Regioselective Metal-Free Click Polymerization of Azides and Alkynes
Corresponding Author
Anjun Qin
Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 China
E-mail: [email protected], [email protected]Search for more papers by this authorYong Liu
Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 China
Search for more papers by this authorCorresponding Author
Ben Zhong Tang
Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 China
Department of Chemistry, Institute for Advanced Study, Institute of Molecular Functional Materials and State Key Laboratory of Molecular Neuroscience, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China
E-mail: [email protected], [email protected]Search for more papers by this authorCorresponding Author
Anjun Qin
Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 China
E-mail: [email protected], [email protected]Search for more papers by this authorYong Liu
Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 China
Search for more papers by this authorCorresponding Author
Ben Zhong Tang
Guangdong Innovative Research Team, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 China
Department of Chemistry, Institute for Advanced Study, Institute of Molecular Functional Materials and State Key Laboratory of Molecular Neuroscience, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China
E-mail: [email protected], [email protected]Search for more papers by this authorAbstract
The Cu(I)-catalyzed azide-alkyne click polymerization is well developed and broadly applied to the preparation of functional polymers. The removal of copper residues from the resultant polymers is, however, difficult. One way to completely circumvent this difficulty is to develop click polymerization without the use of metallic catalysts, i.e., metal-free click polymerization (MFCP). Herein, recent efforts towards developing MFCP of activated alkynes and azides, and of activated azides and alkynes, to produce regioregular polytriazoles are summarized, and the properties and applications of the resultant polymers are also briefly discussed.
References
- 1H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004.
10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 CAS PubMed Web of Science® Google Scholar
- 2a) V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596;
10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 CAS PubMed Web of Science® Google Scholarb) C. W. Tornøe, C. Christensen, M. J. Meldal, J. Org. Chem. 2002, 67, 3057.
- 3A. J. Scheel, H. Komber, B. Voit, Macromol. Rapid Commun. 2004, 25, 1175.
- 4a) D. Z. Li, X. Wang, Y. T. Jia, A. Q. Wang, Y. G. Wu, Chin. J. Chem. 2012, 30, 861; b) C. N. Lo, C. S. Hsu, J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 3355; c) J. S. Park, Y. H. Kim, M. Song, C. H. Kim, M. A. Karim, J. W. Lee, Y. S. Gal, P. Kumar, S. W. Kang, S. H. Jin, Macromol. Chem. Phys. 2010, 211, 2464; d) E. Schwartz, K. Breitenkamp, V. V. Fokin, Macromolecules 2011, 44, 4735; e) B. S. Sumerlin, A. P. Vogt, Macromolecules 2010, 43, 1; f) Z. A. Li, W. Wu, G. Qiu, G. Yu, Y. Liu, C. Ye, J. Qin, Z. Li, J. Polym. Sci. Part A: Polym. Chem. 2010, 49, 1977; g) P. L. Golas, K. Matyjaszewski, Chem. Soc. Rev. 2010, 39, 1338; h) X. Q. Xue, J. Zhu, Z. B. Zhang, N. C. Zhou, Y. F. Tu, X. L. Zhu, Macromolecules 2010, 43, 2704; i) W. H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 2008, 29, 952; j) F. Y. Deng, B. Xu, Y. Gao, Z. Liu, D. G. Yang, H. M. Li, J. Polym. Sci. Part A: Polym. Chem. 2012, 50, 3767.
- 5a) C. Barner-Kowollik, F. E. Du Prez, P. Espeel, C. J. Hawker, T. Junkers, H. Schlaad, W. V. Camp, Angew. Chem. Int. Ed. 2011, 50, 60; b) R. K. Iha, K. L. Wooley, A. M. Nystrom, D. J. Burke, M. J. Kade, C. J. Hawker, Chem. Rev. 2009, 109, 5620; c) K. Kempe, A. Krieg, C. R. Becer, U. S. Schubert, Chem. Soc. Rev. 2012, 41, 176; d) S. Pandey, S. P. Mishra, B. Kolli, T. Kanai, A. B. Samui, J. Polym. Sci. Part A: Polym. Chem. 2012, 50, 2659; e) W. Wu, C. Ye, G. Yu, Y. Liu, J. Qin, Z. Li, Chem. Eur. J. 2012, 18, 4426; f) O. Plietzsch, C. I. Schilling, T. Grab, S. L. Grage, A. S. Ulrich, A. Comotti, P. Sozzani, T. Muller, S. Brase, New J. Chem. 2011, 35, 1577; g) A. R. Katritzky, Y. M. Song, R. Sakhuja, R. Gyanda, N. K. Meher, L. Wang, R. S. Duran, D. A. Ciaramitaro, C. D. Bedford, J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 3748; j) L. Yang, X. Liu, X. Tan, H. Yang, Z. Wang, X. Zhang, Polym. Chem. 2014, 5, 323.
- 6a) H. Li, J. Z. Sun, A. Qin, B. Z. Tang, Chin. J. Polym. Sci. 2012, 30, 1; b) A. J. Qin, J. W. Y. Lam, B. Z. Tang, Chem. Soc. Rev. 2010, 39, 2522; c) A. J. Qin, J. W. Y. Lam, B. Z. Tang, Macromolecules 2010, 43, 8693.
