journal article·2023-01

Recent advances in chiral AIE polymers

Qing Xia, Anjun Qin, Ben Zhong Tang

Journal of Nanoparticle Research· Volume 25· Issue 1
Publisher page

Abstract

In recent years, chiral AIE polymers have gained widespread interests because of their superior luminescent properties and a wide range of potential applications. The efforts in this area have been put on the development of new types of AIE polymers with chiral properties, and the improvement of their circular dichroism and circularly polarized luminescence with high chiral luminescence asymmetry factor (g(lum)). This review summarizes recent progress in the development of chiral AIE polymers by dividing them into intrinsic chirality, self-assembly induced chirality and exogenous species induced chirality. Meanwhile, a brief outlook is given on the current challenges and future directions for the development of chiral AIE polymers.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Synthesis and Properties of Aromatic Compounds · Luminescence and Fluorescent Materials · Perovskite Materials and Applications

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (58)

Show source-provided references
1. Liu X, Jiao J, Jiang X, Li J, Cheng Y, Zhu C (2013) A tetraphenylethene-based chiral polymer: an aie luminogen with high and tunable CPL dissymmetry factor. J Mater Chem C 1:4713–471910.1039/c3tc30886c ↗
2. Qiu Z, Liu X, Lam JWY, Tang BZ (2019) The marriage of aggregation-induced emission with polymer science. Macromol Rapid Commun 40:180056810.1002/marc.201800568 ↗
3. Thomas SW, Joly GD, Swager TM (2007) Chemical sensors based on amplifying fluorescent conjugated polymers. Chem Rev 107:1339–138610.1021/cr0501339 ↗
4. Tang BZ, Zhan X, Yu G, Lee SPP, Liu Y, Zhu D (2001) Efficient blue emission from siloles. J Mater Chem 11:2974–297810.1039/b102221k ↗
5. Luo J, Xie Z, Lam JWY, Cheng L, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D, Tang BZ (2001) Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem Commun 1740–1741.10.1039/b105159h ↗
6. Mei J, Leung NLC, Kwok RTK, Lam JWY, Tang BZ (2015) Aggregation-induced emission: together we shine, united we soar! Chem Rev 115:11718–1194010.1021/acs.chemrev.5b00263 ↗
7. Hu R, Qin AJ, Tang BZ (2020) AIE polymers: synthesis and applications. Prog Polym Sci 100:10117610.1016/j.progpolymsci.2019.101176 ↗
8. Hu R, Kang Y, Tang BZ (2016) Recent advances in AIE polymers. Polym J 48:359–37010.1038/pj.2016.1 ↗
9. Su X, Gao Q, Wang D, Han T, Tang BZ (2021) One-step multicomponent polymerizations for the synthesis of multifunctional AIE polymers. Macromol Rapid Commun 42:200047110.1002/marc.202000471 ↗
10. Zhan R, Pan Y, Manghnani PN, Liu B (2017) AIE polymers: synthesis, properties, and biological applications. Macromol Biosci 17:160043310.1002/mabi.201600433 ↗
11. Hu R, Yang X, Qin A, Tang BZ (2021) AIE polymers in sensing, imaging and theranostic applications. Mater Chem Front 5:4073–408810.1039/D1QM00078K ↗
12. Roose J, Tang BZ, Wong KS (2016) Circularly-polarized luminescence (CPL) from chiral AIE molecules and macrostructures. Small 12:6495–651210.1002/smll.201601455 ↗
13. Li H, Li BS, Tang BZ (2019) Molecular design, circularly polarized luminescence, and helical self-assembly of chiral aggregation-induced emission molecules. Chem Asian J 14:674–68810.1002/asia.201801469 ↗
