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Structural and Electronic Properties of Crystalline, Isomerically Pure Anthradithiophene Derivatives
Author(s) -
Hallani Rawad K.,
Thorley Karl J.,
Mei Yaochuan,
Parkin Sean R.,
Jurchescu Oana D.,
Anthony John E.
Publication year - 2016
Publication title -
advanced functional materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 6.069
H-Index - 322
eISSN - 1616-3028
pISSN - 1616-301X
DOI - 10.1002/adfm.201502440
Subject(s) - materials science , chromophore , intermolecular force , homogeneous , yield (engineering) , organic semiconductor , molecule , organic chemistry , thermodynamics , optoelectronics , chemistry , physics , metallurgy
Anthradithiophene chromophores are found in many current high‐performance organic semiconductors, even though these materials are typically synthesized as an inseparable mixture of syn and anti isomers. Recent syntheses of pure syn anthradithiophenes have shown no improvement in performance for the more homogeneous system, but similar studies on the pure anti isomer have not been reported. In this work, a simple protocol is described to prepare the pure anti isomer of fluorinated, functionalized anthradithiophenes, and perform detailed analysis of the intermolecular interactions in the crystal that yield increased density and closer chromophore contacts. Studies of the charge‐transport properties of these pure isomers, compared to the isomeric mixtures, suggest that the benefit of isomer purity is not consistent; in the syn case, there was minimal difference between the pure isomer and the mixture, while for the anti isomer mobility improved nearly twofold. Analysis of disorder in the crystals suggests a reason for this difference in performance.