- 7a) J. Liu, J. W. Y. Lam, B. Z. Tang, Chem. Rev. 2009, 109, 5799; b) R. Hu, J. W. Y. Lam, B. Z. Tang, Macromol. Chem. Phys. 2013, 214, 175.
- 8A. J. Qin, M. Häuβler, J. W. Y. Lam, K. K. C. Tse, B. Z. Tang, Polym. Prepr. 2006, 47, 681.
- 9a) A. Qin, J. W. Y. Lam, C. K. W. Jim, L. Zhang, J. Yan, M. Häussler, J. Liu, Y. Dong, D. Liang, E. Chen, G. Jia, B. Z. Tang, Macromolecules 2008, 41, 3808; b) A. J. Qin, J. W. Y. Lam, L. Tang, C. K. W. Jim, H. Zhao, J. Z. Sun, B. Z. Tang, Macromolecules 2009, 42, 1421; c) J. Wang, J. Mei, W. Z. Yuan, P. Lu, A. J. Qin, J. Z. Sun, Y. G. Ma, B. Z. Tang, J. Mater. Chem. 2011, 21, 4056; d) J. Wang, J. Mei, E. G. Zhao, Z. G. Song, A. J. Qin, J. Z. Sun, B. Z. Tang, Macromolecules 2012, 45, 7692; e) E. G. Zhao, H. K. Li, J. Ling, H. Q. Wu, J. Wang, S. Zhang, J. W. Y. Lam, J. Z. Sun, A. J. Qin, B. Z. Tang, Polym. Chem. 2014, 5, 2301.
- 10a) L. M. Gaetke, C. K. Chow, Toxicology 2003, 189, 147; b) Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn, J. Am. Chem. Soc. 2003, 125, 3192; c) J. Zhang, K. Zhang, X. Huang, W. Cai, C. Zhou, S. Liu, F. Huang, Y. Cao, J. Mater. Chem. 2012, 22, 12759.
- 11H. Q. Wu, H. K. Li, R. T. K. Kwok, E. G. Zhao, J. Z. Sun, A. J. Qin, B. Z. Tang, Sci. Rep. 2014, 4, 5107.
- 12a) C. Barner-Kowollik, F. E. Du Prez, P. Espeel, C. J. Hawker, T. Junkers, H. Schlaad, W. Van Camp, Angew. Chem. Int. Ed. 2011, 50, 60; b) W. Li, T. Tian, W. Zhu, J. C. Cui, Y. Ju, G. T. Li, Polym. Chem. 2013, 4, 3057.
- 13R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry (Ed. A. Padwa), Wiley, New York 1984, pp 1.
- 14a) F. Gonzaga, L. P. Sadowski, T. Rambarran, J. Grande, A. Adronov, M. A. Brook, J. Polym. Sci. Part A: Polym. Chem. 2013, 51, 1272; b) B. Sandmann, B. Happ, J. Vitz, R. M. Paulus, M. D. Hager, P. Burtscher, N. Moszner, U. S. Schubert, Macromol. Chem. Phys. 2014, 215, 1603; c) Q. Wei, H. Q. Deng, Y. B. Cai, J. W. Y. Lam, J. Li, J. Z. Sun, M. Gao, A. J. Qin, B. Z. Tang, Macromol. Rapid Commun. 2012, 33, 1356; d) F. Gonzaga, G. Yu, M. A. Brook, Macromolecules 2009, 42, 9220.
- 15a) J. M. Baskin, J. A. Prescher, S. T. Laughlin, N. J. Agard, P. V. Chang, I. A. Miller, A. Lo, J. A. Codelli, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2007, 104, 16793; b) S. T. Laughlin, J. M. Baskin, S. L. Amacher, C. R. Bertozzi, Science 2008, 320, 664.
- 16C. R. Becer, R. Hoogenboom, U. S. Schubert, Angew. Chem. Int. Ed. 2009, 48, 4900.
- 17a) H. C. Dong, R. Zheng, J. W. Y. Lam, M. Häußler, B. Z. Tang, Macromolecules 2005, 38, 6382; b) A. J. Qin, J. W. Y. Lam, H. C. Dong, W. X. Lu, C. K. W. Jim, Y. Q. Dong, M. Häuβler, H. H. Y. Sung, I. D. Williams, G. K. L. Wong, B. Z. Tang, Macromolecules 2007, 40, 4879.
- 18A. J. Qin, C. K. W. Jim, W. X. Lu, J. W. Y. Lam, M. Häuβler, Y. Q. Dong, H. H. Y. Sung, I. D. Williams, G. K. L. Wong, B. Z. Tang, Macromolecules 2007, 40, 2308.
