27(13):4538–4545. DOI:10.1021/acs.chemmater.5b01744
  • Jones AR, Kim CB, Zhou SX, et al. Generating large thermally stable marangoni-driven topography in polymer films by stabilizing the surface energy gradient. Macromolecules. 2017;50(11):4588–4596. DOI:10.1021/acs.macromol.7b00055
  • Dai M, Picot OT, Hughes-Brittain NF, et al. Formation of relief structures on fibres by photo-embossing. J Mater Chem. 2011;21(39):15527–15531. DOI:10.1039/c1jm12365c
  • Liedtke A, Lei C, O’Neill M, et al. One-step photoembossing for submicrometer surface relief structures in liquid crystal semiconductors. ACS Nano. 2010;4(6):3248–3253. DOI:10.1021/nn100012g
  • Ubukata T, Nakayama M, Sonoda T, et al. Highly sensitive formation of stable surface relief structures in bisanthracene films with spatially patterned photopolymerization. ACS Appl Mater Interfaces. 2016;8(34):21974–21978. DOI:10.1021/acsami.6b07943
  • Kawatsuki N, Tashima A, Manabe S, et al. Holographic recording in a photo-cross-linkable liquid crystalline copolymer using a 325-nm laser with various polarizations. React Funct Polym. 2010;70(12):980–985. DOI:10.1016/j.reactfunctpolym.2010.10.006
  • Lavielle L, Croutxé-Barghorn C, Schuller E, et al. Photopolymerization of acrylate films under an imposed spatial irradiation: thermodynamics of relief self-development. J Colloid Interface Sci. 1997;192(1):149–155. DOI:10.1006/jcis.1997.4972
  • Kawatsuki N, Hasegawa T, Ono H, et al. Formation of polarization gratings and surface relief gratings in photocrosslinkable polymer liquid crystals by polarization holography. Adv Mater. 2003;15(12):991–994. DOI:10.1002/adma.200304988
  • Veltri A, Caputo R, Umeton C, et al. Model for the photoinduced formation of diffraction gratings in liquid-crystalline composite materials. Appl Phys Lett. 2004;84(18):3492–3494. DOI:10.1063/1.1738182
  • Goldenberg L, Sakhno O, Stumpe J. Application of Norland adhesive for holographic recording. Opt Mater. 2005;27(8):1379–1385.
  • Aoki K, Ichimura K. Self-developable surface relief photoimaging generated by anionic UV-curing of epoxy resins. Polym J. 2009;41(11):988–992.
  • Hughes-Brittain NF, Qiu L, Wang W, et al. Photoembossing of surface relief structures in polymer films for biomedical applications. J Biomed Mater Res - Part B Appl Biomater. 2014;102(2):214–220. DOI:10.1002/jbm.b.32997
  • Picot OT, Alcalá R, Sánchez C, et al. Manufacturing of surface relief structures in moving substrates using photoembossing and pulsed-interference holography. Macromol Mater Eng. 2013;298(1):33–37. DOI:10.1002/mame.201100433
  • Hashimoto S, Aizawa M, Akamatsu N, et al. Simultaneous formation behaviour of surface structures and molecular alignment by patterned photopolymerisation. Liq Cryst. 2019;46(13–14):1995–2002. DOI:10.1080/02678292.2019.1610980
  • Ubukata T, Yamamoto S, Moriya Y, et al. Photo-triggered surface relief of polystyrene films-highly photo-sensitive formation by the addition of a benzophenone derivative. J Photopolym Sci Technol. 2012;25(5):675–678. DOI:10.2494/photopolymer.25.675
  • Fiorini C, Prudhomme N, De Veyrac G, et al. Molecular migration mechanism for laser induced surface relief grating formation. Synth Met. 2000;115(1–3):121–125. DOI:10.1016/S0379-6779(00)00332-5
  • Yager KG, Barrett CJ. All-optical patterning of azo polymer films. Curr Opin Solid State Mater Sci. 2001;5(6):487–494.
  • Baldus O, Zilker SJ. Surface relief gratings in photoaddressable polymers generated by cw holography. Appl Phys B Lasers Opt. 2001;72(4):425–427.
  • Hubert C, Fiorini-Debuisschert C, Maurin I, et al. Spontaneous patterning of hexagonal structures in an azo-polymer using light-controlled mass transport. Adv Mater. 2002;14(10):729–732. DOI:10.1002/1521-4095(20020517)14:10<729:AID-ADMA729>3.0.CO;2-1
  • Sumaru K, Fukuda T, Kimura T, et al. Photoinduced surface relief formation on azopolymer films: a driving force and formed relief profile. J Appl Phys. 2002;91(5):3421–3430. DOI:10.1063/1.1432482
  • Ciuchi F, Mazzulla A, Carbone G, et al. Complex structures of surface relief induced by holographic recording in azo-dye-doped elastomer thin films. Macromolecules. 2003;36(15):5689–5693. DOI:10.1021/ma021772d
  • Ivanov M, Rochon P. Infrared-laser-induced periodic surface structure in azo-dye polymer. Appl Phys Lett. 2004;84(22):4511–4513.
  • Yu H, Okano K, Shishido A, et al. Enhancement of surface-relief gratings recorded on amphiphilic liquid-crystalline diblock copolymer by nanoscale phase separation. Adv Mater. 2005;17(18):2184–2188. DOI:10.1002/adma.200500346
  • Oliveira ON, Dos Santos DS, Balogh DT, et al. Optical storage and surface-relief gratings in azobenzene-containing nanostructured films. Adv Colloid Interface Sci. 2005;116(1–3):179–192. DOI:10.1016/j.cis.2005.05.008
  • Ubukata T, Isoshima T, Hara M. Wavelength-programmable organic distributed-feedback laser based on a photoassisted polymer-migration system. Adv Mater. 2005;17(13):1630–1633.
  • Kim DY, Tripathy SK, Li L, et al. Laser-induced holographic surface relief gratings on nonlinear optical polymer films. Appl Phys Lett. 1995;66(10):1166. DOI:10.1063/1.113845
  • You F, Paik MY, Häckel M, et al. Control and suppression of surface relief gratings in liquid-crystalline perfluoroalkyl–azobenzene polymers. Adv Funct Mater. 2006;16(12):1577–1581. DOI:10.1002/adfm.200500711
  • Ubukata T, Isoshima T, Hara M. Wavelength programmable organic distributed feedback laser using a photoinduced surface relief grating. Mol Cryst Liq Cryst. 2006;445(1):[269/[559]–273/[563].
  • He Y, Yin J, Che P, et al. Epoxy-based polymers containing methyl-substituted azobenzene chromophores and photoinduced surface relief gratings. Eur Polym J. 2006;42(2):292–301. DOI:10.1016/j.eurpolymj.2005.07.019
  • Yager KG, Barrett CJ. Photomechanical surface patterning in azo-polymer materials. Macromolecules. 2006;39(26):9320–9326.
  • Kulikovska O, Goldenberg LM, Kulikovsky L, et al. Smart ionic sol−gel-based azobenzene materials for optical generation of microstructures. Chem Mater. 2008;20(10):3528–3534. DOI:10.1021/cm800106x
  • Gao J, He Y, Liu F, et al. Azobenzene-containing supramolecular side-chain polymer films for laser-induced surface relief gratings. Chem Mater. 2007;19(16):3877–3881. DOI:10.1021/cm0707197
  • Yu H, Naka Y, Shishido A, et al. Well-defined liquid-crystalline diblock copolymers with an azobenzene moiety: synthesis, photoinduced alignment and their holographic properties. Macromolecules. 2008;41(21):7959–7966. DOI:10.1021/ma801077g
  • Lee S, Jeong YC, Park JK. Unusual surface reliefs from photoinduced creeping and aggregation behavior of azopolymer. Appl Phys Lett. 2008;93(3):031912.
  • Guo M, Xu Z, Wang X. Photofabrication of two-dimensional quasi-crystal patterns on UV-curable molecular azo glass films. Langmuir. 2008;24(6):2740–2745.
  • He Y, Gu X, Guo M, et al. Dendritic azo compounds as a new type amorphous molecular material with quick photoinduced surface-relief-grating formation ability. Opt Mater. 2008;31(1):18–27. DOI:10.1016/j.optmat.2008.01.003
  • Rochon P, Batalla E, Natansohn A. Optically induced surface gratings on azoaromatic polymer films. Appl Phys Lett. 1995;136(2):136.
