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Pechmann Dye‐Based Molecules Containing Fluorobenzene Moieties for Ambipolar Organic Semiconductors
Author(s) -
Luo Hewei,
Dong Xiaobiao,
Cai Zhengxu,
Wang Lizhen,
Liu Zitong
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.201700669
Subject(s) - chemistry , ambipolar diffusion , moiety , acceptor , organic field effect transistor , molecule , electron acceptor , fluorobenzene , triphenylamine , thiophene , electron mobility , electron donor , crystallography , photochemistry , stereochemistry , electron , organic chemistry , field effect transistor , transistor , materials science , physics , benzene , optoelectronics , quantum mechanics , voltage , catalysis , condensed matter physics
Two hybrid A 2 ‐D‐A 1 ‐D‐A 2 (A=acceptor, D=donor) molecules, that is, ( E )‐5,5′‐bis[5‐(4‐fluorophenyl)thiophen‐2‐yl]‐1,1′‐dioctyl‐[3,3′‐bipyrrolylidene]‐2,2′(1 H ,1′ H )‐dione ( FBBPD ) and ( E )‐1,1′‐dioctyl‐5,5′‐bis[5‐(3,4,5‐trifluorophenyl)thiophen‐2‐yl]‐[3,3′‐bipyrrolylidene]‐2,2′(1 H ,1′ H )‐dione ( TFBBPD ), were synthesized and characterized. Each of these compounds contain the Pechmann dye derivative ( E )‐[3,3′‐bipyrrolylidene]‐2,2′(1 H ,1′ H )‐dione ( BPD ) as the electron‐accepting core, which is flanked by an electron‐donor moiety (i.e., thiophene) and other electron acceptors (i.e., 4‐fluorobenzene or 3,4,5‐trifluorobenzene). Organic field‐effect transistor (OFET) results of FBBPD show ambipolar properties with electron ( μ e max ) and hole mobilities ( μ h max ) up to 0.20 and 0.023 cm 2 V −1 s −1 , respectively. In comparison, the electron and hole mobilities of the OFET based on TFBBPD , which contains a more electron‐accepting moiety, are higher ( μ e max =0.58 cm 2 V −1 s −1 and μ h max =0.054 cm 2 V −1 s −1 ). X‐ray diffraction and atomic force microscopy studies were carried out to investigate the variations in the mobilities. Overall, these studies show the potential of BPD in hybrid D‐A molecules to act as the electron‐acceptor moiety in organic semiconducting studies.