Synthesis of Functional Hyperbranched Poly(methyltriazolylcarboxylate)s by Catalyst-free Click Polymerization of Butynoates and Azides

Mu-Ning Lang; Wei-Wen Chi; Ting Han; Qing-Zhen Zhao; Hong-Kun Li; Ben Zhong Tang; Yong-Fang Li

doi:10.1007/s10118-020-2421-y

Your Location：

Home >

Browse articles >

Synthesis of Functional Hyperbranched Poly(methyltriazolylcarboxylate)s by Catalyst-free Click Polymerization of Butynoates and Azides

ARTICLE | Updated：2020-05-25

- Synthesis of Functional Hyperbranched Poly(methyltriazolylcarboxylate)s by Catalyst-free Click Polymerization of Butynoates and Azides
- Synthesis of Functional Hyperbranched Poly(methyltriazolylcarboxylate)s by Catalyst-free Click Polymerization of Butynoates and Azides
- Chinese Journal of Polymer Science 2020年38卷第11期页码：1171-1177
- Affiliations：
  
  a.State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, Laboratory of Advanced Optoelectronic Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
  b.State Key Laboratory of Luminescent Materials and Devices, Key Laboratory of Luminescence from Molecular Aggregates of Guangdong Province, Center for Aggregation-Induced Emission, South China University of Technology, Guangzhou 510640, China
  c.Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China
- Author bio：
  
  hkli@suda.edu.cn
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (Nos. 21875152 and 21404077), the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 17KJB150034), the Open Fund of Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, Guangzhou 510640, China (South China University of Technology) (No. 2019B030301003), and the Priority Academic Program Development of Jiangsu High Education Institutions (PAPD). M. N. L. and Q. Z. Z. thank the financial support from Undergraduate Training Program for Innovation and Entrepreneurship, Soochow University (No. 2018xj032). H. K. L. acknowledges the supports from Jiangsu Planned Projects for Postdoctoral Research Funds (No. 1501023B) and China Postdoctoral Science Foundation (No. 2016M591906).
- DOI：10.1007/s10118-020-2421-y
  中图分类号：
- 收稿：2020-02-24，
  
  修回：2020-3-10，
  
  录用：2020-3-11，
  
  网络首发：2020-05-25，
  
  纸质出版：2020-08-14
- Accepted：
Scan QR Code
Lang, M. N.; Chi, W. W.; Han, T.; Zhao, Q. Z.; Li, H. K.; Tang, B. Z.; Li, Y. F. Synthesis of functional hyperbranched poly(methyltriazolylcarboxylate)s by catalyst-free click polymerization of butynoates and azides. Chinese J. Polym. Sci. 2020, 38, 1171–1177

Mu-Ning Lang, Wei-Wen Chi, Ting Han, et al. Synthesis of Functional Hyperbranched Poly(methyltriazolylcarboxylate)s by Catalyst-free Click Polymerization of Butynoates and Azides[J]. Chinese Journal of Polymer Science, 2020, 38(11): 1171-1177.
Lang, M. N.; Chi, W. W.; Han, T.; Zhao, Q. Z.; Li, H. K.; Tang, B. Z.; Li, Y. F. Synthesis of functional hyperbranched poly(methyltriazolylcarboxylate)s by catalyst-free click polymerization of butynoates and azides. Chinese J. Polym. Sci. 2020, 38, 1171–1177 DOI： 10.1007/s10118-020-2421-y.

Mu-Ning Lang, Wei-Wen Chi, Ting Han, et al. Synthesis of Functional Hyperbranched Poly(methyltriazolylcarboxylate)s by Catalyst-free Click Polymerization of Butynoates and Azides[J]. Chinese Journal of Polymer Science, 2020, 38(11): 1171-1177. DOI： 10.1007/s10118-020-2421-y.