  • Lev B, Chernyshuk SB, Yamamoto T, et al. Photochemical switching between colloidal photonic crystals at the nematic-air interface. Phys Rev E. 2008;78(2):020701. DOI:10.1103/PhysRevE.78.020701
  • Zhang Y, Zhang W, Chen X, et al. Synthesis of novel three-arm star azo side-chain liquid crystalline polymer via ATRP and photoinduced surface relief gratings. J Polym Sci Part A. 2008;46(3):777–789. DOI:10.1002/pola.22423
  • Zhang Q, Wang X, Barrett CJ, et al. Spacer-free ionic dye−polyelectrolyte complexes: influence of molecular structure on liquid crystal order and photoinduced motion. Chem Mater. 2009;21(14):3216–3227. DOI:10.1021/cm900810r
  • Goldenberg LM, Kulikovsky L, Kulikovska O, et al. New materials with detachable azobenzene: effective, colourless and extremely stable surface relief gratings. J Mater Chem. 2009;19(43):8068–8071. DOI:10.1039/b918130j
  • Vapaavuori J, Priimagi A, Kaivola M. Photoinduced surface-relief gratings in films of supramolecular polymer–bisazobenzene complexes. J Mater Chem. 2010;20(25):5260–5264.
  • Yin J, Ye G, Wang X. Self-structured surface patterns on molecular azo glass films induced by laser light irradiation. Langmuir. 2010;26(9):6755–6761.
  • Ambrosio A, Maddalena P, Carella A, et al. Two-photon induced self-structuring of polymeric films based on Y-shape azobenzene chromophore. J Phys Chem C. 2011;115(28):13566–13570. DOI:10.1021/jp200050h
  • Schuh C, Lomadze N, Rühe J, et al. Photomechanical degrafting of azo-functionalized poly(methacrylic acid) (PMAA) brushes. J Phys Chem B. 2011;115(35):10431–10438. DOI:10.1021/jp2041229
  • Lomadze N, Kopyshev A, Rühe J, et al. Light-induced chain scission in photosensitive polymer brushes. Macromolecules. 2011;44(18):7372–7377. DOI:10.1021/ma201016q
  • Wang X, Yin J, Wang X. Photoinduced self-structured surface pattern on a molecular azo glass film: structure–property relationship and wavelength correlation. Langmuir. 2011;27(20):12666–12676.
  • Barrett CJ, Natansohn AL, Rochon PL. Mechanism of optically inscribed high-efficiency diffraction gratings in azo polymer films. J Phys Chem. 1996;100(21):8836–8842.
  • Wang X, Yin J, Wang X. Self-structured surface patterns on epoxy-based azo polymer films induced by laser light irradiation. Macromolecules. 2011;44(17):6856–6867.
  • Ahmed R, Priimagi A, Faul CFJ, et al. Redox-active, organometallic surface-relief gratings from azobenzene-containing polyferrocenylsilane block copolymers. Adv Mater. 2012;24(7):926–931. DOI:10.1002/adma.201103793
  • Ambrosio A, Marrucci L, Borbone F, et al. Light-induced spiral mass transport in azo-polymer films under vortex-beam illumination. Nat Commun. 2012;3(1):989. DOI:10.1038/ncomms1996
  • Jacquart A, Morin E, Yang F, et al. Influence of extrinsic and intrinsic parameters onto the formation of surface relief gratings in polar azo molecular glasses. Dyes Pigm. 2012;92:790–797.
  • Priimagi A, Cavallo G, Forni A, et al. Halogen bonding versus hydrogen bonding in driving self-assembly and performance of light-responsive supramolecular polymers. Adv Funct Mater. 2012;22(12):2572–2579. DOI:10.1002/adfm.201200135
  • Priimagi A, Saccone M, Cavallo G, et al. Photoalignment and surface-relief-grating formation are efficiently combined in low-molecular-weight halogen-bonded complexes. Adv Mater. 2012;24(44):345–352. DOI:10.1002/adma.201204060
  • Koskela JE, Vapaavuori J, Hautala J, et al. Surface-relief gratings and stable birefringence inscribed using light of broad spectral range in supramolecular polymer-bisazobenzene complexes. J Phys Chem C. 2012;116(3):2363–2370. DOI:10.1021/jp210706n
  • Schab-Balcerzak E, Sobolewska A, Stumpe J, et al. Surface relief gratings in azobenzene supramolecular systems based on polyimides. Opt Mater. 2012;35(2):155–167. DOI:10.1016/j.optmat.2012.07.029
  • Ishikawa D, Ito E, Han M, et al. Effect of the steric molecular structure of azobenzene on the formation of self-assembled monolayers with a photoswitchable surface morphology. Langmuir. 2013;29(14):4622–4631. DOI:10.1021/la302552v
  • Ambrosio A, Maddalena P, Marrucci L. Molecular model for light-driven spiral mass transport in azopolymer films. Phys Rev Lett. 2013;110(14):1–5.
  • Darracq B, Chaput F, Lahlil K, et al. Photoinscription of surface relief gratings on azo-hybrid gels. Adv Mater. 1998;10(14):1133–1136. DOI:10.1002/(SICI)1521-4095(199810)10:14<1133:AID-ADMA1133>3.0.CO;2-F
  • Vapaavuori J, Priimagi A, Soininen AJ, et al. Photoinduced surface patterning of azobenzene-containing supramolecular dendrons, dendrimers and dendronized polymers. Opt Mater Express. 2013;3(6):711. DOI:10.1364/OME.3.000711
  • Yadavalli NS, Linde F, Kopyshev A, et al. Soft matter beats hard matter: rupturing of thin metallic films induced by mass transport in photosensitive polymer films. ACS Appl Mater Interfaces. 2013;5(16):7743–7747. DOI:10.1021/am400682w
  • König T, Tsukruk VV, Santer S. Controlled topography change of subdiffraction structures based on photosensitive polymer films induced by surface plasmon polaritons. ACS Appl Mater Interfaces. 2013;5(13):6009–6016.
  • Tomczyk J, Sobolewska A, Nagy ZT, et al. Photo- and thermal-processing of azobenzene-containing star-shaped liquid crystals. J Mater Chem C. 2013;1(5):924–932. DOI:10.1039/C2TC00627H
  • Florio GD, Bründermann E, Yadavalli NS, et al. Graphene multilayer as nanosized optical strain gauge for polymer surface relief gratings. Nano Lett. 2014;14(10):5754–5760. DOI:10.1021/nl502631s
  • Koskela JE, Vapaavuori J, Ras RHA, et al. Light-driven surface patterning of supramolecular polymers with extremely low concentration of photoactive molecules. ACS Macro Lett. 2014;3(11):1196–1200. DOI:10.1021/mz500616q
  • Wei R, Xu Z, Wang X. Epoxy-based azo polymer for photofabricating surface-relief quasi-crystal structures. Opt Mater Express. 2015;5(6):1348.
  • Kopyshev A, Galvin CJ, Patil RR, et al. Light-induced reversible change of roughness and thickness of photosensitive polymer brushes. ACS Appl Mater Interfaces. 2016;8(29):19175–19184. DOI:10.1021/acsami.6b06881
  • Wang X, Vapaavuori J, Wang X, et al. Influence of supramolecular interaction type on photoresponsive azopolymer complexes: a surface relief grating formation study. Macromolecules. 2016;49(13):4923–4934. DOI:10.1021/acs.macromol.6b01009
  • Bedrov D, Hooper JB, Glaser MA, et al. Photoinduced and thermal relaxation in surface-grafted azobenzene-based monolayers: a molecular dynamics simulation study. Langmuir. 2016;32(16):4004–4015. DOI:10.1021/acs.langmuir.6b00120
  • Pedersen TG, Johansen PM, Holme NCR, et al. Mean-field theory of photoinduced formation of surface reliefs in side-chain azobenzene polymers. Phys Rev Lett. 1998;80(1):89–92. DOI:10.1103/PhysRevLett.80.89
  • Frascella F, Angelini A, Ricciardi S, et al. Surface-relief formation in azo-polyelectrolyte layers with a protective polymer coating. Opt Mater Express. 2016;6(2):444. DOI:10.1364/OME.6.000444
  • Kim CB, Wistrom JC, Ha H, et al. Marangoni instability driven surface relief grating in an azobenzene-containing polymer film. Macromolecules. 2016;49(18):7069–7076. DOI:10.1021/acs.macromol.6b01848
  • Noga J, Sobolewska A, Bartkiewicz S, et al. Periodic surface structures induced by a single laser beam irradiation. Macromol Mater Eng. 2017;302(2):1600329. DOI:10.1002/mame.201600329
  • Lomadze N, Kopyshev A, Bargheer M, et al. Mass production of polymer nano-wires filled with metal nano-particles. Sci Rep. 2017;7(1):8506. DOI:10.1038/s41598-017-08153-0
  • Hendrikx M, Ter Schiphorst J, van Heeswijk EPA, et al. Re- and preconfigurable multistable visible light responsive surface topographies. Small. 2018;14(50):1803274. DOI:10.1002/smll.201803274
  • Vapaavuori J, Bazuin CG, Priimagi A. Supramolecular design principles for efficient photoresponsive polymer–azobenzene complexes. J Mater Chem C. 2018;6(9):2168–2188.
