Issue 8, 2012

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
10 Feb 2012
Accepted
11 May 2012
First published
14 May 2012

Chem. Sci., 2012,3, 2598-2606

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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