14. Liu C, Yang JC, Lam JWY, Feng HT, Tang BZ (2022) Chiral assembly of organic luminogens with aggregation-induced emission. Chem Sci 13:611–63210.1039/D1SC02305E ↗
15. Autho (2010) Circularly polarized luminescence (CPL) of proteins and protein complexes. In: Geddes CD (ed) Reviews in Fluorescence 2008. Springer, New York, New York, NY, pp 425–459
16. Chen SH, Katsis D, Schmid AW, Mastrangelo JC, Tsutsui T, Blanton TN (1999) Circularly Polarized Light Generated by Photoexcitation of Luminophores in Glassy Liquid-Crystal Films. Nature 397:506–50810.1038/17343 ↗
17. Montali A, Bastiaansen C, Smith P, Weder C (1998) Polarizing energy transfer in photoluminescent materials for display applications. Nature 392:261–26410.1038/32616 ↗
18. Peng QC, Luo XM, Qin YJ, Wang T, Bai B, Wei XL, Li K, Zang SQ (2022) Influence of Wallach’s rule on chiral AIE systems and its application in cryptographic information storage. CCS Chem 4:3686–369210.31635/ccschem.022.202201998 ↗
19. Sánchez-Carnerero EM, Agarrabeitia AR, Moreno F, Maroto BL, Muller G, Ortiz MJ, de la Moya S (2015) Circularly polarized luminescence from simple organic molecules. Chem Eur J 21:13488–1350010.1002/chem.201501178 ↗
20. Kumar J, Nakashima T, Kawai T (2015) Circularly polarized luminescence in chiral molecules and supramolecular assemblies. J Phys Chem Lett 6:3445–345210.1021/acs.jpclett.5b01452 ↗
21. Watanabe K, Sakamoto T, Taguchi M, Fujiki M, Nakano T (2011) A chiral π-stacked vinyl polymer emitting white circularly polarized light. Chem Commun 47:10996–1099810.1039/c1cc13711e ↗
22. Jiang X, Liu X, Jiang Y, Quan Y, Cheng Y, Zhu C (2014) Fluorescence study of chiral β-ketoiminate-based newly synthesized boron hybrid polymers. Macromol Chem Phys 215:358–36410.1002/macp.201300569 ↗
23. Chen Y, Lu P, Yuan Y, Zhang H (2020) Preparation and property manipulation of high efficiency circularly polarized luminescent liquid crystal polypeptides. J Mater Chem C 8:13632–1364110.1039/D0TC03276J ↗
24. Hu Y, Song F, Xu Z, Tu Y, Zhang H, Cheng Q, Lam JWY, Ma D, Tang BZ (2019) Circularly polarized luminescence from chiral conjugated poly(carbazole-ran-acridine)s with aggregation-induced emission and delayed fluorescence. ACS Appl Polym Mater 1:221–22910.1021/acsapm.8b00118 ↗
25. Ma X, Azeem EA, Liu X, Cheng Y, Zhu C (2014) Synthesis and Tunable Chiroptical Properties of Chiral BODIPY-based D–π–A Conjugated Polymers. J Mater Chem C 2:1076–108410.1039/C3TC32029D ↗
26. Kokado K, Tokoro Y, Chujo Y (2009) Luminescent and axially chiral Π-conjugated polymers linked by carboranes in the main chain. Macromolecules 42:9238–924210.1021/ma902094u ↗
27. Wang Z, Liu S, Wang Y, Quan Y, Cheng Y (2017) Tunable AICPL of (S)-binaphthyl-based three-component polymers via FRET mechanism. Macromol Rapid Commun 38:170015010.1002/marc.201700150 ↗
28. Wang Z, Fang Y, Tao X, Wang Y, Quan Y, Zhang S, Cheng Y (2017) Deep red aggregation-induced CPL emission behavior of four-component tunable AIE-active chiral polymers via two FRET pairs mechanism. Polymer 130:61–6710.1016/j.polymer.2017.09.072 ↗
29. Zhang H, Li H, Wang J, Sun J, Qin AJ, Tang BZ (2015) Axial chiral aggregation-induced emission luminogens with aggregation-annihilated circular dichroism effect. J Mater Chem C 3:5162–516610.1039/C5TC00629E ↗
