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Issue 8, 2012
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3-Vinylborane-functionalized oligothiophenes: isomer-dependent electronic structure and fluorescence enhancement upon anion binding

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Abstract

The effect of pendant conjugated vinylborane moieties on the electronic structure of oligothiophenes and their anion binding behaviour was investigated. The vinylborane groups were introduced by hydroboration of alkynyl-functionalized 2,5-dibromothiophene with dimesitylborane (Mes2BH). The reaction yielded a 1 : 1 mixture of the α- and β-borylated isomers, which were separated and individually isolated by reverse-phase column chromatography. Grignard metathesis polymerization (GRIM) of the dibromothiophenes yielded oligomeric materials (Mn = 1.5 to 1.7 kDa) capable of anion binding. DFT analyses on borane-functionalized terthiophene model compounds indicated that efficient extension of conjugation from the thiophene main chain to the vinylborane pendant group in the sterically less encumbered β-isomer greatly impacts on the photophysical properties. Anion titration experiments revealed the strong binding of F and CN, which is accompanied by a fluorescence enhancement that is especially pronounced for the β-isomer.

Graphical abstract: 3-Vinylborane-functionalized oligothiophenes: isomer-dependent electronic structure and fluorescence enhancement upon anion binding

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Publication details

The article was received on 10 Feb 2012, accepted on 11 May 2012 and first published on 14 May 2012


Article type: Edge Article
DOI: 10.1039/C2SC20177A
Citation: Chem. Sci., 2012,3, 2598-2606

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    3-Vinylborane-functionalized oligothiophenes: isomer-dependent electronic structure and fluorescence enhancement upon anion binding

    F. Pammer and F. Jäkle, Chem. Sci., 2012, 3, 2598
    DOI: 10.1039/C2SC20177A

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