Photo-responsive polysiloxane-based azobenzene liquid crystalline polymers prepared by thiol-ene click chemistry

References

• Beharry AA, Woolley GA. Azobenzene photoswitches for biomolecules. Iryo Yakugaku. 2011;40:4422–4437.
   Google Scholar
• Kumar GS, Neckers DC. Photochemistry of azobenzene-containing polymers. Chem Rev. 1989;89:1915–1925. doi:10.1021/cr00098a012.
   Web of Science ®Google Scholar
• Bandara HM, Burdette SC. Photoisomerization in different classes of azobenzene. Lect Notes Phys. 2012;41:1809–1825.
   Google Scholar
• Rabek JF. Photochemistry and photophysics. Boca Raton (FL): CRC Press; 1990.
   Google Scholar
• White TJ, Tabiryan NV, Serak SV, et al. A high frequency photodriven polymer oscillator. Soft Matter. 2008;4:1796–1798. doi:10.1039/b805434g.
   Web of Science ®Google Scholar
• Li MH, Keller P. Artificial muscles based on liquid crystal elastomers. Philos Trans R Soc A. 2006;364:2763–2777. doi:10.1098/rsta.2006.1853.
   Web of Science ®Google Scholar
• Li M-H, Keller P, Li B, et al. Light-driven side-on nematic elastomer actuators. Adv Mater. 2003;15:569–572. doi:10.1002/adma.200304552.
   Web of Science ®Google Scholar
• Verploegen E, Soulages J, Kozberg M, et al. Reversible switching of the shear modulus of photoresponsive liquid-crystalline polymers. Angew Chem Int Ed. 2009;48:3494–3498. doi:10.1002/anie.200900583.
   PubMed Web of Science ®Google Scholar
• Guo Q, Srivastava AK, Chigrinov VG, et al. Polymer and azo-dye composite: a photo-alignment layer for liquid crystals. Liq Cryst. 2014;41:1465–1472. doi:10.1080/02678292.2014.926404.
   Web of Science ®Google Scholar
• Xie H, Wang L, Wang H, et al. Electrically tunable properties of wideband-absorptive and reflection-selective films based on multi-dichroic dye-doped cholesteric liquid crystals. Liq Cryst. 2015;42:1698–1705. doi:10.1080/02678292.2015.1055600.
   Web of Science ®Google Scholar
• Ichimura K. Photoalignment of liquid-crystal systems. Chem Rev. 2000;100:1847–1874. doi:10.1021/cr980079e.
   PubMed Web of Science ®Google Scholar
• Natansohn A, Rochon P. Photoinduced motions in azo-containing polymers. Chem Rev. 2002;102:4139–4176. doi:10.1021/cr970155y.
   PubMed Web of Science ®Google Scholar
• Warner M, Terentjev E. Liquid crystal elastomers. Oxford: Oxford University Press; 2003.
   Google Scholar
• Barrett CJ, Mamiya J, Yager KG, et al. Photo-mechanical effects in azobenzene-containing soft materials. Soft Matter. 2007;3:1249–1261. doi:10.1039/b705619b.
   PubMed Web of Science ®Google Scholar
• Wu W, Yao L, Yang T, et al. NIR-light-induced deformation of cross-linked liquid-crystal polymers using upconversion nanophosphors. J Am Chem Soc. 2011;133:15810–15813. doi:10.1021/ja2043276.
   PubMed Web of Science ®Google Scholar
• Jiang Z, Xu M, Li F, et al. Red-light-controllable liquid-crystal soft actuators via low-power excited upconversion based on triplet-triplet annihilation. J Am Chem Soc. 2013;135:16446–16453. doi:10.1021/ja406020r.
   PubMed Web of Science ®Google Scholar
• Deng W, Albouy P-A, Lacaze E, et al. Azobenzene-containing liquid crystal triblock copolymers: synthesis, characterization, and self-assembly behavior. Macromolecules. 2008;41:2459–2466. doi:10.1021/ma702590j.
   Web of Science ®Google Scholar
• Zhu Y, Wang X. Synthesis and photoresponsive properties of two liquid crystalline polymers bearing branched azobenzene-containing side chains. Polym Chem. 2013;4:5108–5118. doi:10.1039/c3py00757j.
   Web of Science ®Google Scholar
• Wei R, Xu Z, Liu X, et al. Liquid-crystalline compounds containing both a strong push–pull azo chromophore and a cholesteryl unit as photoresponsive molecular glass materials. J Mater Chem C. 2015;3:10925–10933. doi:10.1039/C5TC02126J.
   Web of Science ®Google Scholar
• Shi Z, Shu X, Chen D. Rationally designed syntheses and self-organized superstructure investigations of liquid crystalline dendrimers. Prog Chem. 2009;21:1534–1545.
   Web of Science ®Google Scholar
• 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;25:3571–3580. doi:10.1002/adfm.201500942.
