Tetrathiafulvalene Derivatives as NLO-phores: Synthesis, Electrochemistry, Raman Spectroscopy, Theoretical Calculations, and NLO Properties of Novel TTF-Derived Donor-π-Acceptor Dyads
- 30 November 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (26) , 8872-8882
- https://doi.org/10.1021/jo010717k
Abstract
Novel π-conjugated donor−acceptor chromophores, based on the strong electron-donating tetrathiafulvalene moiety and different electron-withdrawing acceptors, exhibit large second-order optical nonlinearities. The effect of increasing the length of the polyenic spacer and the influence of the nature of the acceptor moiety on the NLO properties have been studied by using the electric field-induced second-harmonic generation (EFISH) technique as well as by semiempirical and ab initio theoretical calculations. A charge-transfer band has been observed in the absorption spectra of these D-π-A compounds that undergoes an hypsochromic shift when increasing the number of vinylenic spacer units connecting both donor and acceptor moieties. The degree of the intramolecular charge transfer from the donor to the acceptor has also been analyzed by means of Raman spectroscopy.This publication has 77 references indexed in Scilit:
- Nonlinear Optics for High-Speed Digital Information ProcessingScience, 1999
- Donor-π-Acceptor Species Derived from Functionalised 1,3-Dithiol-2-ylidene Anthracene Donor Units Exhibiting Photoinduced Electron Transfer Properties: Spectroscopic, Electrochemical, X-Ray Crystallographic and Theoretical StudiesChemistry – A European Journal, 1998
- Organic and polymeric nonlinear optical materials: introductionJournal of the Optical Society of America B, 1998
- 1,3-Bis(dicyanomethylidene)indane-Based Second-Order NLO MaterialsChemistry of Materials, 1996
- Improved Syntheses of Carboxytetrathiafulvalene, Formyltetrathiafulvalene and (Hydroxymethyl)tetrathiafulvalene1: Versatile Building Blocks for New Functionalised Tetrathiafulvalene DerivativesSynthesis, 1994
- Ab initio time-dependent coupled perturbed Hartree-Fock studies of optical nonlinearities of organic molecules: alkyl derivatives of 4-amino-.beta.-nitrostyreneThe Journal of Physical Chemistry, 1993
- Studies on π-acceptor molecules containing the dicyanomethylene group. X-Ray crystal structure of the charge-transfer complex of tetramethyltetrathiafulvalene and 2,3-dicyano-1,4-naphthoquinone: (TMTTF)3–(DCNQ)2Journal of the Chemical Society, Perkin Transactions 2, 1993
- Electronic structure and nonlinear optical properties of push-pull polyenes: theoretical investigation of benzodithia polyenals and dithiolene polyenalsJournal of the American Chemical Society, 1992
- Length dependence of the second-order optical nonlinearity in conjugated hydrocarbonsThe Journal of Chemical Physics, 1981
- Über ungesättigte Aldehyde und Ketone, II. Eine neue Reaktion magnesium‐(lithium‐)organischer VerbindungenEuropean Journal of Inorganic Chemistry, 1958