30. Zhang H, Zheng X, Kwok RTK, Wang J, Leung NLC, Shi L, Sun JZ, Tang Z, Lam JWY, Qin A, Tang BZ (2018) In situ monitoring of molecular aggregation using circular dichroism. Nat Commun 9:496110.1038/s41467-018-07299-3 ↗
31. Yang L, Zhang Y, Zhang X, Li N, Quan Y, Cheng Y (2018) Doping-free circularly polarized electroluminescence of AIe-active chiral binaphthyl-based polymers. Chem Commun 54:9663–966610.1039/C8CC05153D ↗
32. Stará IG, Starý I (2020) Helically chiral aromatics: the synthesis of helicenes by [2 + 2 + 2] cycloisomerization of Π-electron systems. Acc Chem Res 53:144–15810.1021/acs.accounts.9b00364 ↗
33. Shen Y, Chen CF (2012) Helicenes: synthesis and applications. Chem Rev 112:1463–153510.1021/cr200087r ↗
34. Kawashima T, Matsumoto Y, Sato T, Yamada YMA, Kono C, Tsurusaki A, Kamikawa K (2020) Synthesis, structure, and complexation of an S-shaped double azahelicene with inner-edge nitrogen atoms. Chem Eur J 26:13170–1317610.1002/chem.202002405 ↗
35. Wang JY, Tang Y, Wu GZ, Zhang S, Rouh H, Jin S, Xu T, Wang Y, Unruh D, Surowiec K, Ma Y, Li Y, Katz C, Liang H, Cong W, Li G (2022) Asymmetric catalytic assembly of triple-columned and multilayered chiral folding polymers showing aggregation-induced emission (AIE). Chem Eur J 28:e20210410210.1002/chem.202104102 ↗
36. Zhang S, Sheng Y, Wei G, Quan Y, Cheng Y, Zhu C (2015) Aggregation-induced circularly polarized luminescence of an (R)-binaphthyl-based AIE-active chiral conjugated polymer with self-assembled helical nanofibers. Polym Chem 6:2416–242210.1039/C4PY01689K ↗
37. Ma J, Wang Y, Li X, Yang L, Quan Y, Cheng Y (2018) Aggregation-induced CPL response from chiral binaphthyl-based AIE-active polymers via supramolecular self-assembled helical nanowires. Polymer 143:184–18910.1016/j.polymer.2018.04.006 ↗
38. Xu L, Xu XH, Liu N, Zou H, Wu ZQ (2018) A facile synthetic route to multifunctional poly(3-hexylthiophene)-b-poly(phenyl isocyanide) copolymers: from aggregation-induced emission to controlled helicity. Macromolecules 51:7546–755510.1021/acs.macromol.8b01478 ↗
39. Zhang C, Li M, Lu HY, Chen CF (2018) Synthesis, chiroptical properties, and self-assembled nanoparticles of chiral conjugated polymers based on optically stable helical aromatic esters. RSC Adv 8:1014–102110.1039/C7RA12652B ↗
40. Liu Q, Xia Q, Wang S, Li BS, Tang BZ (2018) In situ visualizable self-assembly, aggregation-induced emission and circularly polarized luminescence of tetraphenylethene and alanine-based chiral polytriazole. J Mater Chem C 6:4807–481610.1039/C8TC00838H ↗
41. Lee S, Kim KY, Jung SH, Lee JH, Yamada M, Sethy R, Kawai T, Jung JH (2019) Finely controlled circularly polarized luminescence of a mechano-responsive supramolecular polymer. Angew Chem Int Ed 58:18878–1888210.1002/anie.201911380 ↗
42. Sun H, Luo Q, Hou C, Liu J (2017) Nanostructures based on protein self-assembly: from hierarchical construction to bioinspired materials. Nano Today 14:16–4110.1016/j.nantod.2017.04.006 ↗
43. Liu CZ, Koppireddi S, Wang H, Zhang DW, Li ZT (2019) Halogen bonding directed supramolecular quadruple and double helices from hydrogen-bonded arylamide foldamers. Angew Chem Int Ed 58:226–23010.1002/anie.201811561 ↗
44. Wijnands SPW, Engelen W, Lafleur RPM, Meijer EW, Merkx M (2018) Controlling protein activity by dynamic recruitment on a supramolecular polymer platform. Nat Commun 9:6510.1038/s41467-017-02559-0 ↗
