2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores
Autor(a) principal: | |
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Data de Publicação: | 2006 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/1822/7843 |
Resumo: | A series of nonlinear optical chromophores 6 containing a substituted benzothiazole ring have been synthesized and characterized. 1,3-Benzothiazoles 6 were prepared by reacting various formyl derivatives of thienyl compounds with ortho-aminobenzenethiol in fair to excellent yields. These in turn were prepared by Suzuki coupling between aryl and thienyl precursors. The electronic interactions between donor and acceptor end groups in the conjugated 1,3-benzothiazoles 6 are expressed in the intense and markedly solvatochromic CT transitions. The solvatochromic behaviour of compounds 6 was determinated by linear regression analyses of absorption maxima in several solvents, whereby benzothiazole 6f was found to be a very appropriate indicator dye whose absorption wavenumbers (νmax= 1590 cm –1) in aliphatic and dipolar aprotic and in aromatic and chlorinated solvents excellently correlate with the π* values defined by Kamlet and Taft. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. Thermo gravimetric analysis (TGA) was used to evaluate their thermal stability. The experimental results indicate that good nonlinearity–thermal stability is well balanced for chromophores 6, making them good candidates for device applications. |
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2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophoresArylthiophenesBithiophenesAldehydesBenzothiazolesAcceptor substituted oligothiophenesUV/Visible spectroscopyChromophoresSolvatochromismThermal stabilityNonlinear (NLO) opticsHyper-Rayleight ScatteringOptical propertiesUV/Vis spectroscopynonlinear opticsScience & TechnologyA series of nonlinear optical chromophores 6 containing a substituted benzothiazole ring have been synthesized and characterized. 1,3-Benzothiazoles 6 were prepared by reacting various formyl derivatives of thienyl compounds with ortho-aminobenzenethiol in fair to excellent yields. These in turn were prepared by Suzuki coupling between aryl and thienyl precursors. The electronic interactions between donor and acceptor end groups in the conjugated 1,3-benzothiazoles 6 are expressed in the intense and markedly solvatochromic CT transitions. The solvatochromic behaviour of compounds 6 was determinated by linear regression analyses of absorption maxima in several solvents, whereby benzothiazole 6f was found to be a very appropriate indicator dye whose absorption wavenumbers (νmax= 1590 cm –1) in aliphatic and dipolar aprotic and in aromatic and chlorinated solvents excellently correlate with the π* values defined by Kamlet and Taft. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. Thermo gravimetric analysis (TGA) was used to evaluate their thermal stability. The experimental results indicate that good nonlinearity–thermal stability is well balanced for chromophores 6, making them good candidates for device applications.Fundação para a Ciência e TecnologiaWiley-VCH VerlagUniversidade do MinhoCosta, Susana P. G.Batista, Rosa Maria FerreiraCardoso, PauloBelsley, M.Raposo, M. Manuela M.20062006-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/7843eng"European Journal of Organic Chemistry". ISSN 1434-193X. 17 (2006) 3938-3946.1434-193X1099-069010.1002/ejoc.200600059www.interscience.wiley.cominfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:33:14Zoai:repositorium.sdum.uminho.pt:1822/7843Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:28:44.609676Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
title |
2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
spellingShingle |
2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores Costa, Susana P. G. Arylthiophenes Bithiophenes Aldehydes Benzothiazoles Acceptor substituted oligothiophenes UV/Visible spectroscopy Chromophores Solvatochromism Thermal stability Nonlinear (NLO) optics Hyper-Rayleight Scattering Optical properties UV/Vis spectroscopy nonlinear optics Science & Technology |
title_short |
2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
title_full |
2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
title_fullStr |
2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
title_full_unstemmed |
2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
title_sort |
2-arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores |
author |
Costa, Susana P. G. |
author_facet |
Costa, Susana P. G. Batista, Rosa Maria Ferreira Cardoso, Paulo Belsley, M. Raposo, M. Manuela M. |
author_role |
author |
author2 |
Batista, Rosa Maria Ferreira Cardoso, Paulo Belsley, M. Raposo, M. Manuela M. |
author2_role |
author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Costa, Susana P. G. Batista, Rosa Maria Ferreira Cardoso, Paulo Belsley, M. Raposo, M. Manuela M. |
dc.subject.por.fl_str_mv |
Arylthiophenes Bithiophenes Aldehydes Benzothiazoles Acceptor substituted oligothiophenes UV/Visible spectroscopy Chromophores Solvatochromism Thermal stability Nonlinear (NLO) optics Hyper-Rayleight Scattering Optical properties UV/Vis spectroscopy nonlinear optics Science & Technology |
topic |
Arylthiophenes Bithiophenes Aldehydes Benzothiazoles Acceptor substituted oligothiophenes UV/Visible spectroscopy Chromophores Solvatochromism Thermal stability Nonlinear (NLO) optics Hyper-Rayleight Scattering Optical properties UV/Vis spectroscopy nonlinear optics Science & Technology |
description |
A series of nonlinear optical chromophores 6 containing a substituted benzothiazole ring have been synthesized and characterized. 1,3-Benzothiazoles 6 were prepared by reacting various formyl derivatives of thienyl compounds with ortho-aminobenzenethiol in fair to excellent yields. These in turn were prepared by Suzuki coupling between aryl and thienyl precursors. The electronic interactions between donor and acceptor end groups in the conjugated 1,3-benzothiazoles 6 are expressed in the intense and markedly solvatochromic CT transitions. The solvatochromic behaviour of compounds 6 was determinated by linear regression analyses of absorption maxima in several solvents, whereby benzothiazole 6f was found to be a very appropriate indicator dye whose absorption wavenumbers (νmax= 1590 cm –1) in aliphatic and dipolar aprotic and in aromatic and chlorinated solvents excellently correlate with the π* values defined by Kamlet and Taft. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. Thermo gravimetric analysis (TGA) was used to evaluate their thermal stability. The experimental results indicate that good nonlinearity–thermal stability is well balanced for chromophores 6, making them good candidates for device applications. |
publishDate |
2006 |
dc.date.none.fl_str_mv |
2006 2006-01-01T00:00:00Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/1822/7843 |
url |
http://hdl.handle.net/1822/7843 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
"European Journal of Organic Chemistry". ISSN 1434-193X. 17 (2006) 3938-3946. 1434-193X 1099-0690 10.1002/ejoc.200600059 www.interscience.wiley.com |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Wiley-VCH Verlag |
publisher.none.fl_str_mv |
Wiley-VCH Verlag |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799132784369860608 |