Transition-metal-catalyzed facile access to 3,11-dialkylfulminenes for transistor applications

Masahito Murai; Hiroyuki Maekawa; Shino Hamao; Yoshihiro Kubozono; David Roy; Kazuhiko Takai

doi:10.1021/ol503723j

Transition-metal-catalyzed facile access to 3,11-dialkylfulminenes for transistor applications

Masahito Murai, Hiroyuki Maekawa, Shino Hamao, Yoshihiro Kubozono, David Roy, Kazuhiko Takai

Research Institute for Interdisciplinary Science

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

Novel [6]phenacenes (fulminenes) with two long alkyl chains at the axis positions were synthesized. This short synthesis comprises the following three steps: (1) ruthenium-catalyzed direct C-H bond arylation; (2) conversion of directing groups by Wittig reaction; and (3) bismuth- or gold-catalyzed cyclization of vinyl ether. Organic field-effect transistor devices fabricated with a thin film of 3,11-di(tetradecyl)fulminene exhibited typical p-channel normally-off properties.

Original language	English
Pages (from-to)	708-711
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	3
DOIs	https://doi.org/10.1021/ol503723j
Publication status	Published - Feb 6 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol503723j

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title = "Transition-metal-catalyzed facile access to 3,11-dialkylfulminenes for transistor applications",

abstract = "Novel [6]phenacenes (fulminenes) with two long alkyl chains at the axis positions were synthesized. This short synthesis comprises the following three steps: (1) ruthenium-catalyzed direct C-H bond arylation; (2) conversion of directing groups by Wittig reaction; and (3) bismuth- or gold-catalyzed cyclization of vinyl ether. Organic field-effect transistor devices fabricated with a thin film of 3,11-di(tetradecyl)fulminene exhibited typical p-channel normally-off properties.",

author = "Masahito Murai and Hiroyuki Maekawa and Shino Hamao and Yoshihiro Kubozono and David Roy and Kazuhiko Takai",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

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doi = "10.1021/ol503723j",

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T1 - Transition-metal-catalyzed facile access to 3,11-dialkylfulminenes for transistor applications

AU - Murai, Masahito

AU - Maekawa, Hiroyuki

AU - Hamao, Shino

AU - Kubozono, Yoshihiro

AU - Roy, David

AU - Takai, Kazuhiko

PY - 2015/2/6

Y1 - 2015/2/6

N2 - Novel [6]phenacenes (fulminenes) with two long alkyl chains at the axis positions were synthesized. This short synthesis comprises the following three steps: (1) ruthenium-catalyzed direct C-H bond arylation; (2) conversion of directing groups by Wittig reaction; and (3) bismuth- or gold-catalyzed cyclization of vinyl ether. Organic field-effect transistor devices fabricated with a thin film of 3,11-di(tetradecyl)fulminene exhibited typical p-channel normally-off properties.

AB - Novel [6]phenacenes (fulminenes) with two long alkyl chains at the axis positions were synthesized. This short synthesis comprises the following three steps: (1) ruthenium-catalyzed direct C-H bond arylation; (2) conversion of directing groups by Wittig reaction; and (3) bismuth- or gold-catalyzed cyclization of vinyl ether. Organic field-effect transistor devices fabricated with a thin film of 3,11-di(tetradecyl)fulminene exhibited typical p-channel normally-off properties.

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JO - Organic Letters

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Transition-metal-catalyzed facile access to 3,11-dialkylfulminenes for transistor applications

Abstract

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