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https://hdl.handle.net/1822/14627
Título: | Design, synthesis and characterization of the electrochemical, nonlinear optical properties and theoretical studies of novel thienylpyrrole azo dyes bearing benzothiazole acceptor groups |
Autor(es): | Raposo, M. Manuela M. Castro, M. Cidália R. Fonseca, A. Maurício C. Schellenberg, Peter Michael Belsley, M. |
Palavras-chave: | Heterocyclic azo dyes Thienylpyrrole Benzothiazole Push-pull systems Reverse polarity First hyperpolarizability (β) Hyper-Rayleigh scattering (HRS) Redox properties Density functional theory (DFT) Thermal stability Nonlinear optical (NLO) materials First hyperpolarizability (beta) Thienylpyrroles as auxiliary donors |
Data: | Jul-2011 |
Editora: | Elsevier |
Revista: | Tetrahedron |
Resumo(s): | Two series of related donor-acceptor conjugated heterocyclic azo dyes based on the thienylpyrrole system, functionalized with benzothiazol-2-yl (5-6) or benzothiazol-6-yl acceptor groups (7) through an N=N bridge, have been synthesized by azo coupling using 1-alkyl(aryl)thienylpyrroles (1) and benzothiazolyl diazonium salts (2-4) as coupling components. Their optical (linear and first hyperpolarizability), electrochemical and thermal properties have been examined. Optimized ground-state molecular geometries and estimates of the lowest energy single electron vertical excitation energies in dioxane solutions were obtained using density functional theory (DFT) at the B3LYP/6-31+G(d,p) level. Hyper-Rayleigh scattering (HRS) in dioxane solutions using a fundamental wavelength of 1064 nm was employed to evaluate their second-order nonlinear optical properties. Of these systems, the benzothiazol-2-yl-diazenes 5-6 exhibit the largest first hyperpolarizabilities ( = 460 - 660 x 10-30 esu, T convention) compared to benzothiazol-6-yl-diazenes 7 ( = 360 - 485 x 10-30 esu, T convention). Good to excellent thermal stabilities were also obtained for all azo dyes (235 - 317 oC). This multidisciplinary study showed that modulation of the optical and electronic properties can be achieved by introduction of the benzothiazole acceptor group in the thienylpyrrole system through position 2 or 6 of the benzothiazole heterocycle. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/14627 |
DOI: | 10.1016/j.tet.2011.05.053 |
ISSN: | 0040-4020 |
Versão da editora: | www.sciencedirect.com |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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Design, synthesis and characterization of the electrochemical, nonlinear optical.pdf | 822,2 kB | Adobe PDF | Ver/Abrir |