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

Wei-Wen Chi; Rong-Yuan Zhang; Ting Han; Jian Du; Hong-Kun Li; Wei-Jie Zhang; Yong-Fang Li; Ben Zhong Tang

doi:10.1007/s10118-019-2316-y

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

ARTICLE | Updated：2019-09-03

- Facile Synthesis of Functional Poly(methyltriazolylcarboxylate)s by Solvent- and Catalyst-free Butynoate-Azide Polycycloaddition
- Chinese Journal of Polymer Science Vol. 38, Issue 1, Pages: 17-23(2020)
- 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.Department of Urology, The First Affiliated Hospital of Soochow University, Suzhou 215006, 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 (H.K.L.)
  wj539@163.com (W.J.Z.)
  tangbenz@ust.hk (B.Z.T.)
- Funds：
- DOI：10.1007/s10118-019-2316-y
  CLC：
- Received：17 April 2019，
  
  Revised：2019-6-6，
  
  Accepted：13 June 2019，
  
  Online First：03 September 2019，
  
  Published：2020-01
- Accepted：
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Citation: 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

Wei-Wen Chi, Rong-Yuan Zhang, Ting Han, et al. Facile Synthesis of Functional Poly(methyltriazolylcarboxylate)s by Solvent- and Catalyst-free Butynoate-Azide Polycycloaddition[J]. Chinese Journal of Polymer Science, 2020, 38(1): 17-23.
Citation: 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.

Wei-Wen Chi, Rong-Yuan Zhang, Ting Han, et al. Facile Synthesis of Functional Poly(methyltriazolylcarboxylate)s by Solvent- and Catalyst-free Butynoate-Azide Polycycloaddition[J]. Chinese Journal of Polymer Science, 2020, 38(1): 17-23. DOI： 10.1007/s10118-019-2316-y.

摘要

Abstract

The copper-catalyzed and metal-free azide-alkyne click polymerizations have become efficient tools for polymer synthesis. However

the 1

3-dipolar polycycloadditions between internal alkynes and azides are rarely employed to construct functional polymers. Herein

the polycycloadditions of dibutynoate (

) and tetraphenylethene-containing diazides (

) were carried out at 100 °C for 12 h under solvent- and catalyst-free conditions

producing soluble poly(methyltriazolylcarboxylate)s (PMTCs) with high molecular weights in high yields. The resultant polymers were thermally stable with 5% weight loss temperatures up to 377 °C. The PMTCs showed aggregation-induced emission (AIE) properties. They could work as fluorescent sensors for detecting explosive with high sensitivity

and generate two-dimensional fluorescent photopatterns with high resolution. Furthermore

their triazolium salts could be utilized for cell-imaging applications.

关键词

Keywords

references

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 .

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 .

Huisgen R. in 1,3-Dipolar cycloaddition chemistry . (Ed.: A. Padwa) Wiley, New York, 1984 .

Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B . A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective " ligation” of azides and terminal alkynes . Angew. Chem. Int. Ed. , 2002 . 41 2596 - 2599 . DOI: 10.1002/(ISSN)1521-3773 http://doi.org/10.1002/(ISSN)1521-3773 .

Tornøe, C. W.; Christensen, C.; Meldal, M . Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides . J. Org. Chem. , 2002 . 67 3057 - 3064 . DOI: 10.1021/jo011148j http://doi.org/10.1021/jo011148j .

Tiwari, V. K.; Mishra, B. B.; Mishra, K. B.; Mishra, N.; Singh, A. S.; Chen, X . Cu-catalyzed click reaction in carbohydrate chemistry . Chem. Rev. , 2016 . 116 3086 - 3240 . DOI: 10.1021/acs.chemrev.5b00408 http://doi.org/10.1021/acs.chemrev.5b00408 .

Golas, P. L.; Matyjaszewski, K . Marrying click chemistry with polymerization: expanding the scope of polymeric materials . Chem. Soc. Rev. , 2010 . 39 1338 - 1354 . DOI: 10.1039/B901978M http://doi.org/10.1039/B901978M .

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 .

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 .

Li, H.; Qin, A.; Sun, J. Z.; Tang, B. Z . Azide-alkyne click polymerization: an update . Chinese J. Polym. Sci. , 2012 . 30 1 - 15 . DOI: 10.1007/s10118-012-1098-2 http://doi.org/10.1007/s10118-012-1098-2 .

Qin, A.; Lam, J. W. Y.; Tang, B. Z . Click polymerization: progresses, challenges, and opportunities . Macromolecules , 2010 . 43 8693 - 8702 . DOI: 10.1021/ma101064u http://doi.org/10.1021/ma101064u .

Becer, C. R.; Hoogenboom, R.; Schubert, U. S . Click chemistry beyond metal-catalyzed cycloaddition . Angew. Chem. Int. Ed. , 2009 . 48 4900 - 4908 . DOI: 10.1002/anie.v48:27 http://doi.org/10.1002/anie.v48:27 .

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 . DOI: 10.1021/mz500590d http://doi.org/10.1021/mz500590d .

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.v39.11 http://doi.org/10.1002/marc.v39.11 .

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.v216.8 http://doi.org/10.1002/macp.v216.8 .

