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Acenequinocumulenes: Lateral and Vertical π‐Extended Analogues of Tetracyanoquinodimethane (TCNQ)
Author(s) -
Gruber Marco,
Padberg Kevin,
Min Jie,
Waterloo Andreas R.,
Hampel Frank,
Maid Harald,
Ameri Tayebeh,
Brabec Christoph J.,
Tykwinski Rik R.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704314
Subject(s) - acene , tetracyanoquinodimethane , cumulene , delocalized electron , molecule , cyclic voltammetry , spectroscopy , materials science , organic semiconductor , crystallography , chemistry , chemical physics , optoelectronics , organic chemistry , physics , electrode , quantum mechanics , electrochemistry
We have designed a series of molecules and developed synthetic methodology that allows for the inclusion of structural diversity along both the lateral and vertical axes of the basic TCNQ skeleton. In the lateral direction, benzoannulation extends the π‐system through (hetero)acene formation, whereas incorporation of a [3]cumulene increases delocalization vertically. The potential of these new molecules as semiconductors is explored through UV/Vis spectroscopy, cyclic voltammetry, X‐ray crystallography, thin‐film formation, and mobility measurements (using space charge limited current measurements).