  • Oscurato SL, Salvatore M, Borbone F, et al. Computer-generated holograms for complex surface reliefs on azopolymer films. Sci Rep. 2019;9(1):6775. DOI:10.1038/s41598-019-43256-w
  • Kim K, Park H, Park KJ, et al. Light-directed soft mass migration for micro/nanophotonics. Adv Opt Mater. 2019;7(16):1900074. DOI:10.1002/adom.201900074
  • Jelken J, Santer S. Light induced reversible structuring of photosensitive polymer films. RSC Adv. 2019;9(35):20295–20305.
  • Kumar J, Li L, Jiang XL, et al. Gradient force: the mechanism for surface relief grating formation in azobenzene functionalized polymers. Appl Phys Lett. 1998;72:2096–2098.
  • Vapaavuori J, Stimpson TC, Moran-Mirabal JM. Dynamically evolving surface patterns through light-triggered wrinkling erasure. Langmuir. 2019;35(4):875–881.
  • Spiridon MC, Demazy N, Brochon C, et al. Optical alignment of Si-containing nanodomains formed by photoresponsive amorphous block copolymer thin films. Macromolecules. 2020;53(1):68–77. DOI:10.1021/acs.macromol.9b01551
  • Salvatore M, Borbone F, Oscurato SL. Deterministic realization of quasicrystal surface relief gratings on thin azopolymer films. Adv Mater Interfaces. 2020;7(11):1902118.
  • Miniewicz A, Sobolewska A, Piotrowski W, et al. Thermocapillary marangoni flows in azopolymers. Materials. 2020;13(11):2464. DOI:10.3390/ma13112464
  • Chen J, Xu T, Zhao W, et al. Photoresponsive thin films of well-synthesized azobenzene side-chain liquid crystalline polynorbornenes as command surface for patterned graphic writing. Polymer. 2021;218:123492.
  • Feng W, Chu L, de Rooij MB, et al. Photoswitching between water-tolerant adhesion and swift release by inverting liquid crystal fingerprint topography. Adv Sci. 2021;8(8):2004051. DOI:10.1002/advs.202004051
  • Bian S, Li L, Kumar J, et al. Single laser beam-induced surface deformation on azobenzene polymer films. Appl Phys Lett. 1998;73:1817–1819.
  • Viswanathan NK, Balasubramanian S, Li L, et al. Surface-initiated mechanism for the formation of relief gratings on azo-polymer films. J Phys Chem B. 1998;102(31):6064–6070. DOI:10.1021/jp981425z
  • Fong WK, Malic N, Evans RA, et al. Alkylation of spiropyran moiety provides reversible photo-control over nanostructured soft materials. Biointerphases. 2012;7(1):3–7. DOI:10.1007/s13758-011-0003-9
  • Ito M, Ubukata T. Photoconstruction of a microrelief in a photochromic crystalline spirooxazine film. Chem Lett. 2019;48(1):32–35.
  • Mele E, Pisignano D, Varda M, et al. Smart photochromic gratings with switchable wettability realized by green-light interferometry. Appl Phys Lett. 2006;88(20):203124. DOI:10.1063/1.2198509
  • Ubukata T, Takahashi K, Yokoyama Y. Photoinduced surface relief structures formed on polymer films doped with photochromic spiropyrans. J Phys Org Chem. 2007;20(11):981–984.
  • Ubukata T, Fujii S, Arimatsu K, et al. Phototriggered micromanufacturing using photoresponsive amorphous spirooxazine films. J Mater Chem. 2012;22(29):14410–14417. DOI:10.1039/c2jm32149a
  • Ubukata T, Yamaguchi S, Yokoyama Y. Photoinduced surface relief structures formed on polymer films mixed with diarylethenes. Chem Lett. 2007;36(10):1224–1225.
  • Kikuchi A, Harada Y, Yagi M, et al. Photoinduced diffusive mass transfer in o-Cl-HABI amorphous thin films. Chem Commun. 2010;46(13):2262–2264. DOI:10.1039/b919180a
  • Park JW, Nagano S, Yoon SJ, et al. High contrast fluorescence patterning in cyanostilbene-based crystalline thin films: crystallization-induced mass flow via a photo-triggered phase transition. Adv Mater. 2014;26(9):1354–1359. DOI:10.1002/adma.201304250
  • Zhao D, Xu Z, Wang G, et al. Formation of surface relief gratings with homeotropically oriented photopolymer from a photocross-linkable organic monomer. Phys Chem Chem Phys. 2010;12(7):1436–1439. DOI:10.1039/B919659E
  • Ono H, Emoto A, Kawatsuki N, et al. Self-organized phase gratings in photoreactive polymer liquid crystals. Appl Phys Lett. 2003;82(9):1359–1361. DOI:10.1063/1.1557327
  • Ono H, Hatayama A, Emoto A, et al. Migration induced reorientation and anisotropic grating formation in photoreactive polymer liquid crystals. Opt Mater. 2007;30(2):248–254. DOI:10.1016/j.optmat.2006.11.048
  • Emoto A, Matsumoto T, Yamashita A, et al. Large birefringence and polarization holographic gratings formed in photocross-linkable polymer liquid crystals comprising bistolane mesogenic side groups. J Appl Phys. 2009;106(7):073505. DOI:10.1063/1.3234385
  • Kawatsuki N, Matsushita H, Kondo M, et al. Photoinduced reorientation and polarization holography in a new photopolymer with 4-methoxy-N-benzylideneaniline side groups. APL Mater. 2013;1(2):022103. DOI:10.1063/1.4818003
  • Okano K, Ogino S, Kawamoto M, et al. Mass migration on a polymer surface caused by photoinduced molecular rotation. Chem Commun. 2011;47(43):11891–11893. DOI:10.1039/c1cc14375a
  • Ubukata T, Seki T, Ichimura K. Surface relief gratings in host-guest supramolecular materials. Adv Mater. 2000;12(22):1675–1678.
  • Zettsu N, Ubukata T, Seki T, et al. Soft crosslinkable azo polymer for rapid surface relief formation and persistent fixation. Adv Mater. 2001;13(22):1693–1697. DOI:10.1002/1521-4095(200111)13:22<1693:AID-ADMA1693>3.0.CO;2-2
  • Zettsu N, Ogasawara T, Arakawa R, et al. Highly photosensitive surface relief gratings formation in a liquid crystalline azobenzene polymer: new implications for the migration process. Macromolecules. 2007;40:4607–4613.
  • Zettsu N, Ogasawara T, Mizoshita N, et al. Photo-triggered surface relief grating formation in supramolecular liquid crystalline polymer systems with detachable azobenzene units. Adv Mater. 2008;20(3):516–521. DOI:10.1002/adma.200701110
  • Nishizawa K, Nagano S, Seki T. Novel liquid crystalline organic−inorganic hybrid for highly sensitive photoinscriptions. Chem Mater. 2009;21(13):2624–2631.
  • Nishizawa K, Nagano S, Seki T. Micropatterning of titanium oxide film via phototactic mass transport. J Mater Chem. 2009;19(39):7191–7194.
  • Li W, Nagano S, Seki T. Photo-crosslinkable liquid-crystalline azo-polymer for surface relief gratings and persistent fixation. New J Chem. 2009;33(6):1343–1348.
  • Isayama J, Nagano S, Seki T. Phototriggered mass migrating motions in liquid crystalline azobenzene polymer films with systematically varied thermal properties. Macromolecules. 2010;43(9):4105–4112.
  • Li W, Dohi T, Hara M, et al. Phototriggered mass migration consorted with surface dewetting in thin films of a liquid crystalline azobenzene-containing dendrimer. Macromolecules. 2012;45(16):6618–6627. DOI:10.1021/ma301170x
  • Seki T. Meso- and microscopic motions in photoresponsive liquid crystalline polymer films. Macromol Rapid Commun. 2014;35:271–290.
