One-handed Helical Poly(<italic style="font-style: italic">m</italic>-terphenyl acetylene)s with Broad Optical Activity Range from Ultraviolet-Visible to Near-infrared Regions

Li-Yuan Shi; Fu Tian; Cheng-Yin Cao; Kun Hu; Xiao-Die Zhu; Xiao-Hong Li; Sheng Wang

doi:10.1007/s10118-026-3656-z

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One-handed Helical Poly(m-terphenyl acetylene)s with Broad Optical Activity Range from Ultraviolet-Visible to Near-infrared Regions

Special Topic: Chirality in Polymers | Updated：2026-08-31

- One-handed Helical Poly(m-terphenyl acetylene)s with Broad Optical Activity Range from Ultraviolet-Visible to Near-infrared Regions
- One-handed Helical Poly(m-terphenyl acetylene)s with Broad Optical Activity Range from Ultraviolet-Visible to Near-infrared Regions
- Chinese Journal of Polymer Science 2026年44卷第9期页码：2843-2853
- Affiliations：
  
  Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
- Author bio：
  
  wangsheng@suda.edu.cn
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (Nos. 52473017 and 52103001) and the Natural Science Foundation of Jiangsu Higher Education Institutions of China (No. 22KJA150005).;The authors declare no interest conflict.Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-026-3656-z.The data supporting the findings of this study are available from the corresponding author upon reasonable request.
- DOI：10.1007/s10118-026-3656-z
  中图分类号：
- 收稿：2026-02-11，
  
  录用：2026-03-11，
  
  网络首发：2026-06-22，
  
  纸质出版：2026-09-05
- Accepted：
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Shi, L. Y.; Tian, F.; Cao, C. Y.; Hu K.; Zhu, X. D.; Li, X. H.; Wang, S. One-handed helical poly(m-terphenyl acetylene)s with broad optical activity range from ultraviolet-visible to near-infrared regions. Chinese J. Polym. Sci. 2026, 44, 2843–2853

Li-Yuan Shi, Fu Tian, Cheng-Yin Cao, et al. One-handed Helical Poly(m-terphenyl acetylene)s with Broad Optical Activity Range from Ultraviolet-Visible to Near-infrared Regions[J]. Chinese Journal of Polymer Science, 2026, 44(9): 2843-2853. DOI: 10.1007/s10118-026-3656-z.
Shi, L. Y.; Tian, F.; Cao, C. Y.; Hu K.; Zhu, X. D.; Li, X. H.; Wang, S. One-handed helical poly(m-terphenyl acetylene)s with broad optical activity range from ultraviolet-visible to near-infrared regions. Chinese J. Polym. Sci. 2026, 44, 2843–2853 DOI： 10.1007/s10118-026-3656-z.

Li-Yuan Shi, Fu Tian, Cheng-Yin Cao, et al. One-handed Helical Poly(m-terphenyl acetylene)s with Broad Optical Activity Range from Ultraviolet-Visible to Near-infrared Regions[J]. Chinese Journal of Polymer Science, 2026, 44(9): 2843-2853. DOI: 10.1007/s10118-026-3656-z. DOI：

摘要

A series of poly(

-terphenyl acetylene)s was prepared

in which large

-terphenyl units were directly linked to the polyene backbone

thereby significantly enhancing the steric repulsion between side groups to afford stretched poly(phenylacetylene)s with large conjugated lengths and near-infrared optical activity.

Abstract

Poly(phenylacetylene)s (PPAs) are one kind of important helical polymers with tunable main chain conformations. However

the preparation of near-infrare

d optically active helical PPAs remains a challenge. Here

we report a novel helical poly(

-terphenyl acetylene)s (PTPAs) bearing two chiral alkylamide pendants

which showed a stretched

cis-transoid

helix in solution or poly(methyl methacrylate) matrix with a broad optical activity range from the ultraviolet-visible (UV-Vis) to near-infrared regions. The effects of substituents

solvents

temperature

and acid/base additions on the helical conformation were carefully investigated. The substituent structure had little effect on the elongation but remarkably affected the main chain screw sense. The stability of this extended

cis-transoid

helix depends on the solvent applied and the temperature. Reversible conformational transitions between the one-handed

cis-transoid

helices and frustrated coil conformations can be achieved by the addition of trifluoroacetic acid and triethylamine. Furthermore

full-color circularly polarized luminescent materials can be prepared by virtue of their broad Cotton effects and chirality-selective absorption.

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Choi, H. K.; Min, D.; Kang, H.; Shon, M. J.; Rah, S. H.; Kim, H. C.; Jeong, H.; Choi, H. J.; Bowie, J. U.; Yoon, T. Y. Watching helical membrane proteins fold reveals a common N-to-C-terminal folding pathway. Science 2019 , 366 , 1150−1156..