摘要

Abstract

Azide-alkyne click polymerization has become a powerful tool for polymer synthesis. However

the click polymerization between internal alkynes and azides is rarely utilized to prepare functional polymers. In this work

the polymerization reactions of activated internal alkyne monomers of tris(2-butynoate)s (

) with tetraphenylethene-containing diazides (

) were performed in dimethylformamide (DMF) under simple heating

affording four hyperbranched poly(methyltriazolylcarboxylate)s (

-PMTCs) with high molecular weights (

up to 2.4 × 10

) and regioregularities (up to 83.9%) in good yields. The

-PMTCs are soluble in common organic solvents

and thermally stable with 5% weight loss temperatures up to 400 °C. They are non-emissive in dilute solution

but become highly emissive in aggregated state

exhibiting aggregation-induced emission characteristics. The polymers can generate fluorescent photopatterns with high resolution

and can work as fluorescent sensors to detect nitroaromatic explosive with high sensitivity.

关键词

Keywords

references

Yan, D.; Gao, C.; Frey, H. Hyperbranched polymers , John Wiley & amp; Sons, Inc., Hoboken, NJ, 2011 .

Voit, B. I.; Lederer, A. . Hyperbranched and highly branched polymer architectures—synthetic strategies and major characterization aspects . Chem. Rev. , 2009 . 109 5924 - 5973 . DOI: 10.1021/cr900068q http://doi.org/10.1021/cr900068q .

Dong, Z.; Ye, Z. . Hyperbranched polyethylenes by chain walking polymerization: synthesis, properties, functionalization, and applications . Polym. Chem. , 2012 . 3 286 - 30 . DOI: 10.1039/C1PY00368B http://doi.org/10.1039/C1PY00368B .

Žagar, E.; Žigon, M. . Aliphatic hyperbranched polyesters based on 2,2-bis(methylol)propionic acid—determination of structure, solution and bulk properties . Prog. Polym. Sci. , 2011 . 36 53 - 88 . DOI: 10.1016/j.progpolymsci.2010.08.004 http://doi.org/10.1016/j.progpolymsci.2010.08.004 .

Abbina, S.; Vappala, S.; Kumar, P.; Siren, E. M. J.; La, C. C.; Abbasi, U.; Brooks, D. E.; Kizhakkedathu, J. H. . Hyperbranched polyglycerols: recent advances in synthesis, biocompatibility and biomedical applications . J. Mater. Chem. B , 2017 . 5 9249 - 9277 . DOI: 10.1039/C7TB02515G http://doi.org/10.1039/C7TB02515G .

Yang, M. L.; Wu, Y. X.; Liu, Y.; Qiu, J. J.; Liu, C. M. . A novel bio-based AB 2 monomer for preparing hyperbranched polyamides derived from levulinic acid and furfurylamine . Polym. Chem. , 2019 . 10 6217 - 6226 . DOI: 10.1039/C9PY01253B http://doi.org/10.1039/C9PY01253B .

Hammer, B. A. G.; Müllen, K. . Dimensional evolution of polyphenylenes: expanding in all directions . Chem. Rev. , 2016 . 116 2103 - 2140 . DOI: 10.1021/acs.chemrev.5b00515 http://doi.org/10.1021/acs.chemrev.5b00515 .

Liu, J.; Huang, W.; Pang, Y.; Yan, D. . Hyperbranched polyphosphates: synthesis, functionalization and biomedical applications . Chem. Soc. Rev. , 2015 . 44 3942 - 3953 . DOI: 10.1039/C5CS00318K http://doi.org/10.1039/C5CS00318K .

Bej, R . Hyperbranched polydisulfides . Polym. Chem. , 2020 . 11 990 - 1000 . DOI: 10.1039/C9PY01675A http://doi.org/10.1039/C9PY01675A .

Chen, H.; Kong, J. . Hyperbranched polymers from A 2 + B 3 strategy: recent advances in description and control of fine topology . Polym. Chem. , 2016 . 7 3643 - 3663 . DOI: 10.1039/C6PY00409A http://doi.org/10.1039/C6PY00409A .

Zheng, Y.; Li, S.; Weng, Z.; Gao, C. . Hyperbranched polymers: advances from synthesis to applications . Chem. Soc. Rev. , 2015 . 44 4091 - 4130 . DOI: 10.1039/C4CS00528G http://doi.org/10.1039/C4CS00528G .

Wu, W.; Tang, R.; Li, Q.; Li, Z. . Functional hyperbranched polymers with advanced optical, electrical and magnetic properties . Chem. Soc. Rev. , 2015 . 44 3997 - 4022 . DOI: 10.1039/C4CS00224E http://doi.org/10.1039/C4CS00224E .

