5,14-Diaryldiindeno[2,1- f:1′,2′ -j]picene: A New Stable [7]Helicene with a Partial Biradical Character

Ya Chu Hsieh, Cheng Feng Wu, Yi Ting Chen, Chia Te Fang, Chi Shin Wang, Chia Hsin Li, Liang Yu Chen, Mu-Jeng Cheng, Chu Chen Chueh, Pi Tai Chou, Yao-Ting Wu

研究成果: Article

8 引文 (Scopus)

摘要

5,14-Diaryldiindeno[2,1-f:1′,2′-j]picene (DDP, 1), a thermally and chemically stable helical arene, can be prepared from 1,4-bis[2-(arylethynyl)phenyl]benzene in four synthetic steps. Its helical backbone, which incorporates an o-quinodimethane moiety, was verified by X-ray crystallography, and this structural feature results in a very high barrier to racemization (exceeding 50 kcal/mol). DDP possesses versatile and promising properties, including a small HOMO-LUMO energy gap (1.31 eV for the dimesityl-substituted derivative 1ab), an electron spin resonance (ESR)-active character, a small triplet-singlet energy gap (4.75 kcal/mol), broad photoabsorption covering the ultraviolet, visible, and near-infrared (NIR) regions, two-photon absorption in the NIR range, and respectable ambipolar charge-transport behavior in a solution-processed organic field-effect transistor.

原文English
期刊Journal of the American Chemical Society
DOIs
出版狀態Accepted/In press - 2018 一月 1

指紋

X Ray Crystallography
Electron Spin Resonance Spectroscopy
Benzene
Photons
Energy gap
Infrared radiation
Organic field effect transistors
X ray crystallography
Paramagnetic resonance
Charge transfer
Derivatives
picene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

引用此文

Hsieh, Ya Chu ; Wu, Cheng Feng ; Chen, Yi Ting ; Fang, Chia Te ; Wang, Chi Shin ; Li, Chia Hsin ; Chen, Liang Yu ; Cheng, Mu-Jeng ; Chueh, Chu Chen ; Chou, Pi Tai ; Wu, Yao-Ting. / 5,14-Diaryldiindeno[2,1- f:1′,2′ -j]picene : A New Stable [7]Helicene with a Partial Biradical Character. 於: Journal of the American Chemical Society. 2018.
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abstract = "5,14-Diaryldiindeno[2,1-f:1′,2′-j]picene (DDP, 1), a thermally and chemically stable helical arene, can be prepared from 1,4-bis[2-(arylethynyl)phenyl]benzene in four synthetic steps. Its helical backbone, which incorporates an o-quinodimethane moiety, was verified by X-ray crystallography, and this structural feature results in a very high barrier to racemization (exceeding 50 kcal/mol). DDP possesses versatile and promising properties, including a small HOMO-LUMO energy gap (1.31 eV for the dimesityl-substituted derivative 1ab), an electron spin resonance (ESR)-active character, a small triplet-singlet energy gap (4.75 kcal/mol), broad photoabsorption covering the ultraviolet, visible, and near-infrared (NIR) regions, two-photon absorption in the NIR range, and respectable ambipolar charge-transport behavior in a solution-processed organic field-effect transistor.",
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5,14-Diaryldiindeno[2,1- f:1′,2′ -j]picene : A New Stable [7]Helicene with a Partial Biradical Character. / Hsieh, Ya Chu; Wu, Cheng Feng; Chen, Yi Ting; Fang, Chia Te; Wang, Chi Shin; Li, Chia Hsin; Chen, Liang Yu; Cheng, Mu-Jeng; Chueh, Chu Chen; Chou, Pi Tai; Wu, Yao-Ting.

於: Journal of the American Chemical Society, 01.01.2018.

研究成果: Article

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T2 - A New Stable [7]Helicene with a Partial Biradical Character

AU - Hsieh, Ya Chu

AU - Wu, Cheng Feng

AU - Chen, Yi Ting

AU - Fang, Chia Te

AU - Wang, Chi Shin

AU - Li, Chia Hsin

AU - Chen, Liang Yu

AU - Cheng, Mu-Jeng

AU - Chueh, Chu Chen

AU - Chou, Pi Tai

AU - Wu, Yao-Ting

PY - 2018/1/1

Y1 - 2018/1/1

N2 - 5,14-Diaryldiindeno[2,1-f:1′,2′-j]picene (DDP, 1), a thermally and chemically stable helical arene, can be prepared from 1,4-bis[2-(arylethynyl)phenyl]benzene in four synthetic steps. Its helical backbone, which incorporates an o-quinodimethane moiety, was verified by X-ray crystallography, and this structural feature results in a very high barrier to racemization (exceeding 50 kcal/mol). DDP possesses versatile and promising properties, including a small HOMO-LUMO energy gap (1.31 eV for the dimesityl-substituted derivative 1ab), an electron spin resonance (ESR)-active character, a small triplet-singlet energy gap (4.75 kcal/mol), broad photoabsorption covering the ultraviolet, visible, and near-infrared (NIR) regions, two-photon absorption in the NIR range, and respectable ambipolar charge-transport behavior in a solution-processed organic field-effect transistor.

AB - 5,14-Diaryldiindeno[2,1-f:1′,2′-j]picene (DDP, 1), a thermally and chemically stable helical arene, can be prepared from 1,4-bis[2-(arylethynyl)phenyl]benzene in four synthetic steps. Its helical backbone, which incorporates an o-quinodimethane moiety, was verified by X-ray crystallography, and this structural feature results in a very high barrier to racemization (exceeding 50 kcal/mol). DDP possesses versatile and promising properties, including a small HOMO-LUMO energy gap (1.31 eV for the dimesityl-substituted derivative 1ab), an electron spin resonance (ESR)-active character, a small triplet-singlet energy gap (4.75 kcal/mol), broad photoabsorption covering the ultraviolet, visible, and near-infrared (NIR) regions, two-photon absorption in the NIR range, and respectable ambipolar charge-transport behavior in a solution-processed organic field-effect transistor.

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