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Hepta‐thienoacenes with Internal Carbazole: Synthesis, Regioselectivities and Organic Field‐Effect Transistor Applications
Author(s) -
Hu Yueming,
Wang Hao,
Liu Shuli,
Zhang Jing,
Zhao Baomin,
Fu Nina,
Yi Mingdong,
Huang Wei
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800368
Subject(s) - carbazole , chemistry , thermogravimetric analysis , tandem , differential scanning calorimetry , electron mobility , photoluminescence , field effect transistor , regioselectivity , organic semiconductor , cyclic voltammetry , analytical chemistry (journal) , transistor , optoelectronics , photochemistry , organic chemistry , materials science , electrochemistry , electrode , catalysis , physics , quantum mechanics , voltage , composite material , thermodynamics
Acenes/heteroacenes, the most widely studied small‐molecule organic semiconductors, always possess linear structures. In this work, three stable, soluble and angular π‐extended hepta‐thienoacenes with an internal carbazole, that is, thienobenzo‐fused carbazole ( DTBCz ) were synthesized via a four‐step tandem method. The tandem synthesis starting from carbazole derivatives led to interesting isomeric effects. The synthetic regioselectivity was discussed in detail. Their physical properties and electron density distributions were studied by UV/Vis absorption, photoluminescence, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltammetry (CV) measurements, and theoretical calculations. Their potentials as semiconducting materials were evaluated by fabricating the solution‐processed organic field‐effect transistors (OFETs). The more angular shaped isomer of DTB[32,34]Cz displayed the best performance with hole mobility up to 0.0044 cm 2 V −1 s −1 in devices with a thickness of ca. 115 nm. Particularly, the performance of DTB[32,34]Cz ‐based devices showed less dependence on the thickness of their active layer.