Ferry, G. The structure of DNA. Nature 2019 , 575 , 35−36..

Gao, R. T.; Li, S. Y.; Liu, N.; Liu, B. H.; Wu, Z. Q. Helical polymers: from precise synthesis to structures and functions. Chem. Rev. 2026 , 126 , 297−403..

Lago-Silva, M.; Fernandez-Miguez, M.; Rodriguez, R.; Quinoa, E.; Freire, F. Stimuli-responsive synthetic helical polymers. Chem. Soc. Rev. 2024 , 53 , 793−852..

Yashima, E.; Ousaka, N.; Taura, D.; Shimomura, K.; Ikai, T.; Maeda, K. Supramolecular helical systems: helical assemblies of small molecules, foldamers, and polymers with chiral amplification and their functions. Chem. Rev. 2016 , 116 , 13752−13990..

[Shi, L.; Tian, F.; Wang, S. “Sergeants-and-soldiers” effect and modified Ising model in chiral polymer materials. Sci. China Chem . 2025, 68 , 3429−3448..

Li, J.; Wang, S.; Lu, H.; Tu, Y.; Wan, X.; Li, X.; Tu, Y.; Li, C. Y. Helical crystals in aliphatic copolyesters: from chiral amplification to mechanical property enhancement. ACS Macro Lett. 2023 , 12 , 369−375..

Gao, L.; Liao, R.; Ao, L.; Zhang, Y.; Jin, J.; Wang, F. Enhancing circularly polarized luminescence of anthraquinones via J-type supramolecular polymerization. Angew. Chem. Int. Ed. 2025 , 64 , e202505776..

Hirose, D.; Isobe, A.; Quinoa, E.; Freire, F.; Maeda, K. Three-state switchable chiral stationary phase based on helicity control of an optically active poly(phenylacetylene) derivative by using metal cations in the solid state. J. Am. Chem. Soc. 2019 , 141 , 8592−8598..

Ikai, T.; Matsumoto, T.; Takeda, S.; Oki, K.; Yashima, E. Tunable synthesis of one-handed helical ladder polymers with a helical cavity or helical grooves for advanced chiral recognition. Macromolecules 2025 , 58 , 6943−6952..

Ikai, T.; Ito, M.; Oki, K.; Suzuki, N.; Yashima, E. One-handed helical polyacetylenes bearing axially-chiral 2-arylpyridyl-N-oxide units for efficient chromatographic enantioseparation of chiral aromatic and aliphatic alcohols. Angew. Chem. Int. Ed. 2023 , 62 , e202306252..

Xu, L.; Wu, Y. J.; Gao, R. T.; Li, S. Y.; Liu, N.; Wu, Z. Q. Visible helicity induction and memory in polyallene toward circularly polarized luminescence, helicity discrimination, and enantiomer separation. Angew. Chem. Int. Ed. 2023 , 62 , e202217234..

Maeda, K.; Hirose, D.; Nozaki, M.; Shimizu, Y.; Mori, T.; Yamanaka, K.; Ogino, K.; Nishimura, T.; Taniguchi, T.; Moro, M.; Yashima, E. Helical springs as a color indicator for determining chirality and enantiomeric excess. Sci. Adv. 2021 , 7 , eabg5381..

Yamawaki, T.; Kuroda, T.; Yamamoto, T.; Nagata, Y.; Suginome, M. Helical poly(quioxaline-2,3-diyl)-based poly(carboxylic acid)s as a chiroptical chemosensor for detection and quantification of small enantiomeric Imbalances of chiral amines in water. ACS Macro Lett. 2025 , 14 , 272−277..

Gao, R. T.; Yu, J. X.; Ti, Q. H.; Mo, M. Y.; Liu, N.; Wu, Z. Q. Precise synthesis of racemate-based one-handed helical polymers as recyclable homogeneous chiral catalysts for multiple asymmetric reactions. J. Am. Chem. Soc. 2025 , 147 , 37521−37533..

Xu, L.; Zhou, L.; Li, Y. X.; Gao, R. T.; Chen, Z.; Liu, N.; Wu, Z. Q. Thermo-responsive chiral micelles as recyclable organocatalyst for asymmetric Rauhut-Currier reaction in water. Nat. Commun. 2023 , 14 , 7287..

Ikai, T.; Ando, M.; Ito, M.; Ishidate, R.; Suzuki, N.; Maeda, K.; Yashima, E. Emergence of highly enantioselective catalytic activity in a helical polymer mediated by deracemization of racemic pendants. J. Am. Chem. Soc. 2021 , 143 , 12725−12735..

Zhong, H.; Zhao, B.; Deng, J. Solvent-dependent chirality transmission and amplification from cellulose derivative to achiral helical polymer for achieving full-color and white circularly polarized luminescence. Angew. Chem. Int. Ed. 2025 , 64 , e202418463..

