TY - JOUR
T1 - 5,14-Diaryldiindeno[2,1- f:1′,2′ -j]picene
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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U2 - 10.1021/jacs.8b08840
DO - 10.1021/jacs.8b08840
M3 - Article
C2 - 30346739
AN - SCOPUS:85055624633
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
ER -