Construction of Supramolecular Chirality in Polymer Systems: Chiral Induction, Transfer and Application

Xiao-Xiao Cheng; Teng-Fei Miao; Lu Yin; Wei Zhang; Xiu-Lin Zhu

doi:10.1007/s10118-021-2561-8

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Construction of Supramolecular Chirality in Polymer Systems: Chiral Induction, Transfer and Application

FEATURE ARTICLE | Updated：2021-05-31

- Construction of Supramolecular Chirality in Polymer Systems: Chiral Induction, Transfer and Application
- Chinese Journal of Polymer Science Vol. 39, Issue 11, Pages: 1357-1375(2021)
- Affiliations：
  
  a.State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
  b.State Key Laboratory of Radiation Medicine and Protection, Soochow University, Suzhou 215123, China
- Author bio：
  
  weizhang@suda.edu.cn
- Funds：
- DOI：10.1007/s10118-021-2561-8
  CLC：
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Xiao-Xiao Cheng, Teng-Fei Miao, Lu Yin, et al. Construction of Supramolecular Chirality in Polymer Systems: Chiral Induction, Transfer and Application. [J]. Chinese Journal of Polymer Science 39(11):1357-1375(2021)
DOI：

Xiao-Xiao Cheng, Teng-Fei Miao, Lu Yin, et al. Construction of Supramolecular Chirality in Polymer Systems: Chiral Induction, Transfer and Application. [J]. Chinese Journal of Polymer Science 39(11):1357-1375(2021) DOI： 10.1007/s10118-021-2561-8.

摘要

Abstract

Chirality, commonly found in organisms, biomolecules and nature such as ,L,-amino acids and ,D,-sugars, has been extensively studied in chemistry and biomedical science. Hence, the demand for simple and efficient construction of chiral structures, especially chiral polymers, has been rapidly growing due to their potential applications in chemosensors, asymmetric catalysis and biological materials. However, most chiral polymers reported are prepared directly from chiral monomers/chiral catalysts, the corresponding strategies usually involve tedious and expensive design and synthesis. Fortunately, chirality induction strategies (such as circularly polarized light, chiral solvation and chiral gelation ,etc,.) have been known to be highly versatile and efficient in producing chirality from achiral polymers. In this feature article, the current research on chirality induction, transfer and application in achiral polymer systems is summarized. Furthermore, this article discusses some basic concepts, seminal studies, recent advances, the structural design principles, as well as perspectives in the construction and applications of chiral polymers derived from achiral monomers, with the hope to attract more interest from researchers and further advance the development of chiral chemistry.

关键词

Keywords

ChiralityChirality inductionAchiral polymerSupramolecular chemistrySelf-assembly

references

Yashima, E.; Maeda, K.; Iida, H.; Furusho, Y.; Nagai, K. . Helical polymers: Synthesis, structures, and functions . Chem. Rev. , 2009 . 109 6102 -6211 . DOI:10.1021/cr900162qhttp://doi.org/10.1021/cr900162q .

Cheng, X. X.; Miao, T. F.; Qian, Y. L.; Zhang, Z. B.; Zhang, W.; Zhu, X. L. . Supramolecular chirality in azobenzene-containing polymer system: traditional postpolymerization self-assembly versus in situ supramolecular self-assembly strategy . Int. J. Mol. Sci. , 2020 . 21 6186 DOI:10.3390/ijms21176186http://doi.org/10.3390/ijms21176186 .

Gal, J. . Pasteur and the art of chirality . Nat. Chem. , 2017 . 9 604 -605 . DOI:10.1038/nchem.2790http://doi.org/10.1038/nchem.2790 .

Hembury, G. A.; Borovkov, V. V.; Inoue, Y. . Chirality-sensing supramolecular systems . Chem. Rev. , 2008 . 108 1 -73 . DOI:10.1021/cr050005khttp://doi.org/10.1021/cr050005k .

Yashima, E.; Maeda, K. . Chirality-responsive helical polymers . Macromolecules , 2008 . 41 3 -12 . DOI:10.1021/ma071453shttp://doi.org/10.1021/ma071453s .

Liu, M. H.; Zhang, L.; Wang, T. Y. . Supramolecular chirality in self-assembled systems . Chem. Rev. , 2015 . 115 7304 -7397 . DOI:10.1021/cr500671phttp://doi.org/10.1021/cr500671p .

Chen, X. L.; Kang, Y.; Zeng, S. . Analysis of stereoisomers of chiral drug by mass spectrometry . Chirality , 2018 . 30 609 -618 . DOI:10.1002/chir.22833http://doi.org/10.1002/chir.22833 .

Xing, P. Y.; Zhao, Y. L. . Controlling supramolecular chirality in multicomponent self-assembled systems . Acc. Chem. Res. , 2018 . 51 2324 -2334 . DOI:10.1021/acs.accounts.8b00312http://doi.org/10.1021/acs.accounts.8b00312 .

Wang, J.; Li, C. Y.; Jin, S.; Weng, X.; Van Horn, R. M.; Graham, M. J.; Zhang, W. B.; Jeong, K. U.; Harris, F. W.; Lotz, B.; Cheng, S. Z. D. . Helical crystal assemblies in nonracemic chiral liquid crystalline polymers: where chemistry and physics meet . Ind. Eng. Chem. Res. , 2010 . 49 11936 -11947 . DOI:10.1021/ie100248rhttp://doi.org/10.1021/ie100248r .

Mateos-Timoneda, M. A.; Crego-Calama, M.; Reinhoudt, D. N. . Supramolecular chirality of self-assembled systems in solution . Chem. Soc. Rev. , 2004 . 33 363 -372 . DOI:10.1039/b305550ghttp://doi.org/10.1039/b305550g .

