Title
Asymmetrically substituted distyrylbenzenes and their polar crystal structures Asymmetrically substituted distyrylbenzenes and their polar crystal structures
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Montrouge ,
Subject
Chemistry
Source (journal)
New journal of chemistry. - Montrouge
Volume/pages
35(2011) :3 , p. 649-662
ISSN
1144-0546
ISI
000287867300019
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
The synthesis of twelve asymmetric donoracceptor distyrylbenzene derivatives with either one nitrile group or one, two or three nitro groups as electron acceptors, and one, two or three methoxy groups as electron donors is reported. Peak potentials obtained from cyclic voltammetry were combined with experimental UV/Vis data and molecular dipole moments obtained from quantum chemical calculations, yielding insight into the influence of the positions of the substituents on the electronic structure and charge distribution of this as yet unexplored class of organic semiconductors. The supramolecular structures of five of these compounds have been studied using single-crystal X-ray diffraction to monitor the influence of the positions of donor and acceptor groups on the organisation of the molecules in the solid state, and three crystal structures have been identified in which the molecular dipoles do not organize themselves in a centrosymmetric lattice. Analysis of the dipoles in the unit cell yields further insight into the possible non-linear optical properties of these three polar structures.
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