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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
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 (M w 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.

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Copyright © Materials Research Society 2014 

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References

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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
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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
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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
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