Zhang, W.; Ochi, K.; Fujiki, M.; Naito, M.; Ishikawa, M.; Kaneto, K.; Takashima, W.; Saeki, A.; Seki, S. . Programmed high-hole-mobility supramolecular polymers from disk-shaped molecules . Adv. Funct. Mater. , 2010 . 20 3941 -3947 . DOI:10.1002/adfm.201001072http://doi.org/10.1002/adfm.201001072 .

Watanabe, K.; Iida, H.; Akagi, K. . Circularly polarized blue luminescent spherulites consisting of hierarchically assembled Ionic conjugated polymers with a helically π-stacked structure . Adv. Mater. , 2012 . 24 6451 -6456 . DOI:10.1002/adma.201203155http://doi.org/10.1002/adma.201203155 .

Moriuchi, T.; Nishiyama, M.; Yoshida, K.; Ishikawa, T.; Hirao, T. . Chiral helicity induced by hydrogen bonding and chirality of podand histidyl moieties . Org. Lett. , 2001 . 3 1459 -1461 . DOI:10.1021/ol0100327http://doi.org/10.1021/ol0100327 .

Marinelli, F.; Sorrenti, A.; Corvaglia, V.; Leone, V.; Mancini, G. . Molecular description of the propagation of chirality from molecules to complex systems: different mechanisms controlled by hydrophobic interactions . Chem. Eur. J. , 2012 . 18 14680 -14688 . DOI:10.1002/chem.201202342http://doi.org/10.1002/chem.201202342 .

Bai, S.; Debnath, S.; Javid, N.; Frederix, P. W. J. M.; Fleming, S.; Pappas, C.; Ulijn, R. V. . Differential self-assembly and tunable emission of aromatic peptide bola-amphiphiles containing perylene bisimide in polar solvents including water . Langmuir , 2014 . 30 7576 -7584 . DOI:10.1021/la501335ehttp://doi.org/10.1021/la501335e .

Yue, B. B.; Zhu, L. L. . Dynamic modulation of supramolecular chirality driven by factors from internal to external levels . Chem. Asian J. , 2019 . 14 2172 -2180 . DOI:10.1002/asia.201900460http://doi.org/10.1002/asia.201900460 .

Wang, S.; Feng, X. Y.; Zhang, J.; Yu, P.; Guo, Z. X.; Li, Z. B.; Wan, X. H. . Helical conformations of poly(3,5-disubstituted phenylacetylene)s tuned by pendant structure and solvent . Macromolecules , 2017 . 50 3489 -3499 . DOI:10.1021/acs.macromol.7b00615http://doi.org/10.1021/acs.macromol.7b00615 .

Van den Bergh, K.; Cosemans, I.; Verbiest, T.; Koeckelberghs, G. . Expression of supramolecular chirality in block copoly(thiophene)s . Macromolecules , 2010 . 43 3794 -3800 . DOI:10.1021/ma100266bhttp://doi.org/10.1021/ma100266b .

Nagata, Y.; Yamada, T.; Adachi, T.; Akai, Y.; Yamamoto, T.; Suginome, M. . Solvent-dependent switch of helical main-chain chirality in sergeants-and-soldiers-type poly(quinoxaline-2,3-diyl)s: effect of the position and structures of the "sergeant" chiral units on the screw-sense induction . J. Am. Chem. Soc. , 2013 . 135 10104 -10113 . DOI:10.1021/ja403391mhttp://doi.org/10.1021/ja403391m .

Tejedor, R. M.; Oriol, L.; Serrano, J. L.; Urena, F. P.; Gonzalez, J. J. L. . Photoinduced chiral nematic organization in an achiral glassy nematic azopolymer . Adv. Funct. Mater. , 2007 . 17 3486 -3492 . DOI:10.1002/adfm.200700202http://doi.org/10.1002/adfm.200700202 .

Huang, S.; Chen, Y. X.; Ma, S. D.; Yu, H. F. . Hierarchical self-assembly in liquid-crystalline block copolymers enabled by chirality transfer . Angew. Chem. Int. Ed. , 2018 . 57 12524 -12528 . DOI:10.1002/anie.201807379http://doi.org/10.1002/anie.201807379 .

Akagi, K. . Helical polyacetylene: asymmetric polymerization in a chiral liquid-crystal field . Chem. Rev. , 2009 . 109 5354 -5401 . DOI:10.1021/cr900198khttp://doi.org/10.1021/cr900198k .

Haraguchi, S.; Numata, M.; Li, C.; Nakano, Y.; Fujiki, M.; Shinkai, S. . Circularly polarized luminescence from supramolecular chiral complexes of achiral conjugated polymers and a neutral polysaccharide . Chem. Lett. , 2009 . 38 254 -255 . DOI:10.1246/cl.2009.254http://doi.org/10.1246/cl.2009.254 .

Yashima, E.; Matsushima, T.; Okamoto, Y. . Poly((4-carboxyphenyl)acetylene) as a probe for chirality assignment of amines by circular-dichroism . J. Am. Chem. Soc. , 1995 . 117 11596 -11597 . DOI:10.1021/ja00151a032http://doi.org/10.1021/ja00151a032 .

Nakashima, H.; Koe, J. R.; Torimitsu, K.; Fujiki, M. . Transfer and amplification of chiral molecular information to polysilylene aggregates . J. Am. Chem. Soc. , 2001 . 123 4847 -4848 . DOI:10.1021/ja010119nhttp://doi.org/10.1021/ja010119n .