45. Liu J, Luo Z, Yu L, Zhang P, Wei H, Yu Y (2020) A new soft-matter material with old chemistry: passerini multicomponent polymerization-induced assembly of AIE-active double-helical polymers with rapid visible-light degradability. Chem Sci 11:8224–823010.1039/D0SC02729D ↗
46. Bao Y, Luo Z, Cui S (2020) Environment-dependent single-chain mechanics of synthetic polymers and biomacromolecules by atomic force microscopy-based single-molecule force spectroscopy and the implications for advanced polymer materials. Chem Soc Rev 49:2799–282710.1039/C9CS00855A ↗
47. Wei G, Jiang Y, Wang F (2020) A achiral aiee-active polymer-Cu(Ii) complex sensor for highly selective and enantioselective recognition of histidine. Tetrahedron Lett 61:15172210.1016/j.tetlet.2020.151722 ↗
48. Liu Q, Xia Q, Xiong Y, Li BS, Tang BZ (2020) Circularly polarized luminescence and tunable helical assemblies of aggregation-induced emission amphiphilic polytriazole carrying chiral L-phenylalanine pendants. Macromolecules 53:6288–629810.1021/acs.macromol.0c01140 ↗
49. Wang L, Suzuki N, Liu J, Matsuda T, Rahim NAA, Zhang W, Fujiki M, Zhang Z, Zhou N, Zhu X (2014) Limonene induced chiroptical generation and inversion during aggregation of achiral polyfluorene analogs: structure-dependence and mechanism. Polym Chem 5:5920–592710.1039/C4PY00865K ↗
50. Lu N, Gao X, Pan M, Zhao B, Deng J (2020) Aggregation-induced emission-active chiral helical polymers show strong circularly polarized luminescence in thin films. Macromolecules 53:8041–804910.1021/acs.macromol.0c00638 ↗
51. Zhao B, Pan K, Deng J (2019) Combining chiral helical polymer with achiral luminophores for generating full-color, on–off, and switchable circularly polarized luminescence. Macromolecules 52:376–38410.1021/acs.macromol.8b02305 ↗
52. Zhao B, Yu H, Pan K, Za T, Deng J (2020) Multifarious chiral nanoarchitectures serving as handed-selective fluorescence filters for generating full-color circularly polarized luminescence. ACS Nano 14:3208–321810.1021/acsnano.9b08618 ↗
53. Akagi K (2019) Interdisciplinary chemistry based on integration of liquid crystals and conjugated polymers: development and progress. Bull Chem Soc Jpn 92:1509–165510.1246/bcsj.20190092 ↗
54. Li X, Hu W, Wang Y, Quan Y, Cheng Y (2019) Strong CPL of Achiral AIE-Active Dyes Induced by Supramolecular Self-Assembly in Chiral Nematic Liquid Crystals (AIE-N*-LCs). Chem Commun 55:5179–518210.1039/C9CC01678C ↗
55. Chen Y, Lu P, Li Z, Yuan Y, Zhang H (2021) Side-chain chiral fluorescent liquid crystal polymers with highly efficient circularly polarized luminescence emission in a glassy-state Smc* film. Polym Chem 12:2572–257910.1039/D1PY00199J ↗
56. Ban JF, Chen S, Zhang HL (2015) Synthesis and liquid crystalline behavior of side chain liquid crystalline polymers containing triphenylene discotic mesogens with different length flexible spacers. Chin J Polym Sci 33:1245–125910.1007/s10118-015-1672-5 ↗
57. Luo ZW, Tao L, Zhong CL, Li ZX, Lan K, Feng Y, Wang P, Xie HL (2020) High-efficiency circularly polarized luminescence from chiral luminescent liquid crystalline polymers with aggregation-induced emission properties. Macromolecules 53:9758–976810.1021/acs.macromol.0c02246 ↗
58. Liu K, Shen Y, Li X, Zhang Y, Quan Y, Cheng Y (2020) Strong CPL of achiral liquid crystal fluorescent polymer via the regulation of AIE-active chiral dopant. Chem Commun 56:12829–1283210.1039/D0CC05523A ↗