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Issue 5, 2013
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Stoichiometric imbalance-promoted synthesis of polymers containing highly substituted naphthalenes: rhodium-catalyzed oxidative polycoupling of arylboronic acids and internal diynes

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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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Publication details

The article was received on 17 Sep 2012, accepted on 17 Oct 2012 and first published on 18 Oct 2012


Article type: Paper
DOI: 10.1039/C2PY20758C
Citation: 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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