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Unilaterally Fluorinated Acenes: Synthesis and Solid‐State Properties
Author(s) -
Hofmann Philipp E.,
Tripp Matthias W.,
Bischof Daniel,
Grell Yvonne,
Schiller Anna L. C.,
Breuer Tobias,
Ivlev Sergei I.,
Witte Gregor,
Koert Ulrich
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202006489
Subject(s) - pentacene , sublimation (psychology) , molecule , organic semiconductor , chemistry , chemical physics , exciton , surface modification , acene , spectroscopy , electronic structure , semiconductor , materials science , nanotechnology , computational chemistry , organic chemistry , optoelectronics , psychology , physics , quantum mechanics , psychotherapist , thin film transistor , electrode
The rapid development of organic electronics is closely related to the availability of molecular materials with specific electronic properties. Here, we introduce a novel synthetic route enabling a unilateral functionalization of acenes along their long side, which is demonstrated by the synthesis of 1,2,10,11,12,14‐hexafluoropentacene ( 1 ) and the related 1,2,9,10,11‐pentafluorotetracene ( 2 ). Quantum chemical DFT calculations in combination with optical and X‐ray absorption spectroscopy data indicate that the single‐molecule properties of 1 are a connecting link between the organic semiconductor model systems pentacene (PEN) and perfluoropentacene (PFP). In contrast, the crystal structure analysis reveals a different packing motif than for the parent molecules. This can be related to distinct F⋅⋅⋅H interactions identified in the corresponding Hirshfeld surface analysis and also affects solid‐state properties such as the exciton binding energy and the sublimation enthalpy.