   Web of Science ®Google Scholar
• Duan J, Wang M, Bian H, et al. Azobenzene mesogen-passivated gold nanoparticles: controlled preparation, self-organized superstructures, thermal behavior and photoisomerization. Mater Chem Phys. 2014;148:1013–1021. doi:10.1016/j.matchemphys.2014.09.012.
   Web of Science ®Google Scholar
• Imam MR, Peterca M, Edlund U, et al. Dendronized supramolecular polymers self-assembled from dendritic ionic liquids. J Polym Sci Part A Polym Chem. 2009;47:4165–4193. doi:10.1002/pola.23523.
   Web of Science ®Google Scholar
• Rodriguez-Parada JM, Percec V. Poly(vinyl ether)s and poly(propenyl ether)s containing mesogenic groups: A new class of side-chain liquid-crystalline polymers. J Polym Sci Part A Polym Chem. 2003;24:1363–1378. doi:10.1002/pola.1986.080240619.
   Web of Science ®Google Scholar
• Cong C, Liu JC, Fang S, et al. Tuning surface microstructure and gradient property of polymer by photopolymerizable polysiloxane-modified nanogels. RSC Adv. 2014;4:28928–28936. doi:10.1039/C4RA02176B.
   PubMed Web of Science ®Google Scholar
• Declue MS, Siegel JS. Polysiloxane-bound ligand accelerated catalysis: a modular approach to heterogeneous and homogeneous macromolecular asymmetric dihydroxylation ligands. Org Biomol Chem. 2005;36:2287–2298.
   Google Scholar
• Jadhav SA. Surface modification of iron oxide (Fe2O3) pigment particles with amino-functional polysiloxane for improved dispersion stability and hydrophobicity. Pigm Resin Technol. 2014;43:219–227. doi:10.1108/PRT-07-2013-0057.
   Web of Science ®Google Scholar
• Finkelmann H, Nishikawa E, Pereira GG, et al. A new opto-mechanical effect in solids. Phys Rev Lett. 2001;87:015501. doi:10.1103/PhysRevLett.87.015501.
   PubMed Web of Science ®Google Scholar
• Cviklinski J, Tajbakhsh AR, Terentjev EM. UV isomerisation in nematic elastomers as a route to photo-mechanical transducer. Euro Phys J E. 2002;9:427–434. doi:10.1140/epje/i2002-10095-y.
   PubMed Web of Science ®Google Scholar
• Ohm C, Brehmer M, Zentel R. Liquid crystalline elastomers as actuators and sensors. Adv Mater. 2010;22:3366–3387. doi:10.1002/adma.200904059.
   PubMed Web of Science ®Google Scholar
• Petr M, Hammond PT. Room temperature rapid photoresponsive azobenzene side chain liquid crystal polymer. Macromolecules. 2011;44:8880–8885. doi:10.1021/ma2013173.
   Web of Science ®Google Scholar
• Petr M, Katzman B, Dinatale W, et al. Synthesis of a new, low-Tg siloxane thermoplastic elastomer with a functionalizable backbone and its use as a rapid, room temperature photoactuator. Macromolecules. 2013;46:2823–2832. doi:10.1021/ma400031z.
   Web of Science ®Google Scholar
• Wang M, Sayed SM, Guo L-X, et al. Multi-stimuli responsive carbon nanotube incorporated polysiloxane azobenzene liquid crystalline elastomer composites. Macromolecules. 2016;49:663–671. doi:10.1021/acs.macromol.5b02388.
   Web of Science ®Google Scholar
• Mukbaniani O, Titvinidze G, Tatrishvili T, et al. Formation of polymethylsiloxanes with alkyl side groups. J Appl Polym Sci. 2007;104:1176–1183. doi:10.1002/(ISSN)1097-4628.
   Web of Science ®Google Scholar
• Kade MJ, Burke DJ, Hawker CJ. The power of thiol-ene chemistry. J Polym Sci Part A Polym Chem. 2010;48:743–750. doi:10.1002/pola.23824.
   Web of Science ®Google Scholar
• Campos LM, Meinel I, Guino RG, et al. Highly versatile and robust materials for soft imprint lithography based on thio-ene click chemistry. Adv Mater. 2008;20:3728–3733. doi:10.1002/adma.200800330.
   Web of Science ®Google Scholar
• Campos LM, Truong TT, Shim DE, et al. Applications of photocurable PMMS thiol−ene stamps in soft lithography. Chem Mater. 2009;21:5319–5326. doi:10.1021/cm902506a.
   Web of Science ®Google Scholar
• Yang H, Zhang Q, Lin B, et al. Thermo-sensitive electrospun fibers prepared by a sequential thiol-ene click chemistry approach. J Polym Sci Part A Polym Chem. 2012;50:4182–4190. doi:10.1002/pola.26244.
