Multicomponent Polymerization of Diacetylarenes, Dialkynones, and NH<sub>4</sub>OAc for <italic style="font-style: italic">In situ</italic> Construction of Functional Conjugated Poly(triarylpyridine)s

Shi-Han Yu; Lu Wang; Meng-Chao Zhang; Hong-Kun Li

doi:10.1007/s10118-025-3362-2

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Multicomponent Polymerization of Diacetylarenes, Dialkynones, and NH₄OAc for In situ Construction of Functional Conjugated Poly(triarylpyridine)s

RESEARCH ARTICLE | Updated：2025-08-25

- Multicomponent Polymerization of Diacetylarenes, Dialkynones, and NH₄OAc for In situ Construction of Functional Conjugated Poly(triarylpyridine)s
- Chinese Journal of Polymer Science Vol. 43, Issue 9, Pages: 1496-1504(2025)
- Affiliations：
  
  Laboratory of Advanced Optoelectronic Materials, Suzhou Key Laboratory of Novel Semiconductor-Optoelectronics Materials and Devices, State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, Jiangsu Engineering Laboratory of Novel Functional Polymeric Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
- Author bio：
  
  hkli@suda.edu.cn
- Funds：
- DOI：10.1007/s10118-025-3362-2
  CLC：
- Received：15 March 2025，
  
  Revised：2025-04-12，
  
  Accepted：17 April 2025，
  
  Online First：03 July 2025，
  
  Published：05 September 2025
- Accepted：
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Yu, S. H.; Wang, L.; Zhang, M. C.; Li, H. K. Multicomponent polymerization of diacetylarenes, dialkynones, and NH₄OAc for in situ construction of functional conjugated poly(triarylpyridine)s. Chinese J. Polym. Sci. 2025, 43, 1496–1504 DOI: 10.1007/s10118-025-3362-2.

Shi-Han Yu, Lu Wang, Meng-Chao Zhang, et al. Multicomponent Polymerization of Diacetylarenes, Dialkynones, and NH₄OAc for In situ Construction of Functional Conjugated Poly(triarylpyridine)s[J]. Chinese Journal of Polymer Science, 2025, 43(9): 1496-1504. DOI: 10.1007/s10118-025-3362-2.
Yu, S. H.; Wang, L.; Zhang, M. C.; Li, H. K. Multicomponent polymerization of diacetylarenes, dialkynones, and NH₄OAc for in situ construction of functional conjugated poly(triarylpyridine)s. Chinese J. Polym. Sci. 2025, 43, 1496–1504 DOI: 10.1007/s10118-025-3362-2. DOI：

Shi-Han Yu, Lu Wang, Meng-Chao Zhang, et al. Multicomponent Polymerization of Diacetylarenes, Dialkynones, and NH₄OAc for In situ Construction of Functional Conjugated Poly(triarylpyridine)s[J]. Chinese Journal of Polymer Science, 2025, 43(9): 1496-1504. DOI: 10.1007/s10118-025-3362-2. DOI：

摘要

The multicomponent polymerization of acetylarene

alkynones and NH

OAc is developed for

in-situ

construction of soluble conjugated poly(triarylpyridine)s with aggregation-induced emission and room-temperature phosphorescence characteristics.

Abstract

Exploration of new green polymerization strategies for the construction of conjugated polymers is important but challengeable. In this work

a multicomponent polymerization of acetylarenes

alkynones and ammonium acetate for

in situ

construction of conjugated poly(triarylpyridine)s was developed. The polymerization reactions of diacetylarenes

aromatic dialkynones and NH

OAc were performed in dimethylsulfoxide (DMSO) under heating in the presence of potassium

tert

-butoxide (

-BuOK)

affording four conjugated poly(2

6-triarylpyridine)s (PTAPs) in satisfactory yields. The resulting PTAPs have good solubility in common organic solvents and high thermal stability with 5% weight loss temperatures reaching up to 460 °C. They are also electrochemically active. The PTAPs incorporating tetraphenylethene units manifest aggregation-induced emission features. Moreover

through simply being doped into poly(vinyl alcohol) (PVA) matrix

the polymer and model compound containing triphenylamine moieties exhibit room-temperature phosphorescence properties wi

th ultralong lifetimes up to 696.2 ms and high quantum yields up to 28.7%. This work not only provides a facile green synthetic route for conjugated polymers but also offers new insights into the design of advanced materials with unique photophysical properties.

