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Charge Transfer Through Dithieno[2,3‐ a :3′,2′‐ c ]phenazine: Effect of Substitution Pattern on the Optoelectronic Properties of Regioisomeric Luminophores
Author(s) -
Chen Yijing,
Lu Xuefeng,
Xiang Chunlan,
Ling Yuan,
Zhou Gang
Publication year - 2016
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.201501389
Subject(s) - intramolecular force , luminophore , phenazine , substitution (logic) , chemistry , structural isomer , crystallography , acceptor , photoluminescence , band gap , stereochemistry , photochemistry , luminescence , materials science , optoelectronics , organic chemistry , physics , computer science , programming language , condensed matter physics
Abstract Two series of regioisomeric luminophores that contained a dithieno[2,3‐ a :3′,2′‐ c ]phenazine (DTP) unit as an electron acceptor have been designed and synthesized. To investigate the effect of substitution pattern on the optoelectronic properties of these luminophores, electron donors ( N , N ‐dihexylaniline or N , N ‐dihexyl‐4‐vinylaniline) were incorporated at the 2,5‐, 8,11‐, and 9,10‐positions of the DTP unit. We found that the optoelectronic properties of the regioisomeric luminophores were greatly affected by the substitution pattern: functionalization at the 8,11‐positions of the DTP unit was superior to the other two substitution patterns in extending the effective π‐conjugation and strengthening the intramolecular charge‐transfer interactions. Moreover, the insertion of vinyl groups between the DTP and N , N ‐dihexylaniline units narrowed the energy band‐gap for isomers 4 and 5 . However, hypsochromically shifted absorption and photoluminescence maxima were observed for isomeric luminophore 6 , in which electron donors were substituted at the 2,5‐positions of the DTP unit. These results should facilitate greater understanding of the structure–property relationships in regioisomeric semiconductors and present a new way to design optoelectronic materials with effective substitution patterns.