  • Mitsui S, Nagano S, Hara M, et al. SRG inscription in supramolecular liquid crystalline polymer film: replacement of mesogens. Crystals. 2017;7(2):52. DOI:10.3390/cryst7020052
  • Beppu K, Nagashima Y, Hara M, et al. Photoalignment of vertically oriented microphase separated lamellae in LC–LC diblock copolymer thin film. Macromol Rapid Commun. 2017;38(13):1600659. DOI:10.1002/marc.201600659
  • Zettsu N, Ubukata T, Seki T, et al. Azo polymers with oligo(ethylene oxide) side chain for rapid surface relief formation. J Photopolym Sci Technol. 2001;14(2):193–194. DOI:10.2494/photopolymer.14.193
  • Kitamura I, Oishi K, Hara M, et al. Photoinitiated marangoni flow morphing in a liquid crystalline polymer film directed by super-inkjet printing patterns. Sci Rep. 2019;9(1):2556. DOI:10.1038/s41598-019-38709-1
  • Kitamura I, Kato K, Berk RB, et al. Photo-triggered large mass transport driven only by a photoresponsive surface skin layer. Sci Rep. 2020;10(1):12664. DOI:10.1038/s41598-020-69605-8
  • Yamakado R, Kitamura I, Hara M, et al. Photoisomerization-induced patterning of ion-pairing materials based on anionic azobenzene and its complex with a fluorescent π-electronic system. Chem Commun. 2021;57(35):4287–4290. DOI:10.1039/D0CC07640F
  • Zhang D, Liu D, Ubukata T, et al. Unconventional approaches to light-promoted dynamic surface morphing on polymer films. Bull Chem Soc Jpn. 2022;95(1):138–162. DOI:10.1246/bcsj.20210348
  • Ubukata T, Seki T, Ichimura K. Surface relief grating in hybrid films composed of azobenzene polymer and liquid crystal molecule. Colloids Surf A Physicochem Eng Asp. 2002;198–200:113–117.
  • Ubukata T, Hara M, Seki T. Photogeneration of surface relief gratings in azobenzene polymer/liquid crystal hybrid films. Mol Cryst Liq Cryst. 2002;377(1):173–176.
  • Ubukata T, Hara M, Ichimura K, et al. Phototactic mass transport in polymer films for micropatterning and alignment of functional materials. Adv Mater. 2004;16(3):220–223. DOI:10.1002/adma.200305535
  • Zettsu N, Ubukata T, Seki T. Two-dimensional manipulation of poly(3-dodecylthiophene) using light-driven instant mass migration as a molecular conveyer. Japanese J Appl Physics. 2004;43(No. 9A/B):L1169–1171. Part 2 Lett. DOI:10.1143/JJAP.43.L1169.
  • Zettsu N, Seki T. Highly efficient photogeneration of surface relief structure and its immobilization in cross-linkable liquid crystalline azobenzene polymers. Macromolecules. 2004;37(23):8692–8698.
  • Ubukata T, Higuchi T, Zettsu N, et al. Spontaneous motion observed in highly sensitive surface relief formation system. Colloids Surf A Physicochem Eng Asp. 2005;257-258:123–126.
  • Seki T. Photoresponsive self-assembly motions in polymer thin films. Curr Opin Solid State Mater Sci. 2006;10(5–6):241–248.
  • Kopyshev A, Kanevche K, Lomadze N, et al. Light-induced structuring of photosensitive polymer brushes. ACS Appl Polym Mater. 2019;1(11):3017–3026. DOI:10.1021/acsapm.9b00705
  • Yoneyama S, Yamamoto T, Tsutsumi O, et al. High-performance material for holographic gratings by means of a photoresponsive polymer liquid crystal containing a tolane moiety with high birefringence. Macromolecules. 2002;35(23):8751–8758. DOI:10.1021/ma020886m
  • Yamamoto T, Hasegawa M, Kanazawa A, et al. Holographic gratings and holographic image storage via photochemical phase transitions of polymer azobenzene liquid-crystal films. J Mater Chem. 2000;10(2):337–342. DOI:10.1039/a905501k
  • Yamamoto T, Yoneyama S, Tsutsumi O, et al. Holographic gratings in the optically isotropic state of polymer azobenzene liquid-crystal films. J Appl Phys. 2000;88(5):2215–2220. DOI:10.1063/1.1287761
  • Shishido A, Ishiguro M, Ikeda T. Circular arrangement of mesogens induced in Bragg-type polarization holograms of thick azobenzene copolymer films with a tolane moiety. Chem Lett. 2007;36(9):1146–1147.
  • Ishiguro M, Sato D, Shishido A, et al. Bragg-type polarization gratings formed in thick polymer films containing azobenzene and tolane moieties. Langmuir. 2007;23(1):332–338. DOI:10.1021/la061587j
  • Bang CU, Shishido A, Ikeda T. Azobenzene liquid-crystalline polymer for optical switching of grating waveguide couplers with a flat surfacea. Macromol Rapid Commun. 2007;28(9):1040–1044.
  • Ikeda T, Yoneyama S, Yamamoto T, et al. Holographic grating by means of polymer liquid crystals. J Inf Disp. 2001;2(3):6–12. DOI:10.1080/15980316.2001.9651860
  • Hasegawa M, Yamamoto T, Kanazawa A, et al. Real-time holographic grating by means of photoresponsive polymer liquid crystals with a flexible siloxane spacer in the side chain. J Mater Chem. 1999;9(11):2765–2769. DOI:10.1039/a903948a
  • Hasegawa M, Yamamoto T, Kanazawa A, et al. A dynamic grating using a photochemical phase transition of polymer liquid crystals containing azobenzene derivatives. Adv Mater. 1999;11(8):675–677. DOI:10.1002/(SICI)1521-4095(199906)11:8<675:AID-ADMA675>3.0.CO;2-Z
  • Yamamoto T, Hasegawa M, Kanazawa A, et al. Phase-type gratings formed by photochemical phase transition of polymer azobenzene liquid crystals: enhancement of diffraction efficiency by spatial modulation of molecular alignment. J Phys Chem B. 1999;103(45):9873–9878. DOI:10.1021/jp992172s
  • Tsutsumi O, Ikeda T. Photochemical modulation of alignment of liquid crystals and photonic applications. Curr Opin Solid State Mater Sci. 2002;6(6):563–568.
  • Shishido A, Cha H-B, Ikeda T. Rewritable bragg holograms of azobenzene polymers with fast response. Liq Cryst. 2009 XIII(7414):74140S.
  • Ishii N, Kato T, Abe J. A real-time dynamic holographic material using a fast photochromic molecule. Sci Rep. 2012;2(1):819.
  • Kobayashi Y, Abe J. Real-time dynamic hologram of a 3D object with fast photochromic molecules. Adv Opt Mater. 2016;4(9):1354–1357.
  • Wang H, Pumera M. Fabrication of micro/nanoscale motors. Chem Rev. 2015;115(16):8704–8735.
  • Tu Y, Peng F, Wilson DA. Motion manipulation of micro- and nanomotors. Adv Mater. 2017;29(39):1701970.
  • Eskandarloo H, Kierulf A, Abbaspourrad A. Light-harvesting synthetic nano- and micromotors: a review. Nanoscale. 2017;9:12218–12230.
  • Xu L, Mou F, Gong H, et al. Light-driven micro/nanomotors: from fundamentals to applications. Chem Soc Rev. 2017;46(22):6905–6926. DOI:10.1039/C7CS00516D
  • Kuwahara Y, Oda T, Kim S, et al. Photo-responsive traveling of small-particles modified with azobenzene groups as molecular motors in a liquid crystal. Mater Lett. 2016;181:257–260.
  • Uchida E, Azumi R, Norikane Y. Light-induced crawling of crystals on a glass surface. Nat Commun. 2015;6(1):7310.
  • Nakano H. Direction control of photomechanical bending of a photochromic molecular fiber. J Mater Chem. 2010;20(11):2071–2074.
  • Norikane Y, Hayashino M, Ohnuma M, et al. Photo-induced crawling motion of azobenzene crystals on modified gold surfaces. Langmuir. 2021;37(48):14177–14185. DOI:10.1021/acs.langmuir.1c02494
  • Muto M, Ayako Y, Yamamoto K, et al. Photochemical migration of liquid column in a glass tube. Eur Phys J Spec Top. 2017;226(6):1199–1205. DOI:10.1140/epjst/e2016-60217-y
  • Norikane Y, Hayashino M, Ohnuma M, et al. Effect of surface properties on the photo-induced crawling motion of azobenzene crystals on glass surfaces. Front Chem. 2021;9:684767.
  • Suzuki M, Nakano H. Moving fragments of photochromic molecuar glass of 4-[bis(9,9-dimethylfluoren-2-yl)amino]-4′-cyanoazobenzene. J Photopolym Sci Technol. 2012;25(2):159–160.
  • Lin G, Richardson JJ, Ahmed H, et al. Programmable phototaxis of metal–phenolic particle microswimmers. Adv Mater. 2021;33(13):2006177. DOI:10.1002/adma.202006177
  • Nakano H, Suzuki M. Photoinduced mass flow of photochromic molecular materials. J Mater Chem. 2012;22(9):3702–3704.
  • Ichikawa R, Nakano H. Photoinduced change in the shape of azobenzene-based molecular glass particles fixed in agar gel. RSC Adv. 2016;6(43):36761–36765.