Liu, J.; Lam, J. W. Y.; Tang, B. Z. . Acetylenic polymers: syntheses, structures, and functions . Chem. Rev. , 2009 . 109 5799 - 5807 . DOI: 10.1021/cr900149d http://doi.org/10.1021/cr900149d .

Liu, Y.; Qin, A.; Tang, B. Z. . Polymerizations based on triple-bond building blocks . Prog. Polym. Sci. , 2018 . 78 92 - 138 . DOI: 10.1016/j.progpolymsci.2017.09.004 http://doi.org/10.1016/j.progpolymsci.2017.09.004 .

Huang, D.; Qin, A.; Tang, B. Z. . Hyperbranched polymers prepared by alkyne-based click polymerization . Acta Polymerica Sinica (in Chinese) , 2017 . 178 - 199 . .

Huang, D.; Liu, Y.; Qin, A.; Tang, B. Z. . Recent advances in alkyne-based click polymerizations . Polym. Chem. , 2018 . 9 2853 - 2867 . DOI: 10.1039/C7PY02047C http://doi.org/10.1039/C7PY02047C .

Shi, Y.; Cao, X.; Zou, L.; Gan, W.; Gao, H. . Preparation of water-soluble hyperbranched polymers with tunable thermosensitivity using chain-growth CuAAC copolymerization . Polym. Chem. , 2016 . 7 7500 - 7505 . DOI: 10.1039/C6PY01712F http://doi.org/10.1039/C6PY01712F .

Qin, A.; Lam, J. W. Y.; Tang, B. Z . Click polymerization . Chem. Soc. Rev. , 2010 . 39 2522 - 2544 . DOI: 10.1039/b909064a http://doi.org/10.1039/b909064a .

Scheel, A. J.; Komber, H.; Voit, B. . Novel hyperbranched poly([1,2,3]-triazole)s derived from AB 2 Monomers by a 1,3-dipolar cycloaddition. Macromol . Macromol. Rapid Commun. , 2004 . 25 1175 - 1180 . DOI: 10.1002/marc.200400097 http://doi.org/10.1002/marc.200400097 .

Li, B.; Huang, D.; Qin, A.; Tang, B. Z. . Progress on catalytic systems used in click polymerization . Macromol. Rapid Commun. , 2018 . 39 1800098 DOI: 10.1002/marc.201800098 http://doi.org/10.1002/marc.201800098 .

Wu, J.; Chen, J.; Wang, J.; Liao, X.; Xie, M.; Sun, R. . Synthesis and conductivity of hyperbranched poly(triazolium)s with various end-capping groups . Polym. Chem. , 2016 . 7 633 - 642 . DOI: 10.1039/C5PY01735A http://doi.org/10.1039/C5PY01735A .

Tang, R.; Chen, H.; Zhou, S.; Xiang, W.; Tang, X.; Liu, B.; Dong, Y.; Zeng, H.; Li, Z. . Dendronized hyperbranched polymers containing isolation chromophores: design, synthesis and further enhancement of the comprehensive NLO performance . Polym. Chem. , 2015 . 6 5580 - 5589 . DOI: 10.1039/C5PY00155B http://doi.org/10.1039/C5PY00155B .

Wang, X.; Hu, R.; Zhao, Z.; Qin, A.; Tang, B. Z. . Self-healing hyperbranched polytriazoles prepared by metal-free click polymerization of propiolate and azide monomers . Sci. China: Chem. , 2016 . 59 1554 - 1560 . .

Qin, A.; Liu, Y.; Tang, B. Z. . Regioselective metal-free click polymerization of azides and alkynes . Macromol. Chem. Phys. , 2015 . 216 818 - 828 . DOI: 10.1002/macp.201400571 http://doi.org/10.1002/macp.201400571 .

Sandmannn, B.; Happ, B.; Vitz, J.; Paulus, R. M.; Hager, M. D.; Burtscher, P.; Moszner, N.; Schubert, U. S. . Metal-free cycloaddition of internal alkynes and multifunctional azides under solvent-free conditions . Macromol. Chem. Phys. , 2014 . 215 1603 - 1608 . DOI: 10.1002/macp.201400149 http://doi.org/10.1002/macp.201400149 .