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references

Wang, Y.; Feng, L.; Wang, S. Conjugated polymer nanoparticles for imaging, cell activity regulation, and therapy. Adv. Funct. Mater. 2019 , 29 , 1806818..

Xu, M.; Wei, C.; Zhang, Y.; Chen, J.; Li, H.; Zhang, J.; Sun, L.; Liu, B.; Lin, J.; Yu, M.; Xie, L.; Huang, W. Coplanar conformational structure of π -conjugated polymers for optoelectronic applications. Adv. Mater. 2024 , 36 , 2301671..

Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Light-emitting diodes based on conjugated polymers. Nature 1990 , 347 , 539−541..

Cheng, Y. J.; Yang, S. H.; Hsu, C. S. Synthesis of conjugated polymers for organic solar cell applications. Chem. Rev. 2009 , 109 , 5868−5923..

Kimpel, J.; Michinobu, T. Conjugated polymers for functional applications: lifetime and performance of polymeric organic semiconductors in organic field-effect transistors. Polym. Int. 2021 , 70 , 367−373..

Li, Y. F.; Guo, Y. L.; Liu, Y. Q. Recent progress in donor acceptor type conjugated polymers for organic field-effect transistors. Chinese J. Polym. Sci. 2023 , 41 , 652−670..

Ding, L.; Yu, Z. D.; Wang, X. Y.; Yao, Z. F.; Lu, Y.; Yang, C. Y.; Wang, J. Y.; Pei, J. Polymer semiconductors: synthesis, processing, and applications. Chem. Rev. 2023 , 123 , 7421−7497..

Sobhanan, J.; Jones, P.; Kohara, R.; Sugino, S.; Vacha, M.; Subrahmanyam, C.; Takano, Y.; Lacy, F.; Biju, V. Toxicity of nanomaterials due to photochemical degradation and the releaseof heavy metal ions. Nanoscale 2020 , 12 , 22049−22058..

Usluer, Ö.; Abbas, M.; Wantz, G.; Vignau, L.; Hirsch, L.; Grana, E.; Brochon, C.; Cloutet, E.; Hadziioannou, G. Metal residues in semiconducting polymers: impact on the performance of organic electronic devices. ACS Macro Lett. 2014 , 3 , 1134−1138..

Ye, S.; Lotocki, V.; Xu, H.; Seferos, D. S. Group 16 conjugated polymers based on furan, thiophene, selenophene, and tellurophene. Chem. Soc. Rev. 2022 , 51 , 6442−6474..

Koga, T.; Nabae, Y.; Funakawa, A.; Hayakawa, T.; Kakimoto, M. Synthesis of hyperbranched polypyridine via a cross coupling approach as an n-type π -conjugated polymer. Macromol. Chem. Phys. 2017 , 218 , 1700391..

Nanashima, Y.; Yokoyama, A.; Yokozawa, T. Synthesis of novel blue-light-emitting polypyridine. J. Polym. Sci., Part A: Polym. Chem. 2012 , 50 , 1054−1061..

Kotnik, T.; Kovačič, S. Modern methods for conjugated polymers preparation: a concept of transition metal-free synthesis. Eur. J. Org. Chem. 2025 , 28 , e202400874..

Liu, Y.; Lam, J. W. Y.; Tang, B. Z. Conjugated polymers developed from alkynes. Natl. Sci. Rev. 2015 , 2 , 493−509..

Bunz, U. H. F.; Seehafer, K.; Geyer, F. L.; Bender, M.; Braun, I.; Sm arsly, E.; Freudenberg, J. Porous polymers based on aryleneethynylene building blocks. Macromol. Rapid Commun. 2014 , 35 , 1466−1496..

Hu, R.; Li, W.; Tang, B. Z. Recent advances in alkyne-based multicomponent polymerizations. Macromol. Chem. Phys. 2016 , 217 , 213−224..

