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Issue 30, 2013
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Synthesis and properties of a benzo[1,2-b:4,5-b′]dithiophene core π-system that bears alkyl, alkylthio and alkoxy groups at 3,7-positions

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Abstract

A synthetic sequence was developed to provide 3,7-didodecylbenzo[1,2-b:4,5-b′]dithiophene and its dialkylthio and dialkoxy analogues as planar and soluble building-blocks for constructing benzodithiophene-based π-systems. The benzodithiophenes were also transformed to the corresponding 2,6-di(5-phenyl-2-thienyl)-capped derivatives as the representative oligomers. Their absorption and emission spectra as well as CV data showed that the HOMO–LUMO energy gaps of the dialkylthio and dialkoxy derivatives are smaller than that of the dialkyl one, which is attributable to the lower ELUMO as well as EHOMO energies of the dialkylthio analogue and the higher EHOMO energy of the dialkoxy analogue, respectively. The intra- and intermolecular charge-carrier mobilities were then estimated by the flash-photolysis time-resolved microwave conductivity (FP-TRMC) method and solution-processed top contact FET performance. The TRMC method showed similar high intrinsic hole mobilities (0.16–0.24 cm2 V−1 s−1) irrespective of the substituents, whereas the dialkyl derivative especially displayed a good field-effect mobility of 0.023 cm2 V−1 s−1.

Graphical abstract: Synthesis and properties of a benzo[1,2-b:4,5-b′]dithiophene core π-system that bears alkyl, alkylthio and alkoxy groups at 3,7-positions

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Publication details

The article was received on 31 Jan 2013, accepted on 29 Apr 2013 and first published on 30 Apr 2013


Article type: Paper
DOI: 10.1039/C3RA41822G
RSC Adv., 2013,3, 12356-12365

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    Synthesis and properties of a benzo[1,2-b:4,5-b′]dithiophene core π-system that bears alkyl, alkylthio and alkoxy groups at 3,7-positions

    S. Ota, S. Minami, K. Hirano, T. Satoh, Y. Ie, S. Seki, Y. Aso and M. Miura, RSC Adv., 2013, 3, 12356
    DOI: 10.1039/C3RA41822G

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