Issue 5, 2013
From the journal:

Polymer Chemistry

Stoichiometric imbalance-promoted synthesis of polymers containing highly substituted naphthalenes: rhodium-catalyzed oxidative polycoupling of arylboronic acids and internal diynes

Meng Gao,a   Jacky W. Y. Lam,a   Jie Li,a   Carrie Y. K. Chan,a   Yilong Chen,a   Na Zhao,a   Tianyu Hana  and  Ben Zhong Tang*ab  

* Corresponding authors

a Department of Chemistry, Institute for Advanced Study, State Key Laboratory of Molecular Neuroscience, Institute of Molecular Functional Materials and Division of Biomedical Engineering, The Hong Kong University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong, China
E-mail: tangbenz@ust.hk

b State Key Laboratory of Luminescent Materials and Devices, Institute of Polymer Optoelectronic Materials and Devices, South China University of Technology, Guangzhou, China

Abstract

A new route for the synthesis of functional polymers was developed. Oxidative polycoupling of 4,4′-(α,ω-alkylenedioxy) bis(diphenylacetylene)s with phenylboronic acid and (1,1,2-triphenylvinyl)phenylboronic acid, respectively, was catalyzed by [Cp*RhCl2]2 and oxidants in dimethylformamide, affording soluble polymers with highly substituted naphthalene rings in satisfactory yields with moderate molecular weights. All the polymers were thermally and morphologically stable, showing high thermal-degradation and glass-transition temperatures of 317–404 °C and 95–168 °C, respectively. They were film-forming and their thin solid films showed high refractive indices (RI = 1.7414–1.6038) in a wide wavelength region of 400–1600 nm. The polymer carrying tetraphenylethene unit was weakly emissive in solution but emitted intensely in the condensed phase, displaying a phenomenon of aggregation-induced emission. The emission of its nanoaggregates could be quenched by picric acid with large quenching constants, making it promising as a sensitive chemosensor for efficient detection of explosives.

Graphical abstract: Stoichiometric imbalance-promoted synthesis of polymers containing highly substituted naphthalenes: rhodium-catalyzed oxidative polycoupling of arylboronic acids and internal diynes

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Article information

DOI
https://doi.org/10.1039/C2PY20758C
Article type
Paper
Submitted
17 Sep 2012
Accepted
17 Oct 2012
First published
18 Oct 2012

Polym. Chem., 2013,4, 1372-1380

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Stoichiometric imbalance-promoted synthesis of polymers containing highly substituted naphthalenes: rhodium-catalyzed oxidative polycoupling of arylboronic acids and internal diynes

M. Gao, J. W. Y. Lam, J. Li, C. Y. K. Chan, Y. Chen, N. Zhao, T. Han and B. Z. Tang, Polym. Chem., 2013, 4, 1372 DOI: 10.1039/C2PY20758C

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