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Rhodium-Catalyzed Oxidative Polycoupling of Phenylpyrazole and Internal Diynes: A New Polymerization Route for Atom-Economical Synthesis of Poly(pyrazolylnaphthalene)s

Published online by Cambridge University Press:  10 February 2014

Yajing Liu ,
Meng Gao ,
Jie Li  and
Ben Zhong Tang
Yajing Liu
Affiliation:
Department of Chemistry, Institute for Advanced Study and Division of Biomedical Engineering, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China. Email: tangbenz@ust.hk
Meng Gao
Affiliation:
Department of Chemistry, Institute for Advanced Study and Division of Biomedical Engineering, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China. Email: tangbenz@ust.hk
Jie Li
Affiliation:
Department of Chemistry, Institute for Advanced Study and Division of Biomedical Engineering, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China. Email: tangbenz@ust.hk
Ben Zhong Tang
Affiliation:
Department of Chemistry, Institute for Advanced Study and Division of Biomedical Engineering, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China. Email: tangbenz@ust.hk
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Abstract

A new route for atom-economical synthesis of functional polymers was developed. Oxidative polycoupling of 3,5-dimethyl-1-phenylpyrazole with 4,4’-(α,ω-alkylenedioxy) bis(diphenylacetylene)s and 1,2-diphenyl-1,2-bis[4-(phenylethynyl)phenyl]ethene, respectively, were catalyzed by [Cp*RhCl2]2, 1,2,3,4-tetraphenylcyclopenta-1,3-diene and copper(II) acetate in dimethylformamide under stoichiometric imbalance conditions, affording soluble poly(pyrazolylnaphthalene)s in satisfactory yields (isolation yield up to 82%) with high molecular weights (Mw up to 35700). All the polymers were thermally stable, losing little of their weight at high temperatures of 323–422 oC. They possessed good film-forming property and their thin solid films showed high refractive indices (RI = 1.747–1.593) in a wide wavelength region of 400−1000 nm. The polymer carrying tetraphenylethene unit displayed a phenomenon of aggregation-induced emission and showed enhanced light emission in the aggregated state.

Keywords

polymerizationsensorfilm
Type
Articles
Information
MRS Online Proceedings Library (OPL) , Volume 1613: Symposium 4D – New Trends in Polymer Chemistry and Characterization-2013 , 2014 , pp. 3 - 15
Copyright
Copyright © Materials Research Society 2014 

