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Issue 10, 2013
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Synthesis of dithienosilole-based highly photoluminescent donor–acceptor type compounds

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Abstract

Highly photoluminescent acceptor–donor–acceptor (A–D–A) and donor–acceptor (D–A) type compounds with a dithienosilole unit as the donor and perfluorotolyl or dimesitylboryl group(s) as the acceptor were prepared by the reaction of lithiated dithienosilole derivatives with perfluorotoluene or fluorodimesitylborane, respectively. The resulting A–D–A and D–A type compounds showed red-shifted UV absorption and PL bands compared to those of simple dithienosiloles having no acceptor units, reported previously, and were highly photoluminescent in the solid state as well as in solution. Solvatochromic behaviour that would arise from the intramolecular donor–acceptor interaction were observed for the D–A type compounds with respect to the UV absorption and PL spectra. In addition, it was found that bis(dimesitylboryl)dithienosilole and (dimesitylboryl)(methylthio)dithienosilole responded to coexisting fluoride anions, leading to clear UV absorption and PL spectral changes in solutions.

Graphical abstract: Synthesis of dithienosilole-based highly photoluminescent donor–acceptor type compounds

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Article information


Submitted
16 Nov 2012
Accepted
07 Dec 2012
First published
10 Dec 2012

Dalton Trans., 2013,42, 3646-3652
Article type
Paper

Synthesis of dithienosilole-based highly photoluminescent donor–acceptor type compounds

J. Ohshita, Y. Tominaga, D. Tanaka, Y. Ooyama, T. Mizumo, N. Kobayashi and H. Higashimura, Dalton Trans., 2013, 42, 3646 DOI: 10.1039/C2DT32738D

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