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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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Publication details

The article was received on 16 Nov 2012, accepted on 07 Dec 2012 and first published on 10 Dec 2012


Article type: Paper
DOI: 10.1039/C2DT32738D
Citation: Dalton Trans., 2013,42, 3646-3652
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    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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