533
Views
18
CrossRef citations to date
0
Altmetric
Article

Photoresponsive iodine-bonded liquid crystals based on azopyridine derivatives with a low phase-transition temperature

, , , , , , , , & show all
Pages 37-44 | Received 02 Dec 2017, Accepted 16 Apr 2018, Published online: 29 Apr 2018

References

  • Lehn JM. Perspectives in supramolecular chemistry-from molecular recognition towards molecular information processing and self-organization. Angew Chem Int Ed. 1990;29(11):1304–1319.
  • Paleos CM, Tsiourvas D. Supramolecular hydrogen-bonded liquid crystals. Liq Cryst. 2001;28(8):1127–1161.
  • Kato T, Mizoshita N, Kanie K. Hydrogen-bonded liquid crystalline materials: supramolecular polymeric assembly and the induction of dynamic function. Macromol Rapid Comm. 2001;22(11):797–814.
  • Lehn JM. Toward complex matter: supramolecular chemistry and self-organization. Proc Natl Acad Sci. 2002;99(8):4763–4768.
  • Kato T, Frechet JMJ. A new approach to mesophase stabilization through hydrogen bonding molecular interactions in binary mixtures. J Am Chem Soc. 1989;111(22):8533–8534.
  • Ichikawa T, Yoshio M, Hamasaki A, et al. Self-organization of room-temperature ionic liquids exhibiting liquid-crystalline bicontinuous cubic phases: formation of nano-ion channel networks. J Am Chem Soc. 2007;129(35):10662–10663.
  • Giroud-Godquin AM, Maitlis PM. Metallomesogens: metal complexes in organized fluid phases. Angew Chem Int Ed. 1991;30(4):375–402.
  • Metrangolo P, Resnati G, Pilati T, et al. Engineering functional materials by halogen bonding. J Polym Sci Pol Chem. 2007;45(1):1–15.
  • Cavallo G, Metrangolo P, Milani R, et al. The halogen bond. Chem Rev. 2016;116(4):2478–2601.
  • Bandara HMD, Burdette SC. Photoisomerization in different classes of azobenzene. Chem Soc Rev. 2012;41(5):1809–1825.
  • Chen Y, Yu H, Quan M, et al. Photothermal effect of azopyridine compounds and their applications. RSC Advances. 2015;5(6):4675–4680.
  • Chen Y, Quan M, Yu H, et al. Fabrication of nanofibres with azopyridine compounds in various acids and solvents. RSC Advances. 2015;5(39):31219–31225.
  • Zhang H, Hao R, Jackson JK, et al. Janus ultrathin film from multi-level self-assembly at air-water interfaces. Chem Commun. 2014;50(94):14843–14846.
  • Paterson DA, Xiang J, Singh G, et al. Reversible isothermal twist-bend nematic-nematic phase transition driven by the photoisomerization of an azobenzene-based nonsymmetric liquid crystal dimer. J Am Chem Soc. 2016;138(16):5283–5289.
  • Alaasar M, Poppe S, Dong Q, et al. Isothermal chirality switching with non-polarized light. Angew Chem. 2017;56(36):10801–10805.
  • Pan S, Ni M, Mu B, et al. Well-defined pillararene-based azobenzene liquid crystalline photoresponsive materials and their thin films with photomodulated surfaces. Adv Funct Mater. 2015;25(23):3571–3580.
  • Yu H. Recent advances in photoresponsive liquid-crystalline polymers containing azobenzene chromophores. J Mater Chem C. 2014;2(17):3047–3054.
  • Yu H. Photoresponsive liquid crystalline block copolymers: from photonics to nanotechnology. Prog Polym Sci. 2014;39(4):781–815.
  • Cui L, Zhao Y. Azopyridine side chain polymers: an efficient way to prepare photoactive liquid crystalline materials through self-assembly. Chem Mater. 2004;16(11):2076–2082.
  • Zhou H, Xue C, Weis P, et al. Photoswitching of glass transition temperatures of azobenzene-containing polymers induces reversible solid-to-liquid transitions. Nat Chem. 2017;9(2):145–151.
  • Bisoyi HK, Li Q. Light-driven liquid crystalline materials: from photo-induced phase transitions and property modulations to applications. Chem Rev. 2016;116(24):15089–15166.
  • Zhang X, Zhang J, Sun Y, et al. Erasable thin-film optical diode based on a photoresponsive liquid crystal polymer. Nanoscale. 2014;6(7):3854–3860.
  • Tan X, Li Z, Xia M, et al. Reversible photoresponsive chiral liquid crystal and multistimuli responsive organogels based on a cholesterol-azobenzene dimesogen. RSC Advances. 2016;6(24):20021–20026.
