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Synthesis, Crystal Structures, Optical Properties, and Photocurrent Response of Heteroacene Derivatives
Author(s) -
Ren Tiejun,
Xiao Jinchong,
Wang Wenying,
Xu Wenya,
Wang Sujuan,
Zhang Xuemin,
Wang Xuefei,
Chen Hua,
Zhao Jianwen,
Jiang Li
Publication year - 2014
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.201402247
Subject(s) - intramolecular force , thiophene , dihedral angle , ether , benzene , monoclinic crystal system , photocurrent , electrochemistry , anthracene , chemistry , crystallography , single crystal , crystal structure , crystal (programming language) , materials science , photochemistry , stereochemistry , molecule , organic chemistry , electrode , hydrogen bond , optoelectronics , computer science , programming language
Six 5,9,14,18‐tetrathiaheptacene derivatives ( 1 a – 1 f ) were synthesized by using a simple ether–ether exchange reaction and fully characterized. In contrast to the planar conformation usually observed in thiophene‐fused benzene systems, single‐crystal analysis indicates that 7,16‐dipropyl‐5,9,14,18‐tetrathiaheptacene ( 1 a ), 7,16‐diphenyl‐5,9,14,18‐tetrathiaheptacene ( 1 b ), and 7,16‐di(4′‐chlorophenyl)‐5,9,14,18‐tetrathiaheptacene ( 1 c ) adopt chair conformations. The as‐formed dihedral angle between anthracene and the terminal benzene units are 137.258, 137.855, and 134.912° for 1 a , 1 b , and 1 c , respectively, which is close to the theoretical optimization results (128° for 1 b ). Interestingly, the oxidized product of 7,16‐di(trifluoromethylphenyl)‐5,9,14,18‐tetrathiaheptacene ( 1 e ) has a saddle shape, which results in the formation of column‐shaped units in the single crystal. The substituents on the side phenyl group have less effect on their UV/Vis absorption spectra, but a distinct redshift that accounts for the intramolecular charge transfer can be observed in the emission spectra. The electrochemical measurements show that all compounds present two oxidation waves. The photoswitching behavior based on 1 a–1 f was further measured and the experimental results suggest that these heteroacene derivatives are promising semiconductor materials for organic electronics.