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https://hdl.handle.net/1822/33539
Título: | Structure-property relationships in push-pull amino/cyanovinyl end-capped oligothiophenes : quantum chemical and experimental studies |
Autor(es): | Oliva, María Moreno Casado, Juan Raposo, M. Manuela M. Fonseca, A. Maurício C. Hartmann, Horst Hernández, Víctor Navarrete, Juan T. López |
Palavras-chave: | Thiophene Push-pull oligomers Dicyanovinyl heterocycles Electronic structure DFT calculations Electrochemical properties Nonlinear optical (NLO) materials Oligothiophenes |
Data: | 2006 |
Editora: | American Chemical Society |
Revista: | J. Org. Chem. |
Citação: | J. Org. Chem., 2006, 71(20), 7509-7520. |
Resumo(s): | A series of push-pull chromophores built around thiophene-based π-conjugating spacers and bearing various types of amino-donors and cyanovinyl-acceptors have been analysed by means of UV-Vis-NIR, IR and Raman spectroscopic measurements in the solid state as well as in solution. The intramolecular charge transfer (ICT) of these π-conjugated systems has also been tested by analysing the ability of the solute molecules in undergoing shifts in their fluorescence emission maxima with increasing solvent polarity. These push-pull oligomers also display an attractive electrochemical behaviour since they generate stable species both upon oxidation and reduction. Oxidation mainly involves changes in the electron-rich aminooligothienyl half-part of the molecule and leads to the formation of stable cations. On the other hand, reduction to radical anions and dianions is mainly cyanovinyl-centered but also affects the π-conjugated electron-relay. Density functional theory (DFT) calculations have been carried out to help the assignment of the most relevant electronic and vibrational features and to derive useful information about the molecular structure of these NLO-phores. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/33539 |
DOI: | 10.1021/jo060318v |
ISSN: | 0022-3263 1520-6904 |
Arbitragem científica: | yes |
Acesso: | Acesso restrito UMinho |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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JOC 2006.pdf Acesso restrito! | Documento principal | 459,74 kB | Adobe PDF | Ver/Abrir |
joc sup. inf. 2006.pdf Acesso restrito! | Supporting information | 105,71 kB | Adobe PDF | Ver/Abrir |