Ni, B.; Wang, C.; Wu, H.; Pei, J.; Ma, Y . Copper-free cycloaddition of azide and alkyne in crystalline state facilitated by arene-perfluoroarene interactions . Chem. Commun. , 2010 . 46 782 - 784 . DOI: 10.1039/B912337G http://doi.org/10.1039/B912337G .

Meng, X.; Chen, H.; Xu, S.; Ma, Y . Metal-free 1,3-dipolar cycloaddition polymerization via prearrangement of azide and alkyne in the solid state . CrystEngComm , 2014 . 16 9983 - 9986 . DOI: 10.1039/C4CE01690D http://doi.org/10.1039/C4CE01690D .

Pathigoolla, A.; Gonnade, R. G.; Sureshan, K. M . Topochemical click reaction: spontaneous self-stitching of a monosaccharide to linear oligomers through lattice-controlled azide-alkyne cycloaddition . Angew. Chem. Int. Ed. , 2012 . 51 4362 - 4366 . DOI: 10.1002/anie.201201023 http://doi.org/10.1002/anie.201201023 .

Krishnan, B. P.; Sureshan, K. M . Topochemical azide-alkyne cycloaddition reaction in gels: size-tunable synthesis of triazole-linked polypeptides . J. Am. Chem. Soc. , 2017 . 139 1584 - 1589 . DOI: 10.1021/jacs.6b11549 http://doi.org/10.1021/jacs.6b11549 .

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.v215.17 http://doi.org/10.1002/macp.v215.17 .

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.v53.16 http://doi.org/10.1002/pola.v53.16 .

Wei, Q.; Deng, H. Q.; Cai, Y. B.; Lam, J. W. Y.; Li, J.; Sun, J. Z.; Gao, M.; Qin, A.; Tang, B. Z . Efficient polymerization of azide and active internal alkynes . Macromol. Rapid Commun. , 2012 . 33 1356 - 1361 . DOI: 10.1002/marc.201200212 http://doi.org/10.1002/marc.201200212 .

Yuan, W.; Chi, W.; Liu, R.; Li, H.; Li, Y.; Tang, B. Z . Synthesis of poly(phenyltriazolylcarboxylate)s with aggregation-induced emission characteristics by metal-free 1,3-dipolar polycycloaddition of phenylpropiolate and azides . Macromol. Rapid Commun. , 2017 . 38 1600745 DOI: 10.1002/marc.v38.5 http://doi.org/10.1002/marc.v38.5 .

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.v39.24 http://doi.org/10.1002/marc.v39.24 .

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 . .

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 .

Mei, J.; Huang, Y.; Tian, H . Progress and trends in AIE-based bioprobes: a brief overview . ACS Appl. Mater. Interfaces , 2018 . 10 12217 - 12261 . DOI: 10.1021/acsami.7b14343 http://doi.org/10.1021/acsami.7b14343 .

Ding, S.; Liu, M.; Hong, Y . Biothiol-specific fluorescent probes with aggregation-induced emission characteristics . Sci. China Chem. , 2018 . 61 882 - 891 . DOI: 10.1007/s11426-018-9300-5 http://doi.org/10.1007/s11426-018-9300-5 .

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 .

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 .

Liu, M.; Gao, P.; Wan, Q.; Deng, F.; Wei, Y.; Zhang, X . Recent advances and future prospects of aggregation-induced emission carbohydrate polymers . Macromol. Rapid Commun. , 2017 . 38 1600575 DOI: 10.1002/marc.v38.10 http://doi.org/10.1002/marc.v38.10 .

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 .

Campbell, M.; Sharp, D. N.; Harrison, M. T.; Denning, R. G.; Turberfield, A. J . Fabrication of photonic crystals for the visible spectrum by holographic lithography . Nature , 2000 . 404 53 - 56 . DOI: 10.1038/35003523 http://doi.org/10.1038/35003523 .

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 .

Dimitrov-Raytchev, P.; Beghdadi, S.; Serghei, A.; Drockenmuller, E . Main-chain 1,2,3-triazolium-based poly(ionic liquid)s issued from AB + AB click chemistry polyaddition . J. Polym. Sci., Part A: Polym. Chem. , 2013 . 51 34 - 38 . DOI: 10.1002/pola.26326 http://doi.org/10.1002/pola.26326 .

Obadia, M. M.; Jourdain, A.; Serghei, A.; Ikeda, T.; Drockenmuller, E . Cationic and dicationic 1,2,3-triazolium-based poly(ethylene glycol ionic liquid)s . Polym. Chem. , 2017 . 8 910 - 917 . DOI: 10.1039/C6PY02030E http://doi.org/10.1039/C6PY02030E .

Jourdain, A.; Antoniuk, I.; Serghei, A.; Espuche, E.; Drockenmuller, E . 1,2,3-Triazolium-based linear ionic polyurethanes . Polym. Chem. , 2017 . 8 5148 - 5156 . DOI: 10.1039/C7PY00406K http://doi.org/10.1039/C7PY00406K .

Tan, W.; Li, Q.; Dong, F.; Qiu, S.; Zhang, J.; Guo, Z . Novel 1,2,3-triazolium-functionalized starch derivatives: synthesis, characterization, and evaluation of antifungal property . Carbohydr. Polym. , 2016 . 160 163 - 171 . .

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