   Web of Science ®Google Scholar
• Yang H, Liu JJ, Wang ZF, et al. Near-infrared-responsive gold nanorod/liquid crystalline elastomer composites prepared by sequential thiol-click chemistry. Chem Commum. 2015;51:12126–12129. doi:10.1039/C5CC02599K.
   PubMed Web of Science ®Google Scholar
• Yang H, Liu M-X, Yao Y-W, et al. Polysiloxane-based liquid crystalline polymers and elastomers prepared by thiol–ene chemistry. Macromolecules. 2013;46:3406–3416. doi:10.1021/ma400462e.
   Web of Science ®Google Scholar
• Yang H. Organocatalysis in polysiloxane gels: a magnetic-stir-bar encapsulated catalyst system prepared by thiol–ene photo-click immobilization. RSC Adv. 2015;5:7304–7310. doi:10.1039/C4RA16351F.
   Web of Science ®Google Scholar
• Li M, Auroy P, Keller P. An azobenzene-containing side-on liquid crystal polymer. Liq Cryst. 2000;27:1497–1502. doi:10.1080/026782900750018663.
   Web of Science ®Google Scholar
• Jaffe HH, Orchin M. Ultraviolet spectroscopy. (Book reviews: theory and applications of ultraviolet spectroscopy). Science. 1963;139:497–525.
   PubMed Web of Science ®Google Scholar
• Bobrovsky A, Boiko N, Shibaev V, et al. Photo-orientation phenomena in photosensitive chiral nematic copolymers. Liq Cryst. 2002;29:1469–1476. doi:10.1080/02678290260372664.
   Web of Science ®Google Scholar
• Ikeda T, Horiuchi S, Karanjit DB, et al. Photochemically induced isothermal phase transition in polymer liquid crystals with mesogenic phenyl benzoate side chains. 1. Calorimetric studies and order parameters. Macromolecules. 1990;23:42–48. doi:10.1021/ma00203a009.
   Web of Science ®Google Scholar
• Kurihara S, Sakamoto A, Yoneyama D, et al. Photochemical switching behavior of liquid crystalline polymer networks containing azobenzene molecules. Macromolecules. 1999;32:6493–6498. doi:10.1021/ma990231u.
   Web of Science ®Google Scholar
• Nabeshima Y, Shishido A, Kanazawa A, et al. Synthesis of novel liquid-crystalline thiophene derivatives and evaluation of their photoresponsive behavior. Chem Mater. 1997;9:1480–1487. doi:10.1021/cm970082z.
   Web of Science ®Google Scholar
• Tsutsumi O, Shiono T, Ikeda TA, et al. Photochemical phase transition behavior of nematic liquid crystals with azobenzene moieties as both mesogens and photosensitive chromophores. J Phys Chem B. 1997;101:1332–1337. doi:10.1021/jp961565d.
   Web of Science ®Google Scholar
• Bronnikov S, Cozan V, Nasonov A. Kinetics of the phase transition in an isotropic liquid crystalline dimer subjected to a deep temperature quench. Phase Transit. 2007;80:831–839. doi:10.1080/01411590701325111.
   Web of Science ®Google Scholar
• Bronnikov S, Dierking I. Quench depth dependence of liquid crystal nucleus growth: A time resolved statistical analysis. Physica B Condens Matter. 2005;358:339–347. doi:10.1016/j.physb.2005.01.470.
   Web of Science ®Google Scholar
• Bronnikov S, Racles C, Nasonov A, et al. Kinetics of the nematic ordered phase growth during a temperature quench of an isotropic siloxane-azomethine polymer. Liq Cryst. 2006;33:1015–1019. doi:10.1080/02678290600930964.
   Web of Science ®Google Scholar
• Dierking I. Universal growth laws in liquid crystals far from equilibrium. Appl Phys A Mater Sci Process. 2001;72:307–310. doi:10.1007/s003390100732.
   Web of Science ®Google Scholar
• Mita I, Horie K, Hirao K. Photochemistry in polymer solids. 9. Photoisomerization of azobenzene in a polycarbonate film. Macromolecules. 1989;22:558–563. doi:10.1021/ma00192a008.
   Web of Science ®Google Scholar
• Niezgoda I, Jaworska J, Pociecha D, et al. The kinetics of the E-Z-E isomerisation and liquid-crystalline properties of selected azobenzene derivatives investigated by the prism of the ester group inversion. Liq Cryst. 2015;42:1148–1158. doi:10.1080/02678292.2015.1031198.
   Web of Science ®Google Scholar
• Imrie CT, Karasz FE, Attard GS. The effect of molecular weight on the thermal properties of polystyrene-based sidechain liquid-crystalline polymers. J Macromol Sci Pure Appl Chem. 1994;31:1221–1232. doi:10.1080/10601329409351547.
   Web of Science ®Google Scholar