- 19a) J. Luo, Z. Xie, J. W. Y. Lam, L. Cheng, H. Chen, C. Qiu, H. S. Kwok, X. Zhao, Y. Liu, D. Zhu, B. Z. Tang, Chem. Commun. 2001, 1740; b) A. Qin, J. W. Y. Lam, B. Z. Tang, Prog. Polym. Sci. 2012, 37, 182; c) Y. Hong, J. W. Y. Lam, B. Z. Tang, Chem. Soc. Rev. 2011, 40, 5361; d) M. Wang, G. Zhang, D. Zhang, D. Zhu, B. Z. Tang, J. Mater. Chem. 2010, 20, 1858; e) Y. Hong, J. W. Y. Lam, B. Z. Tang, Chem. Commun. 2009, 4332; f) Z. Zhao, J. W. Y. Lam, B. Z. Tang, J. Mater. Chem. 2012, 22, 23726; g) J. Huang, N. Sun, Y. Dong, R. Tang, P. Lu, P. Cai, Q. Li, D. Ma, J. Qin, Z. Li, Adv. Funct. Mater. 2013, 23, 2329; h) X. G. Gu, J. J. Yao, G. X. Zhang, C. Zhang, Y. L. Yan, Y. S. Zhao, D. Q. Zhang, Chem. Asian J. 2013, 8, 2362; i) X. Zhang, Z. Chi, X. Zhou, S. Liu, Y. Zhang and J. Xu, J. Phys. Chem. C. 2012, 116, 23629; j) J. Ma, T. T. Lin, X. Y. Pan, W. Z. Wang, Chem. Mater. 2014, 26, 4221; k) R. Misra, T. Jadhav, B. Dhokale, S. M. Mobin, Chem. Commun. 2014, 50, 9067; l) K. R. Ghosh, S. K. Saha, Z. Y. Wang, Polym. Chem. 2014, 5, 5638; m) K. Li, B. Liu, Chem. Soc. Rev. 2014, 43, 6570.
- 20A. J. Qin, L. Tang, J. W. Y. Lam, C. K. W. Jim, Y. Yu, H. Zhao, J. Z. Sun, B. Z. Tang, Adv. Funct. Mater. 2009, 19, 1891.
- 21Q. Wei, J. Wang, X. Shen, X. Zhang, J. Z. Sun, A. Qin, B. Z. Tang, Sci. Rep. 2013, 3, 1093.
- 22A. J. Qin, C. K. W. Jim, J. W. Y. Lam, J. Z. Sun, B. Z. Tang, Chin. J. Polym. Sci. 2009, 27, 145.
- 23a) A. R. Katritzky, N. K. Meher, S. Hanci, R. Gyanda, S. R. Tala, S. Mathai, R. S. Duran, S. Bernard, F. Sabri, S. K. Singh, J. Doskocz, D. A. Ciaramitaro, J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 238; b) A. R. Katritzky, Y. M. Song, R. Sakhuja, R. Gyanda, N. K. Meher, L. Wang, R. S. Duran, D. A. Ciaramitaro, C. D. Bedford, J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 3748.
- 24a) H. K. Li, J. Mei, J. Wang, S. Zhang, Q. Zhao, Q. Wei, A. J. Qin, J. Z. Sun, B. Z. Tang, Sci. China Chem. 2011, 54, 611; b) H. K. Li, J. Wang, J. Z. Sun, R. Hu, A. J. Qin, B. Z. Tang, Polym. Chem. 2012, 3, 1075; c) H. K. Li, H. Q. Wu, E. G. Zhao, J. Li, J. Z. Sun, A. J. Qin, B. Z. Tang, Macromolecules 2013, 46, 3907; d) H. K. Li, L. Z. Li, H. Q. Wu, J. W. Y. Lam, J. Z. Sun, A. J. Qin, B. Z. Tang, Polym. Chem. 2013, 4, 5537; e) H. K. Li, Z. Wang, J. Li, E. G. Zhao, J. Z. Sun, J. W. Y. Lam, A. J. Qin, B. Z. Tang, Macromol. Chem. Phys. 2014, 215, 1036.
- 25J. W. Li, Y. Li, C. Y. K. Chan, R. T. K. Kwok, H. K. Li, P. Zrazhevskiy, X. H. Gao, J. Z. Sun, A. J. Qin, B. Z. Tang, Angew. Chem. Int. Ed. 2015, 53, 13518.
- 26a) Q. Wang, H. K. Li, Q. Wei, J. Z. Sun, J. Wang, X. A. Zhang, A. J. Qin, B. Z. Tang, Polym. Chem. 2013, 4, 1396; b) Q. Wang, M. Chen, B. Yao, J. Wang, J. Mei, J. Z. Sun, A. J. Qin, B. Z. Tang, Macromol. Rapid Commun. 2013, 34, 796.
- 27a) W. Wu, Z. Zhu, G. Qiu, C. Ye, J. Qin, Z. Li, J. Polym. Sci. Part A: Polym. Chem. 2012, 50, 5124; b) B.-B. Ni, C. Wang, H. Wu, J. Pei, Y. Ma, Chem. Commun. 2010, 46, 782; c) E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. Int. Ed. 2003, 42, 1210; d) C. R. Patrick, G. S. Prosser, Nature 1960, 187, 1020.
