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Syntheses and Properties of Ladder-type π-Conjugated Compounds Containing a Benzo[2,1-b:3,4-b′]dithiophene Skeleton

Syntheses and Properties of Ladder-type π-Conjugated Compounds Containing a... Two kinds of ladder-type thiophene-fused π-conjugated compounds, benzo[2,1-b:3,4-b′]bis[1]benzothiophene (syn-BBBT) and dinaphtho[2,3-d:2′,3′-d′]benzo[2,1-b:3,4-b′]dithio-phene (syn-DNBDT), were successfully synthesized. Photophysical and electrochemical properties were evaluated by UV–vis and photoluminescence spectroscopies and cyclic voltammetry as well as theoretical calculations. These properties were compared with those of structural isomers and oxygen analogs to reveal the effect of the fused position of thiophene rings and the fused heteroaromatic rings on π-conjugation. Field-effect transistors with the thin films of syn-BBBT and syn-DNBDT demonstrated typical p-type semiconductor characteristics with relatively high mobilities of <1.3 × 10−1 cm2 V−1 s−1. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Bulletin of the Chemical Society of Japan Oxford University Press

Syntheses and Properties of Ladder-type π-Conjugated Compounds Containing a Benzo[2,1-b:3,4-b′]dithiophene Skeleton

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References (42)

Publisher
Oxford University Press
Copyright
© 2016 The Chemical Society of Japan
ISSN
0009-2673
eISSN
1348-0634
DOI
10.1246/bcsj.20160125
Publisher site
See Article on Publisher Site

Abstract

Two kinds of ladder-type thiophene-fused π-conjugated compounds, benzo[2,1-b:3,4-b′]bis[1]benzothiophene (syn-BBBT) and dinaphtho[2,3-d:2′,3′-d′]benzo[2,1-b:3,4-b′]dithio-phene (syn-DNBDT), were successfully synthesized. Photophysical and electrochemical properties were evaluated by UV–vis and photoluminescence spectroscopies and cyclic voltammetry as well as theoretical calculations. These properties were compared with those of structural isomers and oxygen analogs to reveal the effect of the fused position of thiophene rings and the fused heteroaromatic rings on π-conjugation. Field-effect transistors with the thin films of syn-BBBT and syn-DNBDT demonstrated typical p-type semiconductor characteristics with relatively high mobilities of <1.3 × 10−1 cm2 V−1 s−1.

Journal

Bulletin of the Chemical Society of JapanOxford University Press

Published: May 30, 2016

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