Kaneko, T.; Liang, X. Y.; Kawami, A.; Sato, M.; Namikoshi, T.; Teraguchi, M.; Aoki, T. . Transformation from preformed racemic helical poly(phenylacetylene)s to the enantioenriched helical polymers by chiral solvation, followed by removal of the chiral solvents . Polym. J. , 2012 . 44 327 -333 . DOI:10.1038/pj.2011.144http://doi.org/10.1038/pj.2011.144 .

Yan, Y.; Yu, Z.; Huang, Y. W.; Yuan, W. X.; Wei, Z. X. . Helical polyaniline nanofibers induced by chiral dopants by a polymerization process . Adv. Mater. , 2007 . 19 3353 -3357 . DOI:10.1002/adma.200700846http://doi.org/10.1002/adma.200700846 .

Maeda, K.; Mochizuki, H.; Osato, K.; Yashima, E. . Stimuli-responsive helical poly(phenylacetylene)s bearing cyclodextrin pendants that exhibit enantioselective gelation in response to chirality of a chiral amine and hierarchical super-structured helix formation . Macromolecules , 2011 . 44 3217 -3226 . DOI:10.1021/ma200537phttp://doi.org/10.1021/ma200537p .

Wang, Y.; Sakamoto, T.; Nakano, T. . Molecular chirality induction to an achiral π-conjugated polymer by circularly polarized light . Chem. Commun. , 2012 . 48 1871 -1873 . DOI:10.1039/c2cc17027bhttp://doi.org/10.1039/c2cc17027b .

Green, M. M.; Park, J. W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. . The macromolecular route to chiral amplification . Angew. Chem. Int. Ed. , 1999 . 38 3139 -3154. .

Dellaportas, P.; Jones, R. G.; Holder, S. J. . Induction of preferential helical screw senses in optically inactive polysilanes via chiral solvation . Macromol. Rapid Commun. , 2002 . 23 99 -103 . DOI:10.1002/1521-3927(20020101)23:2<99::AID-MARC99>3.0.CO;2-Mhttp://doi.org/10.1002/1521-3927(20020101)23:2<99::AID-MARC99>3.0.CO;2-M .

Nakano, Y.; Liu, Y.; Fujiki, M. . Ambidextrous circular dichroism and circularly polarised luminescence from poly(9,9-di-n-decylfluorene) by terpene chirality transfer . Polym. Chem. , 2010 . 1 460 -469 . DOI:10.1039/B9PY00288Jhttp://doi.org/10.1039/B9PY00288J .

Kim, H.; Jin, Y. J.; Kim, B. S. I.; Aoki, T.; Kwak, G. . Optically active conjugated polymer nanoparticles from chiral solvent annealing and nanoprecipitation . Macromolecules , 2015 . 48 4754 -4757 . DOI:10.1021/acs.macromol.5b01034http://doi.org/10.1021/acs.macromol.5b01034 .

Green, M. M.; Khatri, C.; Peterson, N. C. . A macromolecular conformational change driven by a minute chiral solvation energy . J. Am. Chem. Soc. , 1993 . 115 4941 -4942 . DOI:10.1021/ja00064a086http://doi.org/10.1021/ja00064a086 .

Lee, D.; Jin, Y. J.; Kim, H.; Suzuki, N.; Fujiki, M.; Sakaguchi, T.; Kim, S. K.; Lee, W. E.; Kwak, G. . Solvent-to-polymer chirality transfer in intramolecular stack structure . Macromolecules , 2012 . 45 5379 -5386 . DOI:10.1021/ma300976rhttp://doi.org/10.1021/ma300976r .

Fujiki, M.; Jalilah, A.; Suzuki, N.; Taguchi, M.; Zhang, W.; Abdellatif, M. M.; Nomura, K. . Chiral optofluidics: gigantic circularly polarized light enhancement of all-trans-poly(9,9-di-n-octylfluorene-2,7-vinylene) during mirror-symmetry-breaking aggregation by optically tuning fluidic media . RSC Adv. , 2012 . 2 6663 -6671 . DOI:10.1039/c2ra20430dhttp://doi.org/10.1039/c2ra20430d .

Fujiki, M.; Kawagoe, Y.; Nakano, Y.; Nakao, A. . Mirror-symmetry-breaking in poly[(9,9-di-n-octylfluorenyl-2,7-diyl)-alt-biphenyl] (PF8P2) is susceptible to terpene chirality, achiral solvents, and mechanical stirring . Molecules , 2013 . 18 7035 -7057 . DOI:10.3390/molecules18067035http://doi.org/10.3390/molecules18067035 .

Nakano, Y.; Ichiyanagi, F.; Naito, M.; Yang, Y. G.; Fujiki, M. . Chiroptical generation and inversion during the mirror-symmetry-breaking aggregation of dialkylpolysilanes due to limonene chirality . Chem. Commun. , 2012 . 48 6636 -6638 . DOI:10.1039/c2cc17845ahttp://doi.org/10.1039/c2cc17845a .

Kawagoe, Y.; Fujiki, M.; Nakano, Y. . Limonene magic: Noncovalent molecular chirality transfer leading to ambidextrous circularly polarised luminescent π-conjugated polymers . New J. Chem. , 2010 . 34 637 -647 . DOI:10.1039/b9nj00733dhttp://doi.org/10.1039/b9nj00733d .

Yu, H. T.; Tang, J. W.; Feng, Y. Y.; Feng, W. . Structural design and application of azo-based supramolecular polymer systems . Chinese J. Polym. Sci. , 2019 . 37 1183 -1199 . DOI:10.1007/s10118-019-2331-zhttp://doi.org/10.1007/s10118-019-2331-z .