  • Matsubara M, Ukai H, Kuragano M, et al. Chiral photomechanical behavior of achiral azobenzene-based molecular glass particles fixed in agar gel. Chem Lett. 2022;51(5):493–496. DOI:10.1246/cl.220054
  • Liu GL, Kim J, Lu YU, et al. Optofluidic control using photothermal nanoparticles. Nat Mater. 2006;5(1):27–32. DOI:10.1038/nmat1528
  • Kaneko S, Asakura K, Banno T. Phototactic behavior of self-propelled micrometer-sized oil droplets in a surfactant solution. Chem Commun. 2017;53(14):2237–2240.
  • Nitta K, Tsukahara T. Numerical demonstration of in-tube liquid-column migration driven by photoisomerization. Micromach. 2018;9(10):533.
  • Eelkema R, Pollard MM, Katsonis N, et al. Rotational reorganization of doped cholesteric liquid crystalline films. J Am Chem Soc. 2006;128(44):14397–14407. DOI:10.1021/ja065334o
  • Kausar A, Nagano H, Okada S, et al. Micro manipulation with optical responsive cholesteric and compensated nematic liquid crystal. Mol Cryst Liq Cryst. 2009;513(1):122–130. DOI:10.1080/15421400903196112
  • Mafy NN, Kim Y, Thomas R, et al. Molecular crankshaft effect converting piston-like molecular motion to continuous rotation of macro objects. ACS Appl Mater Interfaces. 2019;11(16):15097–15102. DOI:10.1021/acsami.9b03706
  • Kim Y, Mafy NN, Maisonneuve S, et al. Glycomacrocycle-based azobenzene derivatives as chiral dopants for photoresponsive cholesteric liquid crystals. ACS Appl Mater Interfaces. 2020;12(46):52146–52155. DOI:10.1021/acsami.0c14880
  • Eelkema R, Pollard MM, Vicario J, et al. Nanomotor rotates microscale objects. Nature. 2006;440(7081):163. DOI:10.1038/440163a
  • Tamaoki N, Kamei T. Reversible photo-regulation of the properties of liquid crystals doped with photochromic compounds. J Photochem Photobiol C Photochem Rev. 2010;11(2–3):47–61.
  • Jau HC, Lin TH, Chen YY, et al. Direction switching and beam steering of cholesteric liquid crystal gratings. Appl Phys Lett. 2012;100(13):131909. DOI:10.1063/1.3698384
  • Thomas R, Yoshida Y, Akasaka T, et al. Influence of a change in helical twisting power of photoresponsive chiral dopants on rotational manipulation of micro-objects on the surface of chiral nematic liquid crystalline films. Chem - A Eur J. 2012;18(39):12337–12348. DOI:10.1002/chem.201200836
  • Ma S, Kuwahara Y, Nagano H, et al. Photo-controlled manipulation of micrometer-scale objects on polyethyleneglycol thin films with azobenzene compounds. Mol Cryst Liq Cryst. 2014;601(1):126–133. DOI:10.1080/15421406.2014.944382
  • Kim Y, Tamaoki N. A photoresponsive planar chiral azobenzene dopant with high helical twisting power. J Mater Chem C. 2014;2(43):9258–9264.
  • Kim Y, Tamaoki N. Asymmetric dimers of chiral azobenzene dopants exhibiting unusual helical twisting power upon photoswitching in cholesteric liquid crystals. ACS Appl Mater Interfaces. 2016;8(7):4918–4926.
  • Wu ZL, Wang ZJ, Keller P, et al. Light responsive microstructured surfaces of liquid crystalline network with shape memory and tunable wetting behaviors. Macromol Rapid Commun. 2016;37(4):311–317. DOI:10.1002/marc.201500533
  • Kim Y, Frigoli M, Vanthuyne N, et al. A helical naphthopyran dopant for photoresponsive cholesteric liquid crystals. Chem Commun. 2017;53(1):200–203. DOI:10.1039/C6CC08667E
  • Mathews M, Tamaoki N. Planar chiral azobenzenophanes as chiroptic switches for photon mode reversible reflection color control in induced chiral nematic liquid crystals. J Am Chem Soc. 2008;130(34):11409–11416.
  • Li Y, Li Q. Photochemically reversible and thermally stable axially chiral diarylethene switches. Org Lett. 2012;14(17):4362–4365.
  • Kausar A, Nagano H, Kuwahara Y, et al. Photocontrolled manipulation of a microscale object: a rotational or translational mechanism. Chem Eur J. 2011;17(2):508–515. DOI:10.1002/chem.201001238
  • Ichimura K, Oh S-K, Nakagawa M. Light-driven motion of liquids on a photoresponsive surface. Science. 2000;288:1624–1626.
  • Oh SK, Nakagawa M, Ichimura K. Photocontrol of liquid motion on an azobenzene monolayer. J Mater Chem. 2002;12(8):2262–2269.
  • Monobe H, Ohzono T, Akiyama H, et al. Manipulation of liquid filaments on photoresponsive microwrinkles. ACS Appl Mater Interfaces. 2012;4(4):2212–2217. DOI:10.1021/am300225m
  • Zhu F, Tan S, Dhinakaran MK, et al. The light-driven macroscopic directional motion of a water droplet on an azobenzene–calix[4]arene modified surface. Chem Commun. 2020;56(74):10922–10925. DOI:10.1039/D0CC00519C
  • De Jong E, Kremer R, Liu L, et al. Mechanowetting drives droplet and fluid transport on traveling surface waves generated by light-responsive liquid crystal polymers. Phys Fluids. 2021;33(6):063307. DOI:10.1063/5.0050864
  • Yamamoto T, Yamamoto J, Lev BI, et al. Light-induced assembly of tailored droplet arrays in nematic emulsions. Appl Phys Lett. 2002;81(12):2187–2189. DOI:10.1063/1.1508816
  • Diguet A, Guillermic RM, Magome N, et al. Photomanipulation of a droplet by the chromocapillary effect. Angew Chem Int Ed. 2009;48(49):9281–9284. DOI:10.1002/anie.200904868
  • Kausar A, Nagano H, Ogata T, et al. Photocontrolled translational motion of a microscale solid object on azobenzene-doped liquid-crystalline films. Angew Chem Int Ed. 2009;48(12):2144–2147. DOI:10.1002/anie.200804762
  • Varanakkottu SN, George SD, Baier T, et al. Particle manipulation based on optically controlled free surface hydrodynamics. Angew Chem Int Ed. 2013;52(28):7291–7295. DOI:10.1002/anie.201302111
  • Kavokine N, Anyfantakis M, Morel M, et al. Light-driven transport of a liquid marble with and against surface flows. Angew Chem Int Ed. 2016;55(37):11183–11187. DOI:10.1002/anie.201603639
  • Rossegger E, Hennen D, Griesser T, et al. Directed motion of water droplets on multi-gradient photopolymer surfaces. Polym Chem. 2019;10(15):1882–1893. DOI:10.1039/C9PY00123A
  • Xia J, Zhao P, Zheng K, et al. Surface modification based on diselenide dynamic chemistry: towards liquid motion and surface bioconjugation. Angew Chem. 2018;310036:552–556.
  • Berná J, Leigh DA, Lubomska M, et al. Macroscopic transport by synthetic molecular machines. Nat Mater. 2005;4(9):704–710. DOI:10.1038/nmat1455
  • Monteleone FV, Caputo G, Canale C, et al. Light-controlled directional liquid drop movement on TiO2 nanorods-based nanocomposite photopatterns. Langmuir. 2010;26(23):18557–18563. DOI:10.1021/la1026398
  • Rossegger E, Nees D, Turisser S, et al. Photo-switching of surface wettability on micropatterned photopolymers for fast transport of water droplets over a long-distance. Polym Chem. 2020;11(18):3125–3135. DOI:10.1039/D0PY00263A
  • Xu B, Zhu C, Qin L, et al. Light-directed liquid manipulation in flexible bilayer microtubes. Small. 2019;15(24):1901847. DOI:10.1002/smll.201901847
  • Liu Q, Yu G, Zhu C, et al. An Integrated droplet manipulation platform with photodeformable microfluidic channels. Small Methods. 2021;5(12):2100969. DOI:10.1002/smtd.202100969
  • Ji S, Cao W, Yu Y, et al. Dynamic diselenide bonds: exchange reaction induced by visible light without catalysis. Angew Chem Int Ed. 2014;53(26):6781–6785. DOI:10.1002/anie.201403442
  • Ji S, Xia J, Xu H. Dynamic chemistry of selenium: Se–N and Se–Se dynamic covalent bonds in polymeric systems. ACS Macro Lett. 2016;5(1):78–82.