Yang, K.; Zhang, R.; Liu, Y.; Zhao, B.; Wu, Y.; Deng, J. Circularly polarized phosphorescence energy transfer combined with chirality-selective absorption for modulating full-color and white circularly polarized long afterglow. Angew. Chem. Int. Ed. 2024 , 63 , e202409514..

Wang, X.; Gao, X.; Zhong, H.; Yang, K.; Zhao, B.; Deng, J. Three-level chirality transfer and amplification in liquid crystal supramolecular assembly for achieving full-color and white circularly polarized luminescence. Adv. Mater. 2025 , 37 , e2412805..

Xu, L.; Wang, C.; Li, Y. X.; Xu, X. H.; Zhou, L.; L iu, N.; Wu, Z. Q. Crystallization-driven asymmetric helical assembly of conjugated block copolymers and the aggregation induced white-light emission and circularly polarized luminescence. Angew. Chem. Int. Ed. 2020 , 59 , 16675−16682..

Li, S. Y.; Duan, B. H.; Liu, N.; Luo, J.; Chen, Z.; Wu, Z. Q. Helical star-shaped bottlebrush polymers: from controlled synthesis to tunable photoluminescence and circularly polarized luminescence. ACS Macro Lett. 2024 , 13 , 1396−1402..

Guang, L.; Lu, Y.; Zhang, Y.; Liao, R.; Wang, F. Circularly polarized phosphorescence of benzils achieved by chiral supramolecular polymerization. Angew. Chem. Int. Ed. 2024 , 63 , e202315362..

[Freire, F.; Quiñoá, E.; Riguera, R., Supramolecular assemblies from poly(phenylacetylene)s. Chem. Rev . 2015, 116 , 1242−1271..

Wang, S.; Zhang, J.; Wan, X. Optically active helical poly(3,5-disubstituted phenylacetylene): conformation regulation, chirality transfer, and self-assembly. Acta Polymerica Sinica (in Chinese) 2021 , 52 , 898−911..

[Lam, J. W. Y.; Tang, B., Functional polyacetylenes. Acc. Chem. Res . 2005, 38 , 745−754..

Shi, L.; Zhu, X.; Sun, X.; Li, X.; Wang, S. Hydrogen bond-modulated conformational transition, chiral amplification, and self-assembly behavior of substituted poly(phenylacetylene)s. Macromolecules 2025 , 58 , 9098−9109..

Wang, S.; Sun, X.; Zeng, H.; Xie, S.; Zhang, J.; Wan, X. Postpolymerization modification-induced chiral self-assembly of substituted poly(phenylacetylene)s based on cis–transoid to cis–cisoid helical transition. Macromolecules 2025 , 58 , 1235−1244..

Shen, L.; Cao, Y.; Wang, L.; Zhang, X.; Zhang, A.; Li, W. Compressible hydrogels with stabilized chirality from thermoresponsive helical dendronized poly(phenylacetylene)s. Angew. Chem. Int. Ed. 2024 , 63 , e202407552..

Ren, L.; Lu, X.; Li, W.; Yan, J.; Whittaker, A. K.; Zhang, A. Thermoresponsive helical dendronized poly(phenylacetylene)s: remarkable stabilization of their helicity via photo-dimerization of the dendritic pendants. J. Am. Chem. Soc. 2023 , 145 , 24906−24921..

Freire, F.; Quinoa, E.; Riguera, R. Chiral nanostructure in polymers under different deposition conditions observed using atomic force microscopy of monolayers: poly(phenylacetylene)s as a case study. Chem. Commun. 2017 , 53 , 481−492..

Wang, S.; Feng, X.; Zhao, Z.; Zhang, J.; Wan, X. Reversible cis-cisoid to cis-transoid helical structure transition in poly(3,5-disubstituted phenylacetylene)s. Macromolecules 2016 , 49 , 8407−8417..

[Wang, S.; Shi, G.; Guan, X.; Zhang, J.; Wan, X. Cis-cisoid helical structures of poly(3,5-disubstituted phenylacetylene)s stabilized by intramolecular n → π* interactions. Macromolecules 2018, 51 , 1251-1259..

Wang, S.; Cai, S.; Zhang, J.; Wan, X. Tunable cis-cisoid helical conformation of poly(3,5-disubstibuted phenylacetylene)s stabilized by n→π* interaction. Chinese J. Polym. Sci. 2020 , 38 , 685−695..

Qiu, Y.; Zhang, Y.; Jiang, Q.; Wang, H.; Liao, Y.; Zhou, H.; Xie, X. Highly specif ic and sensitive naked-eye fluoride ion recognition via unzipping a helical poly(phenylacetylene). Macromolecules 2022 , 55 , 9057−9065..