Yu, C. Y.; Mu, J. H.; Fu, Y. L.; Zhang, Y. C.; Han, J. S.; Zhao, R. Y.; Zhao, J.; Wang, Z. H.; Zhao, Z. C.; Li, W. J.; Liu, F. S. . Azobenzene based photo-responsive mechanical actuator fabricated by intermolecular H-bond interaction . Chinese J. Polym. Sci. , 2021 . 39 417 -424 . DOI:10.1007/s10118-021-2504-4http://doi.org/10.1007/s10118-021-2504-4 .

Liang, S. F.; Nie, C.; Yan, J.; Zhang, Q. J.; Wu, S. . Photoinduced reversible solid-to-liquid transitions and directional photofluidization of azobenzene-containing polymers . Chinese J. Polym. Sci. , 2020 . DOI:10.1007/s10118-021-2519-xhttp://doi.org/10.1007/s10118-021-2519-x .

Wang, L. B.; Pan, X. Q.; Zhao, Y.; Chen, Y.; Zhang, W.; Tu, Y. F.; Zhang, Z. B.; Zhu, J.; Zhou, N. C.; Zhu, X. L. . A straightforward protocol for the highly efficient preparation of main-chain azo polymers directly from bisnitroaromatic compounds by the photocatalytic process . Macromolecules , 2015 . 48 1289 -1295 . DOI:10.1021/acs.macromol.5b00048http://doi.org/10.1021/acs.macromol.5b00048 .

Wang, K.; Yin, L.; Miu, T. F.; Liu, M.; Zhao, Y.; Chen, Y.; Zhou, N. C.; Zhang, W.; Zhu, X. L. . Design and synthesis of a novel azobenzene-containing polymer both in the main- and side-chain toward unique photocontrolled isomerization properties . Mater. Chem. Front. , 2018 . 2 1112 -1118 . DOI:10.1039/C8QM00035Bhttp://doi.org/10.1039/C8QM00035B .

Zhang, W.; Yoshida, K.; Fujiki, M.; Zhu, X. L. . Unpolarized-light-driven amplified chiroptical modulation between chiral aggregation and achiral disaggregation of an azobenzene-alt-fluorene copolymer in limonene . Macromolecules , 2011 . 44 5105 -5111 . DOI:10.1021/ma2012128http://doi.org/10.1021/ma2012128 .

Zhang, S. S.; Liu, J. F.; Zhang, J.; Wang, L. B.; Zhang, W.; Zhu, X. L. . Preparation of chiral and fluorescent nanoparticles of hyperbranched conjugated polymers by the solvent chirality transfer technology . Acta Polymerica Sinica (in Chinese) , 2013 . 426 -435. .

Liu, J. F.; Zhang, J.; Zhang, S. S.; Suzuki, N.; Fujiki, M.; Wang, L. B.; Li, L.; Zhang, W.; Zhou, N. C.; Zhu, X. L. . Chiroptical generation and amplification of hyperbranched π-conjugated polymers in aggregation states driven by limonene chirality . Polym. Chem. , 2014 . 5 784 -791 . DOI:10.1039/C3PY01037Fhttp://doi.org/10.1039/C3PY01037F .

Wang, L. B.; Suzuki, N.; Liu, J. F.; Matsuda, T.; Rahim, N. A. A.; Zhang, W.; Fujiki, M.; Zhang, Z. B.; Zhou, N. C.; Zhu, X. L. . Limonene induced chiroptical generation and inversion during aggregation of achiral polyfluorene analogs: structure-dependence and mechanism . Polym. Chem. , 2014 . 5 5920 -5927 . DOI:10.1039/C4PY00865Khttp://doi.org/10.1039/C4PY00865K .

Zhao, Y.; Rahirn, N. A. A.; Xia, Y. J.; Fujiki, M.; Song, B.; Zhang, Z. B.; Zhang, W.; Zhu, X. L. . Supramolecular chirality in achiral polyfluorene: chiral gelation, memory of chirality, and chiral sensing property . Macromolecules , 2016 . 49 3214 -3221 . DOI:10.1021/acs.macromol.6b00376http://doi.org/10.1021/acs.macromol.6b00376 .

Zhao, Y.; Yin, L.; Liu, J. J.; Chen, H. L.; Zhang, W. . Helical screw sense bias in chiral polyfluorene stimulated by solvent . Chirality , 2017 . 29 107 -114 . DOI:10.1002/chir.22677http://doi.org/10.1002/chir.22677 .

Liu, J. J.; Zhao, Y.; Chen, H. L.; Zhang, Z. B.; Zhang, W.; Zhu, X. L. . Rapid limonene-induced mirror symmetry breaking in achiral polyfluorene containing pendant crown ether groups: enhanced by ion complexation . React. Funct. Polym. , 2017 . 121 76 -81 . DOI:10.1016/j.reactfunctpolym.2017.10.014http://doi.org/10.1016/j.reactfunctpolym.2017.10.014 .

Zhao, Y.; Chen, H. L.; Yin, L.; Cheng, X. X.; Zhang, W.; Zhu, X. L. . Chirality induction of achiral polydialkylfluorenes by chiral solvation: odd-even and side chain length dependence . Polym. Chem. , 2018 . 9 2295 -2301 . DOI:10.1039/C8PY00114Fhttp://doi.org/10.1039/C8PY00114F .

Li, S.; Miao, T. F.; Cheng, X. X.; Zhao, Y.; Zhang, W.; Zhu, X. L. . Different phase-dominated chiral assembly of polyfluorenes induced by chiral solvation: axial and supramolecular chirality . RSC Adv. , 2019 . 9 38257 -38264 . DOI:10.1039/C9RA08354Ehttp://doi.org/10.1039/C9RA08354E .

Watanabe, K.; Osaka, I.; Yorozuya, S.; Akagi, K. . Helically π-stacked thiophene-based copolymers with circularly polarized fluorescence: high dissymmetry factors enhanced by self-ordering in chiral nematic liquid crystal phase . Chem. Mater. , 2012 . 24 1011 -1024 . DOI:10.1021/cm2028788http://doi.org/10.1021/cm2028788 .

