Dithiophene-fused tetracyanonaphthoquinodimethanes (DT-TNAPs): Synthesis and characterization of π-extended quinoidal compounds for n-channel organic semiconductor

Naoyuki Yanai; Takamichi Mori; Shoji Shinamura; Itaru Osaka; Kazuo Takimiya

doi:10.1021/ol403234q

Dithiophene-fused tetracyanonaphthoquinodimethanes (DT-TNAPs): Synthesis and characterization of π-extended quinoidal compounds for n-channel organic semiconductor

Naoyuki Yanai, Takamichi Mori, Shoji Shinamura, Itaru Osaka, Kazuo Takimiya

SCI - Chemistry

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

22 Citations (Scopus)

Abstract

Dithiophene-fused tetracyanonaphthoquinodimethanes (DTTNAPs) were synthesized and evaluated as n-channel organic semiconductors. DTTNAPs, regardless of isomeric structures and substituents, have low-lying LUMO energy levels (∼4.6 eV below the vacuum level), suitable for stable n-channel field-effect transistors (FETs) under ambient conditions. In fact, α-DTTNAP derivatives afforded solution-processed FETs showing an electron mobility of 10^-3 cm² V^-1 s^-1, indicating that DTTNAPs are a potential molecular framework for n-channel organic semiconductors.

Original language	English
Pages (from-to)	240-243
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	1
DOIs	https://doi.org/10.1021/ol403234q
Publication status	Published - 2014 Jan 3

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abstract = "Dithiophene-fused tetracyanonaphthoquinodimethanes (DTTNAPs) were synthesized and evaluated as n-channel organic semiconductors. DTTNAPs, regardless of isomeric structures and substituents, have low-lying LUMO energy levels (∼4.6 eV below the vacuum level), suitable for stable n-channel field-effect transistors (FETs) under ambient conditions. In fact, α-DTTNAP derivatives afforded solution-processed FETs showing an electron mobility of 10-3 cm2 V-1 s-1, indicating that DTTNAPs are a potential molecular framework for n-channel organic semiconductors.",

author = "Naoyuki Yanai and Takamichi Mori and Shoji Shinamura and Itaru Osaka and Kazuo Takimiya",

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T1 - Dithiophene-fused tetracyanonaphthoquinodimethanes (DT-TNAPs)

T2 - Synthesis and characterization of π-extended quinoidal compounds for n-channel organic semiconductor

AU - Yanai, Naoyuki

AU - Mori, Takamichi

AU - Shinamura, Shoji

AU - Osaka, Itaru

AU - Takimiya, Kazuo

PY - 2014/1/3

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N2 - Dithiophene-fused tetracyanonaphthoquinodimethanes (DTTNAPs) were synthesized and evaluated as n-channel organic semiconductors. DTTNAPs, regardless of isomeric structures and substituents, have low-lying LUMO energy levels (∼4.6 eV below the vacuum level), suitable for stable n-channel field-effect transistors (FETs) under ambient conditions. In fact, α-DTTNAP derivatives afforded solution-processed FETs showing an electron mobility of 10-3 cm2 V-1 s-1, indicating that DTTNAPs are a potential molecular framework for n-channel organic semiconductors.

AB - Dithiophene-fused tetracyanonaphthoquinodimethanes (DTTNAPs) were synthesized and evaluated as n-channel organic semiconductors. DTTNAPs, regardless of isomeric structures and substituents, have low-lying LUMO energy levels (∼4.6 eV below the vacuum level), suitable for stable n-channel field-effect transistors (FETs) under ambient conditions. In fact, α-DTTNAP derivatives afforded solution-processed FETs showing an electron mobility of 10-3 cm2 V-1 s-1, indicating that DTTNAPs are a potential molecular framework for n-channel organic semiconductors.

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Dithiophene-fused tetracyanonaphthoquinodimethanes (DT-TNAPs): Synthesis and characterization of π-extended quinoidal compounds for n-channel organic semiconductor

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