Tarrio, J. J.; Rey-Tarrio, F.; Hermida, B.; Fernandez, B.; Crassous, J.; Quinoa, E.; Rodriguez, R.; Freire, F. Facial asymmetry in the helical grooves of chiral helical polymers to create 2D single-chain archimedean spiral nanostructures. ACS Nano 2025 , 19 , 33423−33429..

Fernandez-Miguez, M.; Quinoa, E.; Freire, F. Thermal activation of asymmetry amplification effects in helical polymer-metal complexes. Angew. Chem. Int. Ed. 2025 , 64 , e202503949..

Nunez-Martinez, M.; Fernandez-Miguez, M.; Quinoa, E.; Freire, F. Size control of chiral nanospheres obtained via nanoprecipitation of helical poly(phenylacetylene)s in the absence of surfactants. Angew. Chem. Int. Ed. 2024 , 63 , e202403313..

Rey-Tarrio, F.; Rodriguez, R.; Quinoa, E.; Freire, F. Screw sense excess and reversals of helical polymers in solution. Nat. Commun. 2023 , 14 , 1742..

Rodr iguez, R.; Quinoa, E.; Riguera, R.; Freire, F. Architecture of chiral poly(phenylacetylene)s: from compressed/highly dynamic to stretched/quasi-static helices. J. Am. Chem. Soc. 2016 , 138 , 9620−9628..

Wang, S.; Xie, S.; Zeng, H.; Du, H.; Zhang, J.; Wan, X. Self-reporting activated ester-amine reaction for enantioselective multi-channel visual detection of chiral amines. Angew. Chem. Int. Ed. 2022 , 61 , e202202268..

Wang, S.; Hu, D.; Guan, X.; Cai, S.; Shi, G.; Shuai, Z.; Zhang, J.; Peng, Q.; Wan, X. Brightening up circularly polarized luminescence of monosubstituted polyacetylene by conformation control: mechanism, switching, and sensing. Angew. Chem. Int. Ed. 2021 , 60 , 21918−21926..

Wang, S.; Xie, S.; Du, H.; Zeng, H.; Zhang, J.; Wan, X. Visualized thermoresponsive helix-helix switch of polyphenylacetylene with a wide-range tunable transition temperature. Sci. China Chem. 2023 , 66 , 887−895..

Wang, S.; Sun, X.; Zeng, H.; Zhang, J.; Wan, X. Fast Visualized conformational transition of polyphenylacetylenes with stepwise tunable circularly polarized luminescence. Chem. Eur. J. 2023 , 29 , e202301080..

Maeda, K.; Mochizuki, H.; Watanabe, M.; Yashima, E. Switching of macromolecular helicity of optically active poly(phenylacetylene)s bearing cyclodextrin pendants induced by various external stimuli. J. Am. Chem. Soc. 2006 , 128 , 7639−7650..

Shimomura, K.; Ikai, T.; Kanoh, S.; Yashima, E.; Maeda, K. Switchable enantioseparation based on macromolecular memory of a helical polyacetylene in the solid state. Nat. Chem. 2014 , 6 , 429−434..

Okuda, S.; Ikai, T.; Okutsu, H.; Ando, M.; Hattori, M.; Ishidate, R.; Yashima, E. Helix-sense-selective memory polymerization of biphenylylacetylenes bearing carboxy and amino groups in water. Angew. Chem. Int. Ed. 2024 , 63 , e202412752..

Han, J.; You, J.; Li, X.; Duan, P.; Liu, M. Full-color tunable circularly polarized luminescent nanoassemblies of achiral AIEgens in confined chiral nanotubes. Adv. Mater. 2017 , 29 , 1606503..

Han, X.; Bai, Q.; Yao, L.; Liu, H.; Gao, Y.; Li, J.; Liu, L.; Liu, Y.; Li, X.; Lu, P.; Yang, B. Highly efficient solid-state near-infrared emitting material based on triphenylamine and diphenylfumaron itrile with an EQE of 2.58% in nondoped organic light-emitting diode. Adv. Funct. Mater. 2015 , 25 , 7521−7529..

Wang, S.; Feng, X.; Zhang, J.; Yu, P.; Guo, Z.; Li, Z.; Wan, X. Helical conformations of poly(3,5-disubstituted phenylacetylene)s tuned by pendant structure and solvent. Macromolecules 2017 , 50 , 3489−3499..

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One-handed Helical Poly(m-terphenyl acetylene)s with Broad Optical Activity Range from Ultraviolet-Visible to Near-infrared Regions

One-handed Helical Poly(m-terphenyl acetylene)s with Broad Optical Activity Range from Ultraviolet-Visible to Near-infrared Regions

DOI：10.1007/s10118-026-3656-z

摘要

Abstract

关键词

Keywords

references