Oda, M.; Nothofer, H. G.; Scherf, U.; Sunjic, V.; Richter, D.; Regenstein, W.; Neher, D. . Chiroptical properties of chiral substituted polyfluorenes . Macromolecules , 2002 . 35 6792 -6798 . DOI:10.1021/ma020630ghttp://doi.org/10.1021/ma020630g .

Oda, M.; Nothofer, H. G.; Lieser, G.; Scherf, U.; Meskers, S. C. J.; Neher, D. . Circularly polarized electroluminescence from liquid-crystalline chiral polyfluorenes . Adv. Mater. , 2000 . 12 362 -365 . DOI:10.1002/(SICI)1521-4095(200003)12:5<362::AID-ADMA362>3.0.CO;2-Phttp://doi.org/10.1002/(SICI)1521-4095(200003)12:5<362::AID-ADMA362>3.0.CO;2-P .

Hu, J.; Li, X.; Ni, Y.; Ma, S. D.; Yu, H. F. . A programmable and biomimetic photo-actuator: a composite of a photo-liquefiable azobenzene derivative and commercial plastic film . J. Mater. Chem. C , 2018 . 6 10815 -10821 . DOI:10.1039/C8TC03693Dhttp://doi.org/10.1039/C8TC03693D .

Hu, J.; Huang, S.; Yu, M. M.; Yu, H. F. . Flexible solar thermal fuel devices: composites of fabric and a photoliquefiable azobenzene derivative . Adv. Energy Mater. , 2019 . 9 1901363 DOI:10.1002/aenm.201901363http://doi.org/10.1002/aenm.201901363 .

Cheng, Z. X.; Ma, S. D.; Zhang, Y. H.; Huang, S.; Chen, Y. X.; Yu, H. F. . Photomechanical motion of liquid-crystalline fibers bending away from a light source . Macromolecules , 2017 . 50 8317 -8324 . DOI:10.1021/acs.macromol.7b01741http://doi.org/10.1021/acs.macromol.7b01741 .

Yin, L.; Han, L.; Ge, F. J.; Tong, X.; Zhang, W.; Soldera, A.; Zhao, Y. . A novel side-chain liquid crystal elastomer exhibiting anomalous reversible shape change . Angew. Chem. Int. Ed. , 2020 . 59 15129 -15134 . DOI:10.1002/anie.202003904http://doi.org/10.1002/anie.202003904 .

Wang, H. P.; He, Y. N.; Tuo, X. L.; Wang, X. G. . Sequentially adsorbed electrostatic multilayers of branched side-chain polyelectrolytes bearing donor-acceptor type Azo chromophores . Macromolecules , 2004 . 37 135 -146 . DOI:10.1021/ma035208uhttp://doi.org/10.1021/ma035208u .

Wang, D. R.; Ye, G.; Zhu, Y.; Wang, X. G. . Photoinduced mass-migration behavior of two amphiphilic side-chain azo diblock copolymers with different length flexible spacers . Macromolecules , 2009 . 42 2651 -2657 . DOI:10.1021/ma8026063http://doi.org/10.1021/ma8026063 .

Li, Y. B.; He, Y. N.; Tong, X. L.; Wang, X. G. . Photoinduced deformation of amphiphilic azo polymer colloidal spheres . J. Am. Chem. Soc. , 2005 . 127 2402 -2403 . DOI:10.1021/ja0424981http://doi.org/10.1021/ja0424981 .

Li, N.; Li, Y. B.; Wang, X. G. . Fractal structures from amphiphilic random azo copolymer . Macromolecules , 2011 . 44 8598 -8606 . DOI:10.1021/ma200992nhttp://doi.org/10.1021/ma200992n .

Deng, Y. H.; Li, N.; He, Y. N.; Wang, X. G. . Hybrid colloids composed of two amphiphilic azo polymers: fabrication, characterization, and photoresponsive properties . Macromolecules , 2007 . 40 6669 -6678 . DOI:10.1021/ma0710481http://doi.org/10.1021/ma0710481 .

Yu, Y. L.; Maeda, T.; Mamiya, J.; Ikeda, T. . Photomechanical effects of ferroelectric liquid-crystalline elastomers containing azobenzene chromophores . Angew. Chem. Int. Ed. , 2007 . 46 881 -883 . DOI:10.1002/anie.200603053http://doi.org/10.1002/anie.200603053 .

Lv, J. A.; Liu, Y. Y.; Wei, J.; Chen, E. Q.; Qin, L.; Yu, Y. L. . Photocontrol of fluid slugs in liquid crystal polymer microactuators . Nature , 2016 . 537 179 -184 . DOI:10.1038/nature19344http://doi.org/10.1038/nature19344 .

Liu, Y. Y.; Xu, B.; Sun, S. T.; Wei, J.; Wu, L. M.; Yu, Y. L. . Humidity- and photo-induced mechanical actuation of cross-linked liquid crystal polymers . Adv. Mater. , 2017 . 29 1604792 DOI:10.1002/adma.201604792http://doi.org/10.1002/adma.201604792 .

Yamada, M.; Kondo, M.; Mamiya, J. I.; Yu, Y. L.; Kinoshita, M.; Barrett, C. J.; Ikeda, T. . Photomobile polymer materials: towards light-driven plastic motors . Angew. Chem. Int. Ed. , 2008 . 47 4986 -4988 . DOI:10.1002/anie.200800760http://doi.org/10.1002/anie.200800760 .