Pretzel, D.; Sandmann, B.; Hartlieb, M.; Vitz, J.; Hölzer, S.; Fritz, N.; Moszner, N.; Schubert, U. S. . Biological evaluation of 1,2,3-triazole-based polymers for potential applications as hard tissue material . J. Polym. Sci., Part A: Polym. Chem. , 2015 . 53 1843 - 1847 . DOI: 10.1002/pola.27676 http://doi.org/10.1002/pola.27676 .

Yuan, W.; Chi, W.; Han, T.; Du, J.; Li, H.; Li, Y.; Tang, B. Z. . Metal-free phenylpropiolate-azide polycycloaddition: efficient synthesis of functional poly(phenyltriazolylcarboxylate)s . Polym. Chem. , 2018 . 9 5215 - 5223 . DOI: 10.1039/C8PY01041B http://doi.org/10.1039/C8PY01041B .

Chi, W.; Yuan, W.; Du, J.; Han, T.; Li, H.; Li, Y.; Tang, B. Z. . Construction of functional hyperbranched poly(phenyltriazolylcarboxylate)s by metal-free phenylpropiolate-azide polycycloaddition . Macromol. Rapid Commun. , 2018 . 39 1800604 DOI: 10.1002/marc.201800604 http://doi.org/10.1002/marc.201800604 .

Du, J.; Yuan, W.; Zhang. H.; Li, H.; Li, Y.; Tang, B. Z. . Ferrocene-based hyperbranched poly(phenyltriazolylcarboxylate)s: synthesis by phenylpropiolate-azide polycycloaddition and use as precursors to nanostructured magnetoceramics . Polym. Chem. , 2019 . 10 5931 - 5938 . DOI: 10.1039/C9PY01375J http://doi.org/10.1039/C9PY01375J .

Chi, W. W.; Zhang, R. Y.; Han, T.; Du, J.; Li, H. K.; Zhang, W. J.; Li, Y. F.; Tang, B. Z. . Facile synthesis of functional poly(methyltriazolylcarboxylate)s by solvent- and catalyst-free butynoate-azide polycycloaddition . Chinese J. Polym. Sci. , 2020 . 38 17 - 23 . DOI: 10.1007/s10118-019-2316-y http://doi.org/10.1007/s10118-019-2316-y .

Muchtar, Z.; Schappacher, M.; Deffieux, A. . Hyperbranched nanomolecules: regular polystyrene dendrigrafts . Macromolecules , 2001 . 34 7595 - 7600 . DOI: 10.1021/ma010429q http://doi.org/10.1021/ma010429q .

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 . DOI: 10.1021/acs.chemrev.5b00263 http://doi.org/10.1021/acs.chemrev.5b00263 .

Zhou, S. Y.; Wan, H. B.; Zhou, F.; Gu, P. Y.; Xu, Q. F.; Lu, J. M. . AIEgens-lightened functional polymers: synthesis, properties and applications . Chinese J. Polym. Sci. , 2019 . 37 302 - 326 . DOI: 10.1007/s10118-019-2217-0 http://doi.org/10.1007/s10118-019-2217-0 .

Feng, G.; Liu, B. . Aggregation-induced emission (AIE) dots: emerging theranostic nanolights . Acc. Chem. Res. , 2018 . 51 1404 - 1414 . DOI: 10.1021/acs.accounts.8b00060 http://doi.org/10.1021/acs.accounts.8b00060 .

Yang, Z.; Chi, Z.; Mao, Z.; Zhang, Y.; Liu, S.; Zhao, J.; Aldred, M. P.; Chi, Z. . Recent advances in mechano-responsive luminescence of tetraphenylethylene derivatives with aggregation-induced emission properties . Mater. Chem. Front. , 2018 . 2 861 - 890 . DOI: 10.1039/C8QM00062J http://doi.org/10.1039/C8QM00062J .