  • Xia J, Ji S, Xu H. Diselenide covalent chemistry at the interface: stabilizing an asymmetric diselenide-containing polymer via micelle formation. Polym Chem. 2016;7(44):6708–6713.
  • Voloshchenko D, Khyzhnyak A, Reznikov Y, et al. Control of an easy axis on a nematic-polymer interface by a light action to a nematic bulk. Jpn J Appl Phys. 1995;34(Part 1, No. 2A):566. DOI:10.1143/JJAP.34.566
  • Slussarenko S, Francescangeli O, Simoni F, et al. High resolution polarization gratings in liquid crystals. Appl Phys Lett. 1997;71(25):3613–3615. DOI:10.1063/1.120457
  • Simoni F, Francescangeli O, Reznikov Y, et al. Dye-doped liquid crystals as high-resolution recording media: errata. Opt Lett. 1997;22(12):937. DOI:10.1364/OL.22.000937
  • Francescangeli O, Slussarenko S, Simoni F, et al. Light-induced surface sliding of the nematic director in liquid crystals. Phys Rev Lett. 1999;82(9):1855–1858. DOI:10.1103/PhysRevLett.82.1855
  • Simoni F, Francescangeli O. Effects of light on molecular orientation of liquid crystals. J Phys Condens Matter. 1999;11(41):439–487.
  • Motevalli B, Taherifar N, Wu B, et al. A density functional theory computational study of adsorption of di-meta-cyano azobenzene molecules on Si (111) surfaces. Appl Surf Sci. 2017;422:557–565.
  • Komitov L, Ruslim C, Matsuzawa Y, et al. Photoinduced anchoring transitions in a nematic doped with azo dyes. Liq Cryst. 2000;27(8):1011–1016. DOI:10.1080/02678290050080733
  • Komitov L, Ichimura K, Strigazzi A. Light-induced anchoring transition in a 4,4’-disubstituted azobenzene nematic liquid crystal. Liq Cryst. 2000;27(1):51–55.
  • Ruslim C, Komitov L, Matsuzawa Y, et al. Effect of conformations of trans- and cis-azobenzenes on photoinduced anchoring transitions in a nematic liquid crystal. Japanese J Appl Physics. 2000;39(Part 2, No. 2A):L104–106. Part 2 Lett:
  • Lee C-H, Chen C-H, Kao C-L, et al. Photo and electrical tunable effects in photonic liquid crystal fiber. Opt Express. 2010;18(3):2814. DOI:10.1364/OE.18.002814
  • Ouskova E, Vapaavuori J, Kaivola M. Self-orienting liquid crystal doped with polymer-azo-dye complex. Opt Mater Express. 2011;1(8):1463.
  • Yang K-Y, Lee W. Voltage-assisted photoaligning effect of an azo dye doped in a liquid crystal with negative dielectric anisotropy. Opt Express. 2010;18(19):19914.
  • Shen Y, Xu Y-C, Ge Y-H, et al. Photoalignment of dye-doped cholesteric liquid crystals for electrically tunable patterns with fingerprint textures. Opt Express. 2018;26(2):1422. DOI:10.1364/OE.26.001422
  • Lee CR, Fu TL, Cheng KT, et al. Surface-assisted photoalignment in dye-doped liquid-crystal films. Phys Rev E. 2004;69(3):031704. DOI:10.1103/PhysRevE.69.031704
  • Chen CH, Lee CH, Lin TH. Loss-reduced photonic liquid-crystal fiber by using photoalignment method. Appl Opt. 2010;49(26):4846–4850.
  • Fuh A-G, Liao C-C, Hsu K-C, et al. Laser-induced reorientation effect and ripple structure in dye-doped liquid-crystal films. Opt Lett. 2003;28(14):1179. DOI:10.1364/OL.28.001179
  • Lee CR, Mo TS, Cheng KT, et al. Electrically switchable and thermally erasable biphotonic holographic gratings in dye-doped liquid crystal films. Appl Phys Lett. 2003;83(21):4285–4287. DOI:10.1063/1.1629374
  • Chen WZ, Tsai YT, Lin TH. Photoalignment effect in a liquid-crystal film doped with nanoparticles and azo-dye. Appl Phys Lett. 2009;94(20):201114.
  • Fuh AYG, Chen JC, Huang SY, et al. Binary liquid crystal alignments based on photoalignment in azo dye-doped liquid crystals and their application. Appl Phys Lett. 2010;96(5):2008–2011. DOI:10.1063/1.3299268
  • Wu WY, Fuh AYG. Rewritable liquid crystal gratings fabricated using photoalignment effect in dye-doped poly(vinyl alcohol) film. Jpn J Appl Phys. 2007;46(10A):6761–6766.
  • Khoo IC, Wood M, Shih MY, et al. Extremely nonlinear photosensitive liquid crystals for image sensing and sensor protection. Opt Express. 1999;4(11):432. DOI:10.1364/OE.4.000432
  • Lin TH, Jau HC, Hung SY, et al. Photoaddressable bistable reflective liquid crystal display. Appl Phys Lett. 2006;89(2):021116. DOI:10.1063/1.2219406
  • Lin L-C, Jau H-C, Lin T-H, et al. Highly efficient and polarization-independent fresnel lens based on dye-doped liquid crystal. Opt Express. 2007;15(6):2900–2906. DOI:10.1364/OE.15.002900
  • Khoo IC, Shih M-Y, Wood MV, et al. Dye-doped photorefractive liquid crystals for dynamic and storage holographic grating formation and spatial light modulation. Proc IEEE. 1999;87(11):1897–1911. DOI:10.1109/5.796353
  • Wang C-T, Jau H-C, Lin T-H. Optically controllable bistable reflective liquid crystal display. Opt Lett. 2012;37(12):2370.
  • Huang SY, Wu ST, Fuh AYG. Optically switchable twist nematic grating based on a dye-doped liquid crystal film. Appl Phys Lett. 2006;88(4):041104.
  • Wu W-Y, Mo T-S, Fuh A-G. Polarization characteristics of diffracted beams from twisted nematic gratings fabricated by the photoalignment effect in dye-doped liquid-crystal films. J Opt Soc Am B. 2006;23(9):1737.
  • Fuh A-G, Chen J-C, Cheng K-T, et al. Polarization-independent and electrically tunable liquid-crystal fresnel lenses based on photoalignment in dye-doped liquid crystals. J Soc Inf Disp. 2010;18(8):572. DOI:10.1889/JSID18.8.572
  • Huang Y, Ko S, Chu S, et al. High-efficiency fresnel lens fabricated by axially symmetric photoalignment method. Appl Opt. 2012;51(32):7739–7744. DOI:10.1364/AO.51.007739
  • Okabe Y, Ogawa M. Photoinduced adsorption of spiropyran into mesoporous silicas as photomerocyanine. RSC Adv. 2015;5(123):101789–101793.
  • Yamaguchi T, Maity A, Polshettiwar V, et al. Photochromism of a spiropyran in the presence of a dendritic fibrous nanosilica; simultaneous photochemical reaction and adsorption. J Phys Chem A. 2017;121(42):8080–8085. DOI:10.1021/acs.jpca.7b08466
  • Yamaguchi T, Leelaphattharaphan NN, Shin H, et al. Acceleration of photochromism and negative photochromism by the interactions with mesoporous silicas. Photochem Photobiol Sci. 2019;18(7):1742–1749. DOI:10.1039/C9PP00081J
  • Yamaguchi T, Ogawa M. Photochromism of a spiropyran in the presence of a synthetic hectorite. Chem Lett. 2018;47(2):189–191.
  • Leelaphattharaphan NN, Deepracha SB, Yamaguchi T, et al. Adsorption of a spiropyran on a layered clay mineral. IOP Conf Ser Earth Environ Sci. 2022;950(1):012041. DOI:10.1088/1755-1315/950/1/012041
  • Colaço M, Carletta A, Van Gysel M, et al. Direct access by mechanochemistry or sonochemistry to protonated merocyanines: components of a four-state molecular switch. ChemistryOpen. 2018;7(7):520–526. DOI:10.1002/open.201800082
  • Wang Y, Li B, Zhang L, et al. Targeted delivery system based on magnetic mesoporous silica nanocomposites with light-controlled release character. ACS Appl Mater Interfaces. 2013;5(1):11–15. DOI:10.1021/am302492e
  • Angelos S, Choi E, Vögtle F, et al. Photo-driven expulsion of molecules from mesostructured silica nanoparticles. J Phys Chem C. 2007;111(18):6589–6592. DOI:10.1021/jp070721l
  • Lu J, Choi E, Tamanoi F, et al. Light-activated nanoimpeller-controlled drug release in cancer cells. Small. 2008;4(4):421–426. DOI:10.1002/smll.200700903
  • Liu J, Bu W, Pan L, et al. NIR-triggered anticancer drug delivery by upconverting nanoparticles with integrated azobenzene-modified mesoporous silica. Angew Chem Int Ed. 2013;52(16):4375–4379. DOI:10.1002/anie.201300183
  • Duan Y, Wang Y, Li X, et al. Light-triggered nitric oxide (NO) release from photoresponsive polymersomes for corneal wound healing. Chem Sci. 2020;11(1):186–194. DOI:10.1039/C9SC04039K
  • Nehls EM, Rosales AM, Anseth KS. Enhanced user-control of small molecule drug release from a poly(ethylene glycol) hydrogel via azobenzene/cyclodextrin complex tethers. J Mater Chem B. 2016;4(6):1035–1039.