Jiang, S. Q.; Zhao, Y.; Wang, L.; Yin, L. B.; Zhang, Z. B.; Zhu, J.; Zhang, W.; Zhu, X. L. . Photocontrollable induction of supramolecular chirality in achiral side chain Azo-containing polymers through preferential chiral solvation . Polym. Chem. , 2015 . 6 4230 -4239 . DOI:10.1039/C5PY00496Ahttp://doi.org/10.1039/C5PY00496A .

Yin, L.; Liu, M.; Zhao, Y.; Zhang, S. S.; Zhang, W.; Zhang, Z. B. A.; Zhu, X. L. . Supramolecular chirality induced by chiral solvation in achiral cyclic Azo-containing polymers: topological effects on chiral aggregation . Polym. Chem. , 2018 . 9 769 -776 . DOI:10.1039/C7PY02002Chttp://doi.org/10.1039/C7PY02002C .

Yin, L.; Zhao, Y.; Jiang, S. Q.; Wang, L. B.; Zhang, Z. B.; Zhu, J.; Zhang, W.; Zhu, X. L. . Preferential chiral solvation induced supramolecular chirality in optically inactive star Azo polymers: photocontrollability, chiral amplification and topological effects . Polym. Chem. , 2015 . 6 7045 -7052 . DOI:10.1039/C5PY01175Bhttp://doi.org/10.1039/C5PY01175B .

Yin, L.; Zhao, Y.; Liu, M.; Zhou, N. C.; Zhang, W.; Zhu, X. L. . Induction of supramolecular chirality by chiral solvation in achiral Azo polymers with different spacer lengths and push-pull electronic substituents: where will chiral induction appear? . Polym. Chem. , 2017 . 8 1906 -1913 . DOI:10.1039/C7PY00130Dhttp://doi.org/10.1039/C7PY00130D .

Miao, T. F.; Yin, L.; Cheng, X. X.; Zhao, Y.; Hou, W. J.; Zhang, W.; Zhu, X. L. . Chirality construction from preferred π-π stacks of achiral azobenzene units in polymer: chiral induction, transfer and memory . Polymers , 2018 . 10 612 DOI:10.3390/polym10060612http://doi.org/10.3390/polym10060612 .

Molla, M. R.; Das, A.; Ghosh, S. . Chiral induction by helical neighbour: spectroscopic visualization of macroscopic-interaction among self-sorted donor and acceptor π-stacks . Chem. Commun. , 2011 . 47 8934 -8936 . DOI:10.1039/c1cc11178ghttp://doi.org/10.1039/c1cc11178g .

Edwards, W.; Smith, D. K. . Enantioselective component selection in multicomponent supramolecular gels . J. Am. Chem. Soc. , 2014 . 136 1116 -1124 . DOI:10.1021/ja411724rhttp://doi.org/10.1021/ja411724r .

Haino, T.; Tanaka, M.; Fukazawa, Y. . Self-assembly of tris(phenylisoxazolyl) benzene and its asymmetric induction of supramolecular chirality . Chem. Commun. , 2008 . 468 -470. .

Li, Y. G.; Wang, T. Y.; Liu, M. H. . Gelating-induced supramolecular chirality of achiral porphyrins: chiroptical switch between achiral molecules and chiral assemblies . Soft Matter , 2007 . 3 1312 -1317 . DOI:10.1039/b710165ahttp://doi.org/10.1039/b710165a .

Yang, D.; Zhao, Y.; Lv, K.; Wang, X. F.; Zhang, W.; Zhang, L.; Liu, M. H. . A strategy for tuning achiral main-chain polymers into helical assemblies and chiral memory systems . Soft Matter , 2016 . 12 1170 -1175 . DOI:10.1039/C5SM02547Hhttp://doi.org/10.1039/C5SM02547H .

Yang, D.; Zhang, L.; Yin, L.; Zhao, Y.; Zhang, W.; Liu, M. H. . Fabrication of chiroptically switchable films via co-gelation of a small chiral gelator with an achiral azobenzene-containing polymer . Soft Matter , 2017 . 13 6129 -6136 . DOI:10.1039/C7SM00935Fhttp://doi.org/10.1039/C7SM00935F .

Nikolova, L.; Nedelchev, L.; Todorov, T.; Petrova, T.; Tomova, N.; Dragostinova, V.; Ramanujam, P. S.; Hvilsted, S. . Self-induced light polarization rotation in azobenzene-containing polymers . Appl. Phys. Lett. , 2000 . 77 657 -659 . DOI:10.1063/1.127076http://doi.org/10.1063/1.127076 .

Choi, S. W.; Kawauchi, S.; Ha, N. Y.; Takezoe, H. . Photoinduced chirality in azobenzene-containing polymer systems . Phys. Chem. Chem. Phys. , 2007 . 9 3671 -3681 . DOI:10.1039/b702835khttp://doi.org/10.1039/b702835k .

Iftime, G.; Labarthet, F. L.; Natansohn, A.; Rochon, P. . Control of chirality of an azobenzene liquid crystalline polymer with circularly polarized light . J. Am. Chem. Soc. , 2000 . 122 12646 -12650 . DOI:10.1021/ja001244mhttp://doi.org/10.1021/ja001244m .

Kim, M. J.; Shin, B. G.; Kim, J. J.; Kim, D. Y. . Photoinduced supramolecular chirality in amorphous azobenzene polymer films . J. Am. Chem. Soc. , 2002 . 124 3504 -3505 . DOI:10.1021/ja017454whttp://doi.org/10.1021/ja017454w .

Takezoe, H.; Takanishi, Y. . Bent-core liquid crystals: their mysterious and attractive world . Jpn. J. Appl. Phys. , 2006 . 45 597 -625 . DOI:10.1143/JJAP.45.597http://doi.org/10.1143/JJAP.45.597 .

