Acenequinocumulenes: Lateral and Vertical π‐Extended Analogues of Tetracyanoquinodimethane (TCNQ). Issue 70 (20th November 2017)

• Record Type: Journal Article
• Authors: Gruber, Marco; Padberg, Kevin; Min, Jie; Waterloo, Andreas R.; Hampel, Frank; Maid, Harald; Ameri, Tayebeh; Brabec, Christoph J.; Tykwinski, Rik R.
• Is Part Of: Chemistry. Volume 23:Issue 70(2017)
• Page Start: 17829
• Page End: 17835
• Publication Date: 2017-11-20
• Subjects: cumulenes -- donor–acceptor systems -- organic materials -- pentacenes -- synthetic methodology; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201704314
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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 basicTCNQ 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). Abstract : Wings of a butterfly : New synthetic methodology extends the basic skeleton of tetracyanoquinodimethane (TCNQ ) along both the lateral and vertical axes, through benzoannulation and incorporation of a [3]cumulene, respectively. Terminal functionalization of the cumulenic core allows attachment of electron donor and acceptor functional groups.