Ma, S.; Ma, L.; Han, W.; Jiang, S.; Xu, B.; Tian, W. . Progress in 9,10-distyrylanthracene derivatives with aggregation-induced emission . Sci. Sin. Chim. , 2018 . 48 683 - 697 . DOI: 10.1360/N032018-00009 http://doi.org/10.1360/N032018-00009 .

Hu, Y. B.; Lam, J. W. Y.; Tang, B. Z. . Recent progress in AIE-active polymers . Chinese J. Polym. Sci. , 2019 . 37 289 - 301 . DOI: 10.1007/s10118-019-2221-4 http://doi.org/10.1007/s10118-019-2221-4 .

Xie, Y.; Gong, Y.; Han, M.; Zhang, F.; Peng, Q.; Xie, G.; Li, Z. . Tetraphenylcyclopentadiene-based hyperbranched polymers: convenient syntheses from one pot “A 4 + B 2 ” polymerization and high external quantum yields up to 9.74% in OLED devices . Macromolecules , 2019 . 52 896 DOI: 10.1021/acs.macromol.8b02051 http://doi.org/10.1021/acs.macromol.8b02051 .

Huang, Y.; Chen, P.; Wei, B.; Hu, R.; Tang, B. Z. . Aggregation-induced emission-active hyperbranched poly(tetrahydropyrimidine)s synthesized from multicomponent tandem polymerization . Chinese J. Polym. Sci. , 2019 . 37 428 - 436 . DOI: 10.1007/s10118-019-2230-3 http://doi.org/10.1007/s10118-019-2230-3 .

Wang, J.; Mei, J.; Yuan, W.; Lu, P.; Qin, A.; Sun, J.; Ma, Y.; Tang, B. Z. . Hyperbranched polytriazoles with high molecular compressibility: aggregation-induced emission and superamplified explosive detection . J. Mater. Chem. , 2011 . 21 4056 - 4059 . DOI: 10.1039/c0jm04100a http://doi.org/10.1039/c0jm04100a .

Zhou, H.; Chua, M. H.; Tang, B. Z.; Xu, J. . Aggregation-induced emission (AIE)-active polymers for explosive detection . Polym. Chem. , 2019 . 10 3822 - 3840 . DOI: 10.1039/C9PY00322C http://doi.org/10.1039/C9PY00322C .

Wu, X.; Tong, H.; Wang, L. . Fluorescent polymer materials for detection of explosives . Prog. Chem. , 2019 . 31 1509 - 1527 . .

Huang, W.; Bender, M.; Seehafer, K.; Wacker, I.; Schröder, R. R.; Bunz, U. H. F. . A tetraphenylethene-based polymer array discriminates nitroarenes . Macromolecules , 2018 . 51 1345 - 1350 . DOI: 10.1021/acs.macromol.7b02590 http://doi.org/10.1021/acs.macromol.7b02590 .

Wu. Y.; Qin, A.; Tang, B. Z. . AIE-active polymers for explosive detection . Chinese J. Polym. Sci. , 2017 . 35 141 - 154 . DOI: 10.1007/s10118-017-1882-0 http://doi.org/10.1007/s10118-017-1882-0 .

Han, T.; Zhao, Z.; Lam, J. W. Y.; Tang, B. Z. . Monomer stoichiometry imbalance-promoted formation of multisubstituted polynaphthalenes by palladium-catalyzed polycouplings of aryl iodides and internal diynes . Polym. Chem. , 2018 . 9 885 - 893 . DOI: 10.1039/C7PY01926B http://doi.org/10.1039/C7PY01926B .

浏览量

112

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Facile Synthesis of Functional Poly(methyltriazolylcarboxylate)s by Solvent- and Catalyst-free Butynoate-Azide Polycycloaddition

Aggregation-induced Emission-active Hyperbranched Poly(tetrahydro-pyrimidine)s Synthesized from Multicomponent Tandem Polymerization

Boosting Blood-Brain Barrier Crossing with a Mannosylated Nanocarrier

Composition-dependent Emission in Bifuran-based Polyester Films Doped with Aggregation-induced Emission Luminogen for Information Storage and Encryption

Multicomponent Polymerization of Alkynes, Amines, and Benzaldehyde toward Main-chain Charged Aggregation-induced Emission Polyelectrolytes