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Synthesis, Characterization, and Physical Properties of a Conjugated Heteroacene: 2‐Methyl‐1,4,6,7,8,9‐hexaphenylbenz( g )isoquinolin‐3(2 H )‐one (BIQ)
Author(s) -
Zhang Qichun,
Xiao Jinchong,
Yin Zongyou,
Duong Hieu M.,
Qiao Fen,
Boey Freddy,
Hu Xiao,
Zhang Hua,
Wudl Fred
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000659
Subject(s) - photobleaching , pentacene , organic semiconductor , conjugated system , electron acceptor , chemistry , heterojunction , characterization (materials science) , organic solar cell , absorption (acoustics) , acceptor , materials science , photochemistry , optoelectronics , organic chemistry , nanotechnology , polymer , physics , layer (electronics) , quantum mechanics , composite material , fluorescence , condensed matter physics , thin film transistor
We report the synthesis and characterization of a novel, stable and blue heteroacene, 2‐methyl‐1,4,6,7,8,9‐hexaphenylbenz( g )isoquinolin‐3(2 H )‐one (BIQ 3 ). BIQ 3 , with its relatively small π framework, has an absorption λ max at 620 nm, which is larger than that of pentacene ( λ max =582 nm), but BIQ 3 is more stable. The solutions of BIQ 3 are observed without any noticeable photobleaching on the order of days. In the solid state, it is very stable at ambient conditions and can be stored indefinitely. Owing to its pyridone end unit, BIQ 3 can display different resonance structures in different solvents (aprotic and protic) or Lewis acids to give different colors. The attractive stability exhibited by BIQ 3 is very desirable in organic semiconductor devices. Herein, we investigated a simple heterojunction photovoltaic device based on BIQ 3 as an electron donor and [6,6]‐phenyl‐C 61 butyric methyl ester as an electron acceptor. Our results show that this type of heteroacene could be a good candidate as a charge‐transport material in organic semiconductor devices.