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Modular synthesis and photophysical and electrochemical properties of 2,3,5,6-tetraaryl-substituted benzo[1,2-b:5,4-b′]difurans

✍ Scribed by Hayato Tsuji; Chikahiko Mitsui; Yoshiharu Sato; Eiichi Nakamura

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
237 KB
Volume
22
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

We developed a versatile synthesis of tetraaryl‐substituted benzo[1,2‐b:5,4‐b′]difurans (m‐BDFs) via a zinc‐mediated intramolecular double cyclization reaction of 4,6‐bis(phenylethynyl)‐1,3‐benzenediol, followed by a palladium‐catalyzed cross‐coupling reaction. In comparison with the corresponding benzo[1,2‐b:4,5‐b′]difuran (p‐BDF) isomers reported previously, the m‐BDFs are slightly wider between HOMO and LUMO, as well as a lower energy level of the former. These differences in properties between the structural isomers can be ascribed to the difference in the conjugation type. The compounds had high charge carrier mobility up to 1 × 10^−3^ cm^2^/Vs, which makes them attractive materials for organoelectronics applications. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:316–324, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20682

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