Zou, G.; Jiang, H.; Kohn, H.; Manaka, T.; Iwamoto, M. . Control and modulation of chirality for azobenzene-substituted polydiacetylene LB films with circularly polarized light . Chem. Commun. , 2009 . 5627 -5629. .

Angiolini, L.; Benelli, T.; Giorgini, L.; Salatelli, E.; Bozio, R.; Dauru, A.; Pedron, D. . Improvement of photoinduced birefringence properties of optically active methacrylic polymers through copolymerization of monomers bearing azoaromatic moieties . Macromolecules , 2006 . 39 489 -497 . DOI:10.1021/ma052232uhttp://doi.org/10.1021/ma052232u .

Fujiki, M.; Yoshida, K.; Suzuki, N.; Zhang, J.; Zhang, W.; Zhu, X. L. . Mirror symmetry breaking and restoration within μm-sized polymer particles in optofluidic media by pumping circularly polarised light . RSC Adv. , 2013 . 3 5213 -5219 . DOI:10.1039/c3ra22709jhttp://doi.org/10.1039/c3ra22709j .

Fujiki, M.; Donguri, Y.; Zhao, Y.; Nakao, A.; Suzuki, N.; Yoshida, K.; Zhang, W. . Photon magic: chiroptical polarisation, depolarisation, inversion, retention and switching of non-photochromic light-emitting polymers in optofluidic medium . Polym. Chem. , 2015 . 6 1627 -1638 . DOI:10.1039/C4PY01337Ahttp://doi.org/10.1039/C4PY01337A .

Nakano, T. . Tricks of light on helices: transformation of helical polymers by photoirradiation . Chem. Rec. , 2014 . 14 369 -385 . DOI:10.1002/tcr.201300042http://doi.org/10.1002/tcr.201300042 .

Wang, Y.; Harada, T.; Phuong, L. Q.; Kanemitsu, Y.; Nakano, T. . Helix induction to polyfluorenes using circularly polarized light: chirality amplification, phase-selective induction, and anisotropic emission . Macromolecules , 2018 . 51 6865 -6877 . DOI:10.1021/acs.macromol.8b01453http://doi.org/10.1021/acs.macromol.8b01453 .

Wang, L. B.; Yin, L.; Zhang, W.; Zhu, X. L.; Fujiki, M. . Circularly polarized light with sense and wavelengths to regulate azobenzene supramolecular chirality in optofluidic medium . J. Am. Chem. Soc. , 2017 . 139 13218 -13226 . DOI:10.1021/jacs.7b07626http://doi.org/10.1021/jacs.7b07626 .

van, Delden R. A.; Feringa, B. L. . Color indicators of molecular chirality based on doped liquid crystals . Angew. Chem. Int. Ed. , 2001 . 40 3198 -3200 . DOI:10.1002/1521-3773(20010903)40:17<3198::AID-ANIE3198>3.0.CO;2-Ihttp://doi.org/10.1002/1521-3773(20010903)40:17<3198::AID-ANIE3198>3.0.CO;2-I .

Lemieux, R. P. . Chirality transfer in ferroelectric liquid crystals . Acc. Chem. Res. , 2001 . 34 845 -853 . DOI:10.1021/ar9901164http://doi.org/10.1021/ar9901164 .

Ma, J.; Li, Y. N.; White, T.; Urbas, A.; Li, Q. . Light-driven nanoscale chiral molecular switch: reversible dynamic full range color phototuning . Chem. Commun. , 2010 . 46 3463 -3465 . DOI:10.1039/c002436hhttp://doi.org/10.1039/c002436h .

Yao, L.; Lu, X.; Chen, S.; Watkins, J. J. . Formation of helical phases in achiral block copolymers by simple addition of small chiral additives . Macromolecules , 2014 . 47 6547 -6553 . DOI:10.1021/ma501714ghttp://doi.org/10.1021/ma501714g .

Zhang, W.; Fujiki, M.; Zhu, X. L. . Chiroptical nanofibers generated from achiral metallophthalocyanines induced by diamine homochirality . Chem. Eur. J. , 2011 . 17 10628 -10635 . DOI:10.1002/chem.201100208http://doi.org/10.1002/chem.201100208 .

Cheng, X. X.; Miao, T. F.; Ma, H. T.; Yin, L.; Zhang, W.; Zhang, Z. B.; Zhu, X. L. . The construction of photoresponsive polymer particles with supramolecular helicity from achiral monomers by helix-sense-selective polymerization . Polym. Chem. , 2020 . 11 2089 -2097 . DOI:10.1039/C9PY01868Ahttp://doi.org/10.1039/C9PY01868A .

Schwartz, E.; Le, Gac S.; Cornelissen, J. J. L. M.; Nolte, R. J. M.; Rowan, A. E. . Macromolecular multi-chromophoric scaffolding . Chem. Soc. Rev. , 2010 . 39 1576 -1599 . DOI:10.1039/b922160chttp://doi.org/10.1039/b922160c .

Haraguchi, S.; Hasegawa, T.; Numata, M.; Fujiki, M.; Uezu, K.; Sakurai, K.; Shinkai, S. . Oligosilane-nanofibers can be prepared through fabrication of permethyldecasilane within a helical superstructure of schizophyllan . Org. Lett. , 2005 . 7 5605 -5608 . DOI:10.1021/ol052170shttp://doi.org/10.1021/ol052170s .

Numata, M.; Hasegawa, T.; Fujisawa, T.; Sakurai, K.; Shinkai, S. . Beta-1,3-glucan (Schizophyllan) can act as a one-dimensional host for creation of novel poly(aniline) nanofiber structures . Org. Lett. , 2004 . 6 4447 -4450 . DOI:10.1021/ol0483448http://doi.org/10.1021/ol0483448 .