  • Nguyen HL, Horton PN, Hursthouse MB, et al. Halogen bonding: a new interaction for liquid crystal formation. J Am Chem Soc. 2004;126(1):16–17.
  • Metrangolo P, Präsang C, Resnati G, et al. Fluorinated liquid crystals formed by halogen bonding. Chem Commun. 2006;31(31):3290–3292.
  • Bruce DW, Metrangolo P, Meyer F, et al. Mesogenic, trimeric, halogen-bonded complexes from alkoxystilbazoles and 1,4-diiodotetrafluorobenzene. New J Chem. 2008;32(3):477–482.
  • Präsang C, Whitwood AC, Bruce DW. Spontaneous symmetry-breaking in halogen-bonded, bent-core liquid crystals: observation of a chemically driven Iso-N-N* phase sequence. Chem Commun. 2008;18:2137–2139.
  • Präsang C, Nguyen HL, Horton PN, et al. Trimeric liquid crystals assembled using both hydrogen and halogen bonding. Chem Commun. 2008;46:6164–6166.
  • McAllister LJ, Prasang C, Wong JPW, et al. Halogen-bonded liquid crystals of 4-alkoxystilbazoles with molecular iodine: a very short halogen bond and unusual mesophase stability. Chem Commun. 2013;49(38):3946–3948.
  • Bruce DW, Metrangolo P, Meyer F, et al. Structure-function relationships in liquid-crystalline halogen-bonded complexes. Chem Eur J. 2010;16(31):9511–9524.
  • 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):OP345–OP352.
  • Chen Y, Yu H, Zhang L, et al. Photoresponsive liquid crystals based on halogen bonding of azopyridines. Chem Commun. 2014;50(68):9647–9649.
  • Fernandez-Palacio F, Poutanen M, Saccone M, et al. Efficient light-induced phase transitions in halogen-bonded liquid crystals. Chem Mater. 2016;28(22):8314–8321.
  • Toh CL, Xu J, Lu X, et al. Synthesis and characterisation of main-chain hydrogen-bonded supramolecular liquid crystalline complexes formed by azo-containing compounds. Liq Cryst. 2008;35(3):241–251.
  • Xu J, Liu X, Ng JKP, et al. Trimeric supramolecular liquid crystals induced by halogen bonds. J Mater Chem. 2006;16(35):3540–3545.
  • González L, Gimeno N, Tejedor RM, et al. Halogen-bonding complexes based on bis (iodoethynyl) benzene units: a new versatile route to supramolecular materials. Chem Mater. 2013;25(22):4503–4510.
  • Desiraju GR, Ho PS, Kloo L, et al. Definition of the halogen bond (IUPAC Recommendations 2013). Pure Appl Chem. 2013;85(8):1711–1713.
  • Erdelyi M. Halogen bonding in solution. Chem Soc Rev. 2012;41(9):3547–3557.
  • Metrangolo P, Resnati G. Halogen bonding: a paradigm in supramolecular chemistry. Chem Eur J. 2001;7(12):2511–2519.
  • Yadav RA, Singh IS, The SO. Raman and infrared spectra and normal coordinate analysis for 1,2-diiodotetrafluorobenzene. J Raman Spectrosc. 1983;14(5):353–357.
  • Davy KJP, McMurtrie J, Rintoul L, et al. Vapour phase assembly of a halogen bonded complex of an isoindoline nitroxide and 1, 2-diiodotetrafluorobenzene. CrystEngComm. 2011;13(16):5062–5070.
  • De Santis A, Forni A, Liantonio R, et al. N...Br halogen bonding: one-dimensional infinite chains through the self-assembly of dibromotetrafluorobenzenes with dipyridyl derivatives. Chem Eur J. 2003;9(16):3974–3983.
  • Shen Q, Wei H, Zou W, et al. Cocrystals assembled by pyrene and 1,2- or 1,4-diiodotetrafluorobenzenes and their phosphorescent behaviors modulated by local molecular environment. CrystEngComm. 2012;14(3):1010–1015.
  • Imrie CT, Karasz FE, Attard GS. Comparison of the mesogenic properties of monomeric, dimeric, and side-chain polymeric liquid crystals. Macromolecules. 1993;26(3):545–550.
  • Xu Y, Qu W, Yang Q, et al. Synthesis and characterization of mesogen-jacketed liquid crystalline polymers through hydrogen-bonding. Macromolecules. 2015;45(6):2682–2689.
  • Ikeda T. Photomodulation of liquid crystal orientations for photonic applications. J Mater Chem. 2003;13(9):2037–2057.
  • Tian Y, Watanabe K, Kong X, et al. Synthesis, nanostructures, and functionality of amphiphilic liquid crystalline block copolymers with azobenzene moieties. Macromolecules. 2002;35(9):3739–3747.
  • Rahman ML, Sarkar SM, Yusoff MM, et al. Synthesis of new U-shaped azobenzene liquid crystals for photoswitching properties. RSC Advances. 2015;5(106):87019–87029.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.