Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials
Autor(a) principal: | |
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Data de Publicação: | 2014 |
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/1822/32116 |
Resumo: | The demand for dyes with solvatochromic properties has increased in the last few years, mainly due to their wide range of applications in the analytical and industrial fields, such as in the textile industry. The phenomenon of solvatochromism is associated with the differential solvation of the ground and excited states of the solvatochromic compounds, leading to an important tool for the study of the nature of solute–solvent interactions. In this paper we report the synthesis of new bis(indolyl)methane derivatives bearing arylthiophene spacers (2a–d) functionalized with electron-donating and electron- withdrawing groups, and the photophysical studies in different solvents, such as ethanol, acetonitrile, dichloromethane, trichloromethane, dimethylsulfoxide, diethylether and 1,4-dioxane. Aiming to explore their solvatochromic behavior in the ground and excited states, all solvents employed have different hydrogen-bond donor abilities. The largest colour modifications were visualized for compound 2b, the solution colours of which are orange in DMSO, blue in trichloromethane, green in dichloromethane and purple in 1,4-dioxane. A negative solvatochromism was observed in 2b and positive one in 2a, 2c and 2d. |
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Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materialsBis-indolylmethanesSolvatochromismSynthesisHeterocyclesThiophenePyrroleUV-visible spectroscopyArylthiophene pi-bridgesCiências Naturais::Ciências QuímicasScience & TechnologyThe demand for dyes with solvatochromic properties has increased in the last few years, mainly due to their wide range of applications in the analytical and industrial fields, such as in the textile industry. The phenomenon of solvatochromism is associated with the differential solvation of the ground and excited states of the solvatochromic compounds, leading to an important tool for the study of the nature of solute–solvent interactions. In this paper we report the synthesis of new bis(indolyl)methane derivatives bearing arylthiophene spacers (2a–d) functionalized with electron-donating and electron- withdrawing groups, and the photophysical studies in different solvents, such as ethanol, acetonitrile, dichloromethane, trichloromethane, dimethylsulfoxide, diethylether and 1,4-dioxane. Aiming to explore their solvatochromic behavior in the ground and excited states, all solvents employed have different hydrogen-bond donor abilities. The largest colour modifications were visualized for compound 2b, the solution colours of which are orange in DMSO, blue in trichloromethane, green in dichloromethane and purple in 1,4-dioxane. A negative solvatochromism was observed in 2b and positive one in 2a, 2c and 2d.Fundação para a Ciência e a Tecnologia (FCT)Royal Society of ChemistryUniversidade do MinhoOliveira, Elisabete J.Batista, Rosa Maria FerreiraCosta, Susana P. G.Raposo, M. Manuela M.Lodeiro, Carlos20142014-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/32116eng1474-905X10.1039/C3PP50352Finfo: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:RCAAP2023-07-21T12:03:15Zoai:repositorium.sdum.uminho.pt:1822/32116Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T18:53:21.063202Repositório 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 and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials |
title |
Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials |
spellingShingle |
Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials Oliveira, Elisabete J. Bis-indolylmethanes Solvatochromism Synthesis Heterocycles Thiophene Pyrrole UV-visible spectroscopy Arylthiophene pi-bridges Ciências Naturais::Ciências Químicas Science & Technology |
title_short |
Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials |
title_full |
Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials |
title_fullStr |
Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials |
title_full_unstemmed |
Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials |
title_sort |
Synthesis and solvatochromism studies of novel bis(indolyl)methanes bearing functionalized arylthiophene groups as new colored materials |
author |
Oliveira, Elisabete J. |
author_facet |
Oliveira, Elisabete J. Batista, Rosa Maria Ferreira Costa, Susana P. G. Raposo, M. Manuela M. Lodeiro, Carlos |
author_role |
author |
author2 |
Batista, Rosa Maria Ferreira Costa, Susana P. G. Raposo, M. Manuela M. Lodeiro, Carlos |
author2_role |
author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Oliveira, Elisabete J. Batista, Rosa Maria Ferreira Costa, Susana P. G. Raposo, M. Manuela M. Lodeiro, Carlos |
dc.subject.por.fl_str_mv |
Bis-indolylmethanes Solvatochromism Synthesis Heterocycles Thiophene Pyrrole UV-visible spectroscopy Arylthiophene pi-bridges Ciências Naturais::Ciências Químicas Science & Technology |
topic |
Bis-indolylmethanes Solvatochromism Synthesis Heterocycles Thiophene Pyrrole UV-visible spectroscopy Arylthiophene pi-bridges Ciências Naturais::Ciências Químicas Science & Technology |
description |
The demand for dyes with solvatochromic properties has increased in the last few years, mainly due to their wide range of applications in the analytical and industrial fields, such as in the textile industry. The phenomenon of solvatochromism is associated with the differential solvation of the ground and excited states of the solvatochromic compounds, leading to an important tool for the study of the nature of solute–solvent interactions. In this paper we report the synthesis of new bis(indolyl)methane derivatives bearing arylthiophene spacers (2a–d) functionalized with electron-donating and electron- withdrawing groups, and the photophysical studies in different solvents, such as ethanol, acetonitrile, dichloromethane, trichloromethane, dimethylsulfoxide, diethylether and 1,4-dioxane. Aiming to explore their solvatochromic behavior in the ground and excited states, all solvents employed have different hydrogen-bond donor abilities. The largest colour modifications were visualized for compound 2b, the solution colours of which are orange in DMSO, blue in trichloromethane, green in dichloromethane and purple in 1,4-dioxane. A negative solvatochromism was observed in 2b and positive one in 2a, 2c and 2d. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014 2014-01-01T00:00:00Z |
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/1822/32116 |
url |
http://hdl.handle.net/1822/32116 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
1474-905X 10.1039/C3PP50352F |
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 |
Royal Society of Chemistry |
publisher.none.fl_str_mv |
Royal Society of Chemistry