Naphthodithiophenediimide (NDTI): Synthesis, structure, and applications

Yuta Fukutomi; Masahiro Nakano; Jian Yong Hu; Itaru Osaka; Kazuo Takimiya

doi:10.1021/ja404753r

Naphthodithiophenediimide (NDTI): Synthesis, structure, and applications

Yuta Fukutomi, Masahiro Nakano, Jian Yong Hu, Itaru Osaka, Kazuo Takimiya

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

146 Citations (Scopus)

Abstract

A straightforward synthesis of α,β-unsubstituted and α-halogenated naphtho[2,3-b:6,7-b′]dithiophenediimides (NDTIs) is described. Electrochemical and optical studies of N,N-dioctyl-NDTI demonstrate that the compound has a low-lying LUMO energy level (4.0 eV below the vacuum level) and a small HOMO-LUMO gap (∼2.1 eV). With its interesting electronic and optical properties, in addition to its planar structure, NDTI is a promising building block for the development of novel π-functional materials. In fact, it afforded n-channel, p-channel, and ambipolar materials, depending on the molecular modification.

Original language	English
Pages (from-to)	11445-11448
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	31
DOIs	https://doi.org/10.1021/ja404753r
Publication status	Published - 2013 Aug 7
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "A straightforward synthesis of α,β-unsubstituted and α-halogenated naphtho[2,3-b:6,7-b′]dithiophenediimides (NDTIs) is described. Electrochemical and optical studies of N,N-dioctyl-NDTI demonstrate that the compound has a low-lying LUMO energy level (4.0 eV below the vacuum level) and a small HOMO-LUMO gap (∼2.1 eV). With its interesting electronic and optical properties, in addition to its planar structure, NDTI is a promising building block for the development of novel π-functional materials. In fact, it afforded n-channel, p-channel, and ambipolar materials, depending on the molecular modification.",

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T2 - Synthesis, structure, and applications

AU - Fukutomi, Yuta

AU - Nakano, Masahiro

AU - Hu, Jian Yong

AU - Osaka, Itaru

AU - Takimiya, Kazuo

PY - 2013/8/7

Y1 - 2013/8/7

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AB - A straightforward synthesis of α,β-unsubstituted and α-halogenated naphtho[2,3-b:6,7-b′]dithiophenediimides (NDTIs) is described. Electrochemical and optical studies of N,N-dioctyl-NDTI demonstrate that the compound has a low-lying LUMO energy level (4.0 eV below the vacuum level) and a small HOMO-LUMO gap (∼2.1 eV). With its interesting electronic and optical properties, in addition to its planar structure, NDTI is a promising building block for the development of novel π-functional materials. In fact, it afforded n-channel, p-channel, and ambipolar materials, depending on the molecular modification.

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Naphthodithiophenediimide (NDTI): Synthesis, structure, and applications

Abstract

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