Acenequinocumulenes: Lateral and Vertical [pi]-Extended Analogues of Tetracyanoquinodimethane (TCNQ)

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, wherea...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-12, Vol.23 (70), p.17829
Main Authors: Gruber, Marco, Padberg, Kevin, Min, Jie, Waterloo, Andreas R, Hampel, Frank, Maid, Harald, Ameri, Tayebeh, Brabec, Christoph J, Tykwinski, Rik R
Format: Article
Language:English
Subjects:
Chemistry
Crystallography
Electronics industry
Space charge
Spectroscopy
Tetracyanoquinodimethane
Thin films
X-ray crystallography
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Summary: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).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201704314