Li, C.; Numata, M.; Bae, A. H.; Sakurai, K.; Shinkai, S. . Self-assembly of supramolecular chiral insulated molecular wire . J. Am. Chem. Soc. , 2005 . 127 4548 -4549 . DOI:10.1021/ja050168qhttp://doi.org/10.1021/ja050168q .

Guo, S. B.; Suzuki, N.; Fujiki, M. . Oligo- and polyfluorenes meet cellulose alkyl esters: Retention, inversion, and racemization of circularly polarized luminescence (CPL) and circular dichroism (CD) via intermolecular C-H/O=C interactions . Macromolecules , 2017 . 50 1778 -1789 . DOI:10.1021/acs.macromol.6b02762http://doi.org/10.1021/acs.macromol.6b02762 .

Lan, X.; Liu, T. J.; Wang, Z. M.; Govorov, A. O.; Yan, H.; Liu, Y. . DNA-guided plasmonic helix with switchable chirality . J. Am. Chem. Soc. , 2018 . 140 11763 -11770 . DOI:10.1021/jacs.8b06526http://doi.org/10.1021/jacs.8b06526 .

Duong, S. T.; Fujiki, M. . The origin of bisignate circularly polarized luminescence (CPL) spectra from chiral polymer aggregates and molecular camphor: anti-Kasha's rule revealed by CPL excitation (CPLE) spectra . Polym. Chem. , 2017 . 8 4673 -4679 . DOI:10.1039/C7PY00958Ehttp://doi.org/10.1039/C7PY00958E .

Fujiki, M.; Yoshimoto, S. . Time-evolved, far-red, circularly polarised luminescent polymer aggregates endowed with sacrificial helical Si-Si bond polymers . Mater. Chem. Front. , 2017 . 1 1773 -1785 . DOI:10.1039/C7QM00096Khttp://doi.org/10.1039/C7QM00096K .

Rahim, N. A. A.; Fujiki, M. . Aggregation-induced scaffolding: Photoscissable helical polysilane generates circularly polarized luminescent polyfluorene . Polym. Chem. , 2016 . 7 4618 -4629 . DOI:10.1039/C6PY00595Khttp://doi.org/10.1039/C6PY00595K .

Chen, H. L.; Yin, L.; Liu, M.; Wang, L. B.; Fujiki, M.; Zhang, W.; Zhu, X. L. . Aggregation-induced chiroptical generation and photoinduced switching of achiral azobenzene-alt-fluorene copolymer endowed with left- and right-handed helical polysilanes . RSC Adv. , 2019 . 9 4849 -4856 . DOI:10.1039/C8RA09345Hhttp://doi.org/10.1039/C8RA09345H .

Lu, H. H.; Liu, C. Y.; Chang, C. H.; Chen, S. A. . Self-dopant formation in poly(9,9-di-n-octylfluorene) via a dipping method for efficient and stable pure-blue electrolumineseence . Adv. Mater. , 2007 . 19 2574 -2579 . DOI:10.1002/adma.200602632http://doi.org/10.1002/adma.200602632 .

Ruiz, U.; Pagliusi, P.; Provenzano, C.; Shibaev, V. P.; Cipparrone, G. . Supramolecular chiral structures: smart polymer organization guided by 2D polarization light patterns . Adv. Funct. Mater. , 2012 . 22 2964 -2970 . DOI:10.1002/adfm.201200389http://doi.org/10.1002/adfm.201200389 .

Zhang, L.; Wang, H. X.; Li, S.; Liu, M. H. . Supramolecular chiroptical switches . Chem. Soc. Rev. , 2020 . DOI:10.1039/d0cs00191khttp://doi.org/10.1039/d0cs00191k .

Kumar, J.; Nakashima, T.; Kawai, T. . Circularly polarized luminescence in chiral molecules and supramolecular assemblies . J. Phys. Chem. Lett. , 2015 . 6 3445 -3452 . DOI:10.1021/acs.jpclett.5b01452http://doi.org/10.1021/acs.jpclett.5b01452 .

Sang, Y. T.; Han, J. L.; Zhao, T. H.; Duan, P. F.; Liu, M. H. . Circularly polarized luminescence in nanoassemblies: generation, amplification, and application . Adv. Mater. , 2020 . 32 1900110 DOI:10.1002/adma.201900110http://doi.org/10.1002/adma.201900110 .

Cheng, X. X.; Miao, T. F.; Yin, L.; Ji, Y. J.; Li, Y. Y.; Zhang, Z. B.; Zhang, W.; Zhu, X. L. . In situ controlled construction of a hierarchical supramolecular chiral liquid-crystalline polymer assembly . Angew. Chem. Int. Ed. , 2020 . 59 9669 -9677 . DOI:10.1002/anie.202001657http://doi.org/10.1002/anie.202001657 .

Chen, J. X.; Cai, S. L.; Wang, R.; Wang, S.; Zhang, J.; Wan, X. H. . Polymerization-induced self-assembly of conjugated block copoly(phenylacetylene)s . Macromolecules , 2020 . 53 1638 -1644 . DOI:10.1021/acs.macromol.9b02504http://doi.org/10.1021/acs.macromol.9b02504 .

Jimaja, S.; Varlas, S.; Xie, Y. J.; Foster, J. C.; Taton, D.; Dove, A. P.; O'Reilly, R. K. . Nickel-catalyzed coordination polymerization-induced self-assembly of helical poly(aryl isocyanide)s . ACS Macro Lett. , 2020 . 9 226 -232 . DOI:10.1021/acsmacrolett.9b00972http://doi.org/10.1021/acsmacrolett.9b00972 .

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