Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties
Autor(a) principal: | |
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Data de Publicação: | 2005 |
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/1822/7846 |
Resumo: | Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 using TCNE. The tricyanovinyl- derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. The β values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties. |
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Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical propertiesPyrrolesThiophenesDonor-acceptor thienylpyrrolesTricyanovinylationChromophoresSolvatochromismElectrochemistryHyper-Rayleigh scattering (HRS)Non-linear optical (NLO) materialchromephoresScience & TechnologyTricyanovinyl-substituted 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 using TCNE. The tricyanovinyl- derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. The β values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties.Fundação para a Ciência e Tecnologia (FCT) - POCTI, FEDER (ref.POCTI/QUI/37816/2001).ElsevierUniversidade do MinhoRaposo, M. Manuela M.Sousa, Ana M. R. C.Kirsch, G.Ferreira, F.Belsley, M.Gomes, E. MatosFonseca, A. Maurício C.20052005-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/7846eng"Tetrahedron". ISSN 0040-4020. 61:50 (Dec. 2005) 11991-11998.0040-402010.1016/j.tet.2005.09.062http://www.sciencedirect.com/science/journal/00404020info: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:RCAAP2023-07-21T12:40:09Zoai:repositorium.sdum.uminho.pt:1822/7846Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:36:54.236906Repositório 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 |
Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties |
title |
Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties |
spellingShingle |
Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties Raposo, M. Manuela M. Pyrroles Thiophenes Donor-acceptor thienylpyrroles Tricyanovinylation Chromophores Solvatochromism Electrochemistry Hyper-Rayleigh scattering (HRS) Non-linear optical (NLO) material chromephores Science & Technology |
title_short |
Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties |
title_full |
Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties |
title_fullStr |
Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties |
title_full_unstemmed |
Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties |
title_sort |
Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties |
author |
Raposo, M. Manuela M. |
author_facet |
Raposo, M. Manuela M. Sousa, Ana M. R. C. Kirsch, G. Ferreira, F. Belsley, M. Gomes, E. Matos Fonseca, A. Maurício C. |
author_role |
author |
author2 |
Sousa, Ana M. R. C. Kirsch, G. Ferreira, F. Belsley, M. Gomes, E. Matos Fonseca, A. Maurício C. |
author2_role |
author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Raposo, M. Manuela M. Sousa, Ana M. R. C. Kirsch, G. Ferreira, F. Belsley, M. Gomes, E. Matos Fonseca, A. Maurício C. |
dc.subject.por.fl_str_mv |
Pyrroles Thiophenes Donor-acceptor thienylpyrroles Tricyanovinylation Chromophores Solvatochromism Electrochemistry Hyper-Rayleigh scattering (HRS) Non-linear optical (NLO) material chromephores Science & Technology |
topic |
Pyrroles Thiophenes Donor-acceptor thienylpyrroles Tricyanovinylation Chromophores Solvatochromism Electrochemistry Hyper-Rayleigh scattering (HRS) Non-linear optical (NLO) material chromephores Science & Technology |
description |
Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 using TCNE. The tricyanovinyl- derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. The β values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties. |
publishDate |
2005 |
dc.date.none.fl_str_mv |
2005 2005-01-01T00:00:00Z |
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/1822/7846 |
url |
http://hdl.handle.net/1822/7846 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
"Tetrahedron". ISSN 0040-4020. 61:50 (Dec. 2005) 11991-11998. 0040-4020 10.1016/j.tet.2005.09.062 http://www.sciencedirect.com/science/journal/00404020 |
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 |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
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 |
repository.mail.fl_str_mv |
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1799132899940761600 |