  • Huang Q, Bao C, Ji W, et al. Photocleavable coumarin crosslinkers based polystyrene microgels: phototriggered swelling and release. J Mater Chem. 2012;22(35):18275–18282. DOI:10.1039/c2jm33789d
  • Wang Z, Johns VK, Liao Y. Controlled release of fragrant molecules with visible light. Chem - A Eur J. 2014;20(45):14637–14640.
  • Jin Q, Mitschang F, Agarwal S. Biocompatible drug delivery system for photo-triggered controlled release of 5-fluorouracil. Biomacromolecules. 2011;12(10):3684–3691.
  • Wang H, Miao W, Wang F, et al. A self-assembled coumarin-anchored dendrimer for efficient gene delivery and light-responsive drug delivery. Biomacromolecules. 2018;19(6):2194–2201. DOI:10.1021/acs.biomac.8b00246
  • Tan X, Li BB, Lu X, et al. Light-triggered, self-immolative nucleic acid-drug nanostructures. J Am Chem Soc. 2015;137(19):6112–6115. DOI:10.1021/jacs.5b00795
  • Bozuyuk U, Yasa O, Yasa IC, et al. Light-triggered drug release from 3D-printed magnetic chitosan microswimmers. ACS Nano. 2018;12(9):9617–9625. DOI:10.1021/acsnano.8b05997
  • Zang C, Wang H, Li T, et al. A light-responsive, self-immolative linker for controlled drug delivery via peptide- and protein-drug conjugates. Chem Sci. 2019;10(39):8973–8980. DOI:10.1039/C9SC03016F
  • Pei P, Sun C, Tao W, et al. ROS-sensitive thioketal-linked polyphosphoester-doxorubicin conjugate for precise phototriggered locoregional chemotherapy. Biomaterials. 2019;188:74–82.
  • Cui D, Huang J, Zhen X, et al. A semiconducting polymer nano-prodrug for hypoxia-activated photodynamic cancer therapy. Angew Chem Int Ed. 2019;58(18):5920–5924. DOI:10.1002/anie.201814730
  • Wu C, Chen C, Lai J, et al. Molecule-scale controlled-release system based on light-responsive silica nanoparticles. Chem Commun. 2008;23(23):2662–2664. DOI:10.1039/b804886j
  • Pelliccioli AP, Wirz J. Photoremovable protecting groups: reaction mechanisms and applications. Photochem Photobiol Sci. 2002;1(7):441–458.
  • Peng K, Tomatsu I, Kros A. Light controlled protein release from a supramolecular hydrogel. Chem Commun. 2010;46(23):4094–4096.
  • Pianowski ZL, Karcher J, Schneider K. Photoresponsive self-healing supramolecular hydrogels for light-induced release of DNA and doxorubicin. Chem Commun. 2016;52(15):3143–3146.
  • Liu XM, Yang B, Wang YL, et al. Photoisomerisable cholesterol derivatives as photo-trigger of liposomes: effect of lipid polarity, temperature, incorporation ratio, and cholesterol. Biochim Biophys Acta - Biomembr. 2005;1720(1–2):28–34. DOI:10.1016/j.bbamem.2005.10.016
  • Liu YC, Ny ALML, Schmidt J, et al. Photo-assisted gene delivery using light-responsive catanionic vesicles. Langmuir. 2009;25(10):5713–5724. DOI:10.1021/la803588d
  • Hu XY, Jia K, Cao Y, et al. Dual photo- and pH-responsive supramolecular nanocarriers based on water-soluble pillar[6]arene and different azobenzene derivatives for intracellular anticancer drug delivery. Chem - A Eur J. 2015;21(3):1208–1220. DOI:10.1002/chem.201405095
  • Liu H, Liu Y, Shang Y, et al. Molecular dynamics simulation for drug delivery in azobenzene-containing membranes. Mol Simul. 2020;46(4):300–307. DOI:10.1080/08927022.2019.1699655
  • Ishihara K, Negishi N, Shinohara I. Photoregulated binding ability of azoaromatic polymer for surfactant. J Polym Sci. 1981;19(12):3039–3046.
  • Ishihara K, Negishi N, Shinohara I. Photocontrolled adsorption chromatography for lysozyme using azoaromatic polymer. J Appl Polym Sci. 1982;27(6):1897–1902.
  • Kanj AB, Bürck J, Grosjean S, et al. Switching the enantioselectivity of nanoporous host materials by light. Chem Commun. 2019;55(60):8776–8779. DOI:10.1039/C9CC02849H
  • Ishihara K, Kato S, Shinohara I. Separation of proteins by polymeric adsorbents containing azobenzene moiety as a ligand. J Appl Polym Sci. 1982;27(11):4273–4282.
  • Wang Z, Grosjean S, Bräse S, et al. Photoswitchable adsorption in metal-organic frameworks based on polar guest-host interactions. Chemphyschem. 2015;16:3779–3783.
  • Puntoriero F, Ceroni P, Balzani V, et al. Photoswitchable dendritic hosts: a dendrimer with peripheral azobenzene groups. J Am Chem Soc. 2007;129(35):10714–10719. DOI:10.1021/ja070636r
  • Park J, Sun LB, Chen YP, et al. Azobenzene-functionalized metal-organic polyhedra for the optically responsive capture and release of guest molecules. Angew Chem Int Ed. 2014;53(23):5842–5846. DOI:10.1002/anie.201310211
  • Nakahara Y, Okazaki Y, Kimura K. Self-assembling phenomena of benzo-18-crown-6/crowned-spirobenzopyran copolymers in aqueous solution and controlled release of entrapped organic dyes using external stimuli. Soft Matter. 2012;8:3192–3199.
  • Wang X, Hu J, Liu G, et al. Reversibly switching bilayer permeability and release modules of photochromic polymersomes stabilized by cooperative noncovalent interactions. J Am Chem Soc. 2015;137(48):15262–15275. DOI:10.1021/jacs.5b10127
  • Chen S, Gao Y, Cao Z, et al. Nanocomposites of spiropyran-functionalized polymers and upconversion nanoparticles for controlled release stimulated by near-infrared light and pH. Macromolecules. 2016;49(19):7490–7496. DOI:10.1021/acs.macromol.6b01760
  • Müller K, Wadhwa J, Singh Malhi J, et al. Photoswitchable nanoporous films by loading azobenzene in metal–organic frameworks of type HKUST-1. Chem Commun. 2017;53(57):8070–8073. DOI:10.1039/C7CC00961E
  • Alvaro M, Benitez M, Das D, et al. Reversible porosity changes in photoresponsive azobenzene-containing periodic mesoporous silicas. Chem Mater. 2005;17:4958–4964.
  • Brown JW, Henderson BL, Kiesz MD, et al. Photophysical pore control in an azobenzene-containing metal-organic framework. Chem Sci. 2013;4:2858–2864.
  • Wang Z, Heinke L, Jelic J, et al. Photoswitching in nanoporous, crystalline solids: an experimental and theoretical study for azobenzene linkers incorporated in MOFs. Phys Chem Chem Phys. 2015;17(22):14582–14587. DOI:10.1039/C5CP01372K
  • Müller K, Knebel A, Zhao F, et al. Switching thin films of azobenzene-containing metal–organic frameworks with visible light. Chem Eur J. 2017;23(23):5434–5438. DOI:10.1002/chem.201700989
  • Zhang L, Wang LL, Le GL, et al. Coumarin-modified microporous-mesoporous Zn-MOF-74 showing ultra-high uptake capacity and photo-switched storage/release of UVI ions. J Hazard Mater. 2016;311:30–36.
  • Mal NK, Fujiwara M, Tanaka Y. Photocontrolled reversible release of guest molecules from coumarin-modified mesoporous silica. Nature. 2003;421(6921):350–353.
