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Anthracene−Pentacene Dyads: Synthesis and OFET Characterization
Author(s) -
Hauschild Miriam,
Chen Lan,
Etschel Sebastian H.,
Ferguson Michael J.,
Hampel Frank,
Halik Marcus,
Tykwinski Rik R.
Publication year - 2020
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000233
Subject(s) - pentacene , anthracene , organic field effect transistor , characterization (materials science) , chemistry , photochemistry , nanotechnology , materials science , combinatorial chemistry , physics , transistor , voltage , quantum mechanics , field effect transistor , thin film transistor , layer (electronics)
The synthesis of a series of unsymmetrical derivatives of pentacene appended with functionalized anthracene moieties is reported. These anthracene−pentacene dyads have been characterized by UV‐vis spectroscopy and cyclic voltammetry to examine their electronic properties. X‐ray crystallographic analysis was used to examine the solid‐state features of anthracene−pentacene dyads 1 a – d with H−, F−, Cl−, and Br− substituents on the 9‐position of anthracene, and shows that the packing arrangement of anthracene−pentacene derivatives 1 b,d,e are remarkably similar irrespective of the presence of fluoride, bromide or methyl substituents. The pentacene−anthracene dyads have been incorporated into OTFTs to evaluate their semiconducting properties. The pentacene derivative 1 b shows ambipolar behavior using AlO x C 14 PA as the gate dielectric (electron and hole mobilities of 7.6 ⋅ 10 −3 and 1.6 ⋅ 10 −1 cm 2 V −1 s −1 ), while performance of all derivatives was poor using p‐doped Silicon as the substrate. These studies highlight the importance of thin‐film formation over molecular structure.