Optical, redox, and NLO properties of tricyanovinyl oligothiophenes: comparisons between symmetric and asymmetric substitution patterns

Chemistry : a European Journal
Juan CasadoBelén Villacampa

Abstract

A series of tricyanovinyl (TCV)-substituted oligothiophenes was synthesized and investigated with a number of physical methods including UV/Vis, IR, and Raman spectroscopy, nonlinear optical (NLO) measurements, X-ray diffraction, and cyclic voltammetry. Mono- or disubstituted oligomers were prepared by the reaction of tetracyanoethylene with mono- or dilithiated oligomers. The comparative effects of the symmetric and asymmetric substitutions in the electronic and molecular properties have been addressed. These oligomers display dramatic reductions in both their optical and electrochemical band gaps in comparison with unsubstituted molecules. The analysis of the electronic properties of the molecules was assisted by density functional theory calculations, which are in excellent agreement with the experimental data. TCV substitution influences the energies of the frontier orbitals, especially with respect to the stabilization of LUMO orbitals. X-ray structural characterization of a monosubstituted oligomer exhibits pi-stacking with favorable intermolecular interactions. NLO results agree with the role of the intramolecular charge-transfer feature in the asymmetric samples. These results furthermore exalt the role of conformationa...Continue Reading

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Citations

Dec 13, 2006·Beilstein Journal of Organic Chemistry·Grigoriy SeredaNicole Collins
Nov 26, 2009·Chemistry : a European Journal·Rocío Ponce OrtizTetsuo Otsubo
Oct 20, 2011·Chemical Society Reviews·Anastasia B S ElliottKeith C Gordon
Jun 19, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Raquel AndreuJesús Orduna
Jan 11, 2020·Physical Chemistry Chemical Physics : PCCP·Christian RotheSabine Ludwigs
Sep 18, 2009·The Journal of Physical Chemistry. a·Adam S HussDavid A Blank
Aug 29, 2009·The Journal of Organic Chemistry·Chunyan DuGui Yu
Aug 9, 2011·The Journal of Physical Chemistry. B·Sandra Rodríguez GonzálezJuan Casado
Aug 14, 2021·Physical Chemistry Chemical Physics : PCCP·Ana González MorenoAbel de Cózar
Sep 26, 2006·The Journal of Organic Chemistry·María Moreno OlivaJuan T López Navarrete

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