Liu, Y.; Qin, A.; Tang, B. Z. Polymerizations based on triple-bond building blocks. Prog. Polym. Sci. 2018 , 78 , 92−138..

Yang, F.; Zhang, Z.; Chen, M.; Zhang, H.; Zhang, J.; Sun, J. Z. Functional polydiynes prepared by metathesis cyclopolymerization of 1,7-dihalogen-1,6-heptadiyne derivatives. Polym. Chem. 2022 , 13 , 6492−6499..

Wang, L.; Zhan, Y.; Zhang, L.; Li, H. Metal-free polycyclotrimerization of trimethylsilyl-protected diynes: a facile strategy toward regioregular hyperbranched polyarylenes. Polym. Chem. 2023 , 14 , 2878−2887..

Fu, X.; Qin, A.; Tang, B. Z. X-yne click polymerization. Aggregate 2023 , 4 , e350..

Huo, X.; Li, H.; Li, Y. Synthesis of a conjugated polytetraarylethene with aggregation-enhanced emission by palladium-catalyzed internal alkyne-based multicomponent polymerization. Mater. Lett. 2023 , 345 , 134492..

He, B.; Huang, J.; Liu, X.; Zhang, J.; Lam, J. W. Y.; Tang, B. Z. Polymerizations of activated alkynes. Prog. Polym. Sci. 2022 , 126 , 101503..

Zhao, E.; Li, H.; Ling, J.; Wu, H.; Wang, J.; Zhang, S.; Lam, J. W. Y.; Sun, J. Z.; Qin, A.; Tang, B. Z. Structure-dependent emission of polytriazoles. Polym. Chem. 2014 , 5 , 2301−2308..

Marrocchi, A.; Facchetti, A.; Lanari, D.; Santoro, S.; Vaccaro, L. Click-chemistry approaches to π -conjugated polymers for organic electronics applications. Chem. Sci. 2016 , 7 , 6298−6308..

Fu, W.; Dong, L.; Shi, J.; Tong, B.; Cai, Z.; Zhi, J.; Dong, Y. Synthesis of polyquinolines via one-pot polymerization of alkyne, aldehyde, and aniline under metal-free catalysis and their properties. Macromolecules 2018 , 51 , 3254−3263..

Deng, H.; Hu, R.; Zhao, E.; Chan, C. Y. K.; Lam, J. W. Y.; Tang, B. Z. One-pot three-component tandem polymerization toward functional poly(arylene thiophenylene) with aggregation-enhanced emission characteristics. Macromolecules 2014 , 47 , 4920−4929..

Kayser, L. V.; Vollmer, M.; Welnhofer, M.; Krikcziokat, H.; Meerholz, K.; Arndtsen, B. A. Metal-free, multicomponent synthesis of pyrrole-based π -conjugated polymers from imines, acid chlorides, and alkynes. J. Am. Chem. Soc. 2016 , 138 , 10516−10521..

Tang, X.; Zheng, C.; Chen, Y.; Zhao, Z.; Qin, A.; Hu, R.; Tang, B. Z. Multicomponent tandem polymerizations of aromatic diynes, terephthaloyl chloride, and hydrazines toward functional conjugated polypyrazoles. Macromolecules 2016 , 49 , 9291−9300..

Shabalin, D. A.; Dvorko, M. Y.; Schmidt, E. Y.; Trofimov, B. A. Regiocontrolled synthesis of 2,4,6-triarylpyridines from methyl ketones, electron-deficient acetylenes and ammonium acetate. Org. Biomol. Chem. 2021 , 19 , 2703−2715..

Peng, J.; Tian, T.; Xu, S.; Hu, R.; Tang, B. Z. Base-assisted polymerizations of elemental sulfur and alkynones for temperature-controlled synthesis of polythiophenes or poly(1,4-dithiin)s. J. Am. Chem. Soc. 2023 , 145 , 28204−28215..

Österholm, A. M.; Ponder, J. F. Jr.; De Keersmaecker, M.; Shen, D. E.; Reynolds, J. R. Disentangling redox properties and capacitance in solution-processed conjugated polymers. Chem. Mater. 2019 , 31 , 2971−2982..