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References

REFERENCES

Shirakawa, H., Angew. Chem. Int. Ed., 40, 2575–2580(2001); (b) A. G. MacDiarmid, Angew. Chem. Int. Ed., 40, 2581–2590(2001); (c) A. J. Heeger, Angew. Chem. Int. Ed., 40, 2591–2611 (2001). 1. (a) J. L. Liu, J. W. Y. and B. Z. Tang, Chem. Rev., 109, 5799–5867 (2009); (b) A. Qin, J. W. Y. Lam and B. Z. Tang, Chem. Soc. Rev. 39, 2522–2544 (2010); (c) J. W. Y. Lam and B. Z. Tang, Acc. Chem. Res., 38, 745–754 (2005); (d) A. Qin, J. W. Y. Lam and B. Z. Tang, Prog. Polym. Sci., 37, 182–209 (2012); (e) S. K. Choi, Y. S. Gal, S. H. Jin and H. K. Kim, Chem. Rev., 100, 1645−1681 (2000); (f) H. F. Bunz, Acc. Chem. Res., 34, 998−1010 (2001); (g) M. B. Nielsen and F. Diederich, Chem. Rev., 105, 1837−1867 (2005); (h) W. Zhang and J. S. Moore, Angew. Chem. Int., 45, 4416-4439 (2006); (i) T. J. Masuda, Polym. Sci. Part A: Polym. Chem., 45, 165−180 (2007); (j) J. Wu, W. Pisula and K. Mullen, Chem. Rev., 107, 718−747 (2007); (k) S. W. Thomas, G. D. Joly and T. Swager, Chem. Rev., 107, 1339−1386 (2007); (l) Y. Morisakia and Y. Chujo, Prog. Polym. Sci., 33, 346−364 (2008).3.0.CO;2-N>CrossRefGoogle Scholar
J. B. Shi, C. J. W. Jim, F. Mahtab, J. Z. Liu, J. W. Y. Lam, H. H. Y. Sung, I. D. Williams, Y. P. Dong and B. Z. Tang, Macromolecules, 43, 680–690 (2010); (b) J. Z. Liu, L. Zhang, J. W. Y. Lam, C. K. W. Jim, Y. A. Yue, R. Deng, Y. N. Hong, A. J. Qin, H. H. Y. Sung, I. D. Williams, G. C. Jia and B. Z. Tang, Macromolecules, 42, 7367–7378(2009); (c) H. Li, J. Wang, J. Z. Sun, R. Hu, A. Qin and B. Z. Tang, Polymer Chemistry, 3, 1075–1083. For selected examples of Diels–Alder reactions, see: (a) H. Mukamal, F. W. Harris and J. K. Stille, J. Polym. Sci. Part A: Polym. Chem., 5, 2721–2729 (1967); (b) A. L. Rusanov, D. Y. Likhachev, P. V. Kostoglodov and N. M. Belomoina, Polym. Sci. Ser. C, 50, 39–62 (2008).Google Scholar
Saleh, M., Baumgarten, M., Mavrinskiy, A., Schäfer, T. and Müllen, K., Macromolecules, 43, 137–143 (2010).CrossRefGoogle Scholar
Li, C., Liu, M., Pschirer, N. G., Baumgarten, M. and Mullen, K., Chem. Rev., 110, 6817–6855 (2010).CrossRefGoogle Scholar
Toal, S. J. and Trogler, W. C., J. Mater. Chem., 16, 2871–2883 (2006).CrossRefGoogle Scholar
Fraind, A. M. and Tovar, J. D., J. Phys. Chem. B, 114, 3104–3116 (2010); (b) J. Feng, X. Chen, Q. Han, H. Wang, P. Lu and Y. Wang, J. Lumin., 131, 2775–2783(2011); (c) V. C. Sundar, J. Zaumseil, V. Podzoror, E. Menard, R. L. Willett, T. Someya, M. E. Gershenson and J. A. Rogers, Science, 303, 1644−1646 (2004); (d) M. S. Goncalves, Chem. Rev., 109, 190−212 (2009); (e) S. Li, J. Xiang, X. Mei and C. Xu, Tetrahedron Lett., 49, 1690−1693 (2008).CrossRefGoogle Scholar
Wakabayashi, K., Kohama, S. I., Yamazaki, S. and Kimura, K., Macromolecules, 41, 1168–1174 (2008); (b) D. Zhao and K. Yue, Macromolecules, 41, 4029–4036(2008); (c) N. Nomura, K. Tsurugi and M. Okada, Angew. Chem. Int. Ed., 40, 1932–1935 (2001); (d) N. Nomura, K. Tsurugi, T. V. RajanBabu and T. Kondo, J. Am. Chem. Soc., 126, 5354–5355 (2004); (e) T. Takemura, K. Sugie, H. Nishino, S. Kawabata and T. Koizumi, J. Polym. Sci. Part A: Polym. Chem., 46, 2250–2261 (2008); (f) N. Kihara, S. Komatsu, T. Takata and T. Endo, Macromolecules, 32, 4776–4783 (1999); (g) H. Iimori, Y. Shibasaki, S. Ando and M. Ueda, Macromol. Symp., 199, 23–35 (2003); (h) T. Dutta, K. B. Woody and M. D. Watson, J. Am. Chem. Soc., 130, 452–453 (2008); (i) A. R. Cruz, M. C. G. Hernandez, M. T. Guzmán–Gutiérrez, M. G. Zolotukhin, S. Fomine, S. L. Morales, H. Kricheldorf, E. S. Wilks, J. Cárdenas and M. Salmón, Macromolecules, 45, 6774–6780 (2012); (j) H. R. Kricheldorf, M. G. Zolotukhin and J. Cardenas, Macromol. Rapid Commun., 33, 1814–1832 (2012).CrossRefGoogle Scholar
Gao, M., Lam, J. W. Y., Li, J., Chan, C. Y. K., Chen, Y., Zhao, N., Han, T. and Tang, B. Z., Polymer Chemistry, DOI: 10.1039/C2PY20758C (2013).Google Scholar
Umeda, N., Hirano, K., Satoh, T., Shibata, N., Sato, H. and Miura, M., J. Org. Chem., 76, 13–24 (2011); (b) N. Umeda, H. Tsurugi, T. Satoh and M. Miura, Angew. Chem., Int. Ed., 47, 4019–4022(2008).Google Scholar
Wang, Z.–X. and Qin, H.–L., Green Chem., 6, 90–92 (2004).CrossRefGoogle Scholar
Hong, Y., Lam, J. W. and Tang, B. Z., Chem. Soc. Rev., 40, 5361–5388 (2011); (b) Y. Hong, J. W. Y. Lam and B. Z. Tang, Chem. Commun., 4332–4353(2009); (c) R. Hu, J. W. Y. Lam, J. Liu, H. H. Y. Sung, I. D. Williams, Z. Yue, K. S. Wong, M. M. F. Yuen and B. Z. Tang, Polym. Chem., 3, 1481–1489 (2012); (d) H. Li, J. Wang, J. Z. Sun, R. Hu, A. Qin and B. Z. Tang, Polym. Chem., 3, 1075–1083 (2012); (e) Z. Zhao, S. Chen, J. W. Y. Lam, C. K. W. Jim, C. Y. K. Chan, Z. Wang, P. Li, C. Peng, H. S. Kwok, Y. Ma and B. Z. Tang, J. Phys. Chem. C, 114, 7963−7972 (2010).Google Scholar
Liu, Y., Deng, C. M., Tang, L., Qin, A. J., Hu, R. R., Sun, J. Z. and Tang, B. Z., J. Am. Chem. Soc., 133, 660–663 (2011).CrossRefGoogle Scholar
Liu, J.–g. and Ueda, M., J. Mater. Chem., 19, 8907–8919 (2009).CrossRefGoogle Scholar
Thomas, S. W., Joly, G. D. and Swager, T. M., Chem. Rev., 107, 1339–1386 (2007); (b) D. Zhao and T. M. Swager, Macromolecules, 38, 9377–9384(2005).CrossRefGoogle Scholar
Liu, J. a, Zhong, Y., Lu, P., Hong, Y., Lam, J. W. Y., Faisal, M., Yu, Y., Wong, K. S. and Tang, B. Z., Polym. Chem., 1, 426–429 (2010).CrossRefGoogle Scholar
Sohn, H., Sailor, M. J., Magde, D. and Trogler, W. C., J. Am. Chem. Soc., 125, 3821–3830 (2003).CrossRefGoogle Scholar
Kang, J. W., Moseley, K. and Maitlis, P. M., J. Am. Chem. Soc., 91, 5970–5977 (1969).CrossRefGoogle Scholar
Vyas, V. S. and Rathore, R., Chem. Commun., 46, 1065–1067 (2010).CrossRefGoogle Scholar