  • Mal NK, Fujiwara M, Tanaka Y, et al. Photo-switched storage and release of guest molecules in the pore void of coumarin-modified MCM-41. Chem Mater. 2003;15(17):3385–3394. DOI:10.1021/cm0343296
  • Chen L, Wang W, Su B, et al. A light-responsive release platform by controlling the wetting behavior of hydrophobic surface. ACS Nano. 2014;8(1):744–751. DOI:10.1021/nn405398d
  • Xing Q, Li N, Chen D, et al. Light-responsive amphiphilic copolymer coated nanoparticles as nanocarriers and real-time monitors for controlled drug release. J Mater Chem B. 2014;2(9):1182–1189. DOI:10.1039/c3tb21269f
  • Heinke L, Cakici M, Dommaschk M, et al. Photoswitching in two-component surface-mounted metal–organic frameworks: optically triggered release from a molecular container. ACS Nano. 2014;8(2):1463–1467. DOI:10.1021/nn405469g
  • Meng X, Gui B, Yuan D, et al. Mechanized azobenzene-functionalized zirconium metal-organic framework for on-command cargo release. Sci Adv. 2016;2(8):2–8. DOI:10.1126/sciadv.1600480
  • Mutruc D, Goulet-Hanssens A, Fairman S, et al. Modulating guest uptake in core–shell MOFs with visible light. Angew Chem Int Ed. 2019;58(37):12862–12867. DOI:10.1002/anie.201906606
  • Ou R, Zhang H, Zhao C, et al. Photoresponsive styrylpyrene-modified MOFs for gated loading and release of cargo molecules. Chem Mater. 2020;32(24):10621–10627. DOI:10.1021/acs.chemmater.0c03726
  • Zhu Y, Fujiwara M. Installing dynamic molecular photomechanics in mesopores: a multifunctional controlled-release nanosystem. Angew Chem Int Ed. 2007;46(13):2241–2244.
  • Ji W, Li N, Chen D, et al. Coumarin-containing photo-responsive nanocomposites for NIR light-triggered controlled drug release via a two-photon process. J Mater Chem B. 2013;1(43):5942–5949. DOI:10.1039/c3tb21206h
  • Yuan Q, Zhang Y, Chen T, et al. Photon-manipulated drug release from a mesoporous nanocontainer controlled by azobenzene-modified nucleic acid. ACS Nano. 2012;6(7):6337–6344. DOI:10.1021/nn3018365
  • Yan H, Teh C, Sreejith S, et al. Functional mesoporous silica nanoparticles for photothermal-controlled drug delivery in vivo. Angew Chem Int Ed. 2012;51(33):8373–8377. DOI:10.1002/anie.201203993
  • Wang D, Wu S. Red-light-responsive supramolecular valves for photocontrolled drug release from mesoporous nanoparticles. Langmuir. 2016;32(2):632–636.
  • Li M, Yan H, Teh C, et al. NIR-triggered drug release from switchable rotaxane-functionalized silica-covered Au nanorods. Chem Commun. 2014;50(68):9745–9748. DOI:10.1039/C4CC02966F
  • Cheng L, Jiang Y, Yan N, et al. Smart adsorbents with photoregulated molecular gates for both selective adsorption and efficient regeneration. ACS Appl Mater Interfaces. 2016;8(35):23404–23411. DOI:10.1021/acsami.6b07853
  • Zhang Z, Balogh D, Wang F, et al. Light-induced and redox-triggered uptake and release of substrates to and from mesoporous SiO2 nanoparticles. J Mater Chem B. 2013;1(25):3159. DOI:10.1039/c3tb20292e
  • Aznar E, Oroval M, Pascual L, et al. Gated materials for on-command release of guest molecules. Chem Rev. 2016;116(2):561–718. DOI:10.1021/acs.chemrev.5b00456
  • Wu MX, Yang YW. Metal-organic framework (MOF)-based drug/cargo delivery and cancer therapy. Adv Mater. 2017;29(23):1606134.
  • Nakata S, Miyaji T, Matsuda Y, et al. Mode switching of a self-propelled camphor disk sensitive to the photoisomerization of a molecular layer on water. Langmuir. 2014;30(25):7353–7357. DOI:10.1021/la5016803
  • Nakata S, Nasu K, Irie Y, et al. Self-propelled motion of a camphor disk on a photosensitive amphiphilic molecular layer. Langmuir. 2019;35(12):4233–4237. DOI:10.1021/acs.langmuir.8b04285
  • Matsuda Y, Suematsu NJ, Nakata S. Photo-sensitive self-motion of a BQ disk. Phys Chem Chem Phys. 2012;14:5988–5991.
  • Norikane Y, Tanaka S, Uchida E. Azobenzene crystals swim on water surface triggered by light. Cryst Eng Comm. 2016;18(38):7225–7228.
  • Yucknovsky A, Rich BB, Westfried A, et al. Self-propulsion of droplets via light-stimuli rapid control of their surface tension. Adv Mater Interfaces. 2021;8(22):2100751. DOI:10.1002/admi.202100751
  • Liu CW, Hsu CP, Yeh JA, et al. Light-actuated water droplet motions on ZnO nanorods. Microsyst Technol. 2013;19(2):245–251. DOI:10.1007/s00542-012-1562-5
  • Li W, Lei Y, Chen R, et al. Light-caused droplet bouncing from a cavity trap-assisted superhydrophobic surface. Langmuir. 2020;36(37):11068–11078. DOI:10.1021/acs.langmuir.0c02062
  • Wu Z, Lin X, Wu Y, et al. Near-infrared light-triggered “on/off” motion of polymer multilayer rockets. ACS Nano. 2014;8(6):6097–6105. DOI:10.1021/nn501407r
  • Xuan M, Wu Z, Shao J, et al. Near infrared light-powered Janus mesoporous silica nanoparticlemotors. J Am Chem Soc. 2016;138(20):6492–6497. DOI:10.1021/jacs.6b00902
  • Uda M, Kawashima H, Mayama H, et al. Locomotion of a nonaqueous liquid marble induced by near-infrared-light irradiation. Langmuir. 2021;37(14):4172–4182. DOI:10.1021/acs.langmuir.1c00041
  • Gao C, Wang L, Lin Y, et al. Droplets manipulated on photothermal organogel surfaces. Adv Funct Mater. 2018;28(35):1803072. DOI:10.1002/adfm.201803072
  • Dai B, Wang J, Xiong Z, et al. Programmable artificial phototactic microswimmer. Nat Nanotechnol. 2016;11(12):1087–1092. DOI:10.1038/nnano.2016.187
  • Wu S, Zhou L, Chen C, et al. Photothermal actuation of diverse liquids on an Fe3O4-doped slippery surface for electric switching and cell culture. Langmuir. 2019;35(43):13915–13922. DOI:10.1021/acs.langmuir.9b02068
  • Yilmaz M, Kuloglu HB, Erdogan H, et al. Light-driven unidirectional liquid motion on anisotropic gold nanorod arrays. Adv Mater Interfaces. 2015;2(12):1500226. DOI:10.1002/admi.201500226
  • Chen C, Mou F, Xu L, et al. Light-steered isotropic semiconductor micromotors. Adv Mater. 2017;29(3):1603374. DOI:10.1002/adma.201603374
  • Wu Y, Si T, Lin X, et al. Near infrared-modulated propulsion of catalytic janus polymer multilayer capsule motors. Chem Commun. 2015;51(3):511–514. DOI:10.1039/C4CC07182D
  • Geng H, Zhou K, Zhou J, et al. Sunlight-driven water transport via a reconfigurable pump. Angew Chem Int Ed. 2018;57(47):15435–15440. DOI:10.1002/anie.201808835
  • Ge F, Yang R, Tong X, et al. A multifunctional dye-doped liquid crystal polymer actuator: light-guided transportation, turning in locomotion, and autonomous motion. Angew Chem Int Ed. 2018;57(36):11758–11763. DOI:10.1002/anie.201807495
  • Lv X, Wang W, Yu H. A bioinspired photothermal pneumatic device enabling optical manipulation of microfluid toward precise control of microreactions. Adv Eng Mater. 2019;21(12):1900977.
  • Ren Y, Qi H, Chen Q, et al. Optofluidic control using light illuminated plasmonic nanostructure as microvalve. Int J Heat Mass Transf. 2019;133:1019–1025.
  • Yu Y, Nakano M, Ikeda T. Directed bending of a polymer film by light. Nature. 2003;425(6954):145.
  • Miyasaka H, Matsuda K, Abe J, et al. Photosynergetic responses in molecules and molecular aggregates. 1st ed. Miyasaka H, Matsuda K Abe J, editors. Singapore: Springer Singapore; 2020.
  • Tang X, Wang L. Loss-free photo-manipulation of droplets by pyroelectro-trapping on superhydrophobic surfaces. ACS Nano. 2018;12(9):8994–9004.
  • Li W, Tang X, Wang L. Photopyroelectric microfluidics. Sci Adv. 2020;6(38):1693.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.