Wang, P.; Lin, S.; Lin, Z.; Peeks, M. D.; Van Voorhis, T.; Swager, T. M. A semiconducting conjugated radical polymer: ambipolar redox activity and faraday effect. J. Am. Chem. Soc. 2018 , 140 , 10881−10889..

[Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Aggregation-induced emission: together we shine, united we soar! Chem. Rev . 2015 , 115 , 11718–11940..

Long, Z.; Mao, L.; Liu, M.; Wan, Q.; Wan, Y.; Zhang, X.; Wei, Y. Marrying multicomponent reactions and aggregation-induced emission (AIE): new directions for fluorescent nanoprobes. Polym. Chem. 2017 , 8 , 5644−5654..

Li, H.; Li, B. S.; Tang, B. Z. Molecular design, circularly polarized luminescence, and helical self-assembly of chiral aggregation-induced emission molecules. Chem. Asian J. 2019 , 14 , 674−688..

Cai, X.; Liu, B. Aggregation-induced emission: recent advances in materials and biomedical applications. Angew. Chem. Int. Ed. 2020 , 59 , 9868−9886..

Wang, F.; Ho, P. Y.; Kam, C.; Yang, Q.; Liu, J.; Wang, W.; Zhao, E.; Chen, S. An AIE-active probe for efficient detection and high-throughput identification of outer membrane vesicles. Aggregate 2023 , 4 , e312..

Duo, Y.; Han, L.; Yang, Y.; Wang, Z.;Wang, L.; Chen, J.; Xiang, Z.; Yoon, J.; Luo, G.; Tang, B. Z. Aggregation-induced emission luminogen: role in biopsy for precision medicine. Chem. Rev. 2024 , 124 , 11242−11347..

Yuan, S.; Zhao, E. Recent advances of lipid droplet-targeted AIE-active materials for imaging, diagnosis and therapy. Biosens. Bioelectron. 2025 , 267 , 116802..

Hu, R.; Leung, N. L. C.; Tang, B. Z. AIE macromolecules: syntheses, structures and functionalities. Chem. Soc. Rev. 2014 , 43 , 4494−4562..

Jiang, Y.; Hadjichristidis, N. Tetraphenylethene-functionalized polyethylene-based polymers with aggregation-induced emission. Macromolecules 2019 , 52 , 1955−1964..

Hu, R.; Qin, A.; Tang, B. Z. AIE polymers: Synthesis and applications. Prog. Polym. Sci. 2020 , 100 , 101176..

Du, J.; Huang, D.; Li, H.; Qin, A.; Tang, B. Z.; Li, Y. Catalyst-free click polymerization of thiol and activated internal alkynes: a facile strategy toward functional poly( β -thioacrylate)s. Macromolecules 2020 , 53 , 4932−4941..

Sánchez-Ruiz, A.; Sousa-Hervés, A.; Tolosa Barrilero, J.; Navarro, A.; Garcia-Martinez, J. C. Aggregation-induced emission properties in fully π-conjugated polymers, dendrimers, and oligomers. Polymers 2021 , 13 , 213..

Fang, H.; Huo, X.; Wang, L.; Si,H.; Li, H.; Qin, A.; Tang, B. Z.; Li, Y. Rhodium-c atalyzed polycyclotrimerization of diphenylpropiolates: a facile strategy toward ester-functionalized hyperbranched polyarylenes. Macromolecules 2022 , 55 , 2456−2462..

[Jia, H.; Xu, N.; Nagai, Y.; Doi, M.; Sawada, T.; Serizawa, T.; Ando, S.; Habuchi, S.; Michinobu, T. Controlling AIE and ACQ properties of conjugated carbazole-tetraphenylethene copolymers by ethynylene spacer. Polym. Chem . 2023 , 14 , 2510–2519..

Han, X.; Tong, J.; Ding, G.; Sun, C.; Wang, X.; Su, Z.; Sun, J.; Wen, L.-L.; Shan, G.-G. Highly emissive coordination polymer derived from tetraphenylethylene-tetrazole chromophore: synthesis, characterization and piezochromic luminescent behavior. Chin. Chem. Lett. 2023 , 34 , 107255..

Shi, F.; Zhang, W.; Zhang, J.; Li, H.; Shi, Li. B. Tetraphenylethylene-based conjugated polymers with valine-containing side chains: Aggregation-induced emission, helical self-assembly, complexation-induced circularly polarized luminescence. Eur. Polym. J. 2024 , 218 , 113342..

Liu, X.; Gao, R.; Wang, Q.; Wang, L.; Yang, W. Thermoresponsive AIE-active miktoarm star polymers: precise synthesis and structure-dependent photoluminescence. Macromolecules 2025 , 58 , 1126−1142..

Gan, N.; Shi, H.; An, Z.; Huang, W. Recent advances in polymer-based metal-free room-temperature phosphorescent materials. Adv. Funct. Mater. 2018 , 28 , 1802657..

Wang, J.; Lou, X.-Y.; Wang, Y.; Tang, J.; Yang, Y.-W. Recent advances of polymer-based pure organic room temperature phosphorescent materials. Macromol. Rapid Commun. 2021 , 42 , 2100021..

Zhang, Y.; Su, Y.; Wu, H.; Wang, Z.; Wang, C.; Zheng, Y.; Zheng, X.; Gao, L.; Zhou, Q.; Yang, Y.; Chen, X.; Yang, C.; Zhao, Y. Large-area, flexible, transparent, and long-lived polymer-based phosphorescence films. J. Am. Chem. Soc. 2021 , 143 , 13675−13685..

Gong, Y.; Yang, J.; Fang, M.; Li, Z. Room-temperature phosphorescence from metal-free polymer-based materials. Cell Rep. Phys. Sci. 2022 , 3 , 100663..

Liu, Z.; Fan, C.; Yuan, Y.; Zhang, H. Synthesis and properties of long-lived room-temperature phosphorescent liquid crystal polymers based on “Jacketing” effect. Eur. Polym. J. 2024 , 202 , 112611..

Qiu, L.; Chen, Z.; Wu, J.; Zeng, G.; Liu, X.; Liu, K.; Su, S.-j.; Loos, J.; Wen, T. Room-temperature phosphorescence induced by heterogeneous polymer matrixes. Macromolecules 2024 , 57 , 2679−2686..

Dou, X.; Wang, X.; Xie, X.; Zhang, J.; Li, Y.; Tang, B. Advances in polymer-based organic room-temperature phosphorescence materials. Adv. Funct. Mater. 2024 , 34 , 2314069..

Huang, J.; Qu, L.; Gao, L.; Wang, X.; Chen, Q.; Wang, Y.; Zhu, Y.; Li, C.; Li, Y.; Yang, C. Multicolor room-temperature phosphorescence achieved by intrinsic polymers containing solely one phosphor unit. Macromolecules 2024 , 57 , 5018−5027..

Xiong, S.; Xiong, Y.; Wang, D.; Pan, Y.; Chen, K.; Zhao, Z.; Wang, D.; Tang, B. Z. Achieving tunable organic afterglow and UV-irradiation-responsive ultralong room-temperature phosphorescence from pyridine-substituted triphenylamine derivatives. Adv. Mater. 2023 , 35 , 2301874..

Zhang, Z. Y.; Deng, C. Y.; Shen, C. C.; Xu, R. Y.; Wang, X. Z.; Wang, Y. H; Ding, B.; Li, B.; Li, J.; Li, C. Phosphorescence enhancement of pyridinium macrocycles by poly(vinylalcohol). Chem. Commun. 2023 , 59 , 11248−11251..

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Multicomponent Polymerization of Diacetylarenes, Dialkynones, and NH4OAc for In situ Construction of Functional Conjugated Poly(triarylpyridine)s

DOI：10.1007/s10118-025-3362-2

摘要

Abstract

关键词

Keywords

references

Multicomponent Polymerization of Diacetylarenes, Dialkynones, and NH₄OAc for In situ Construction of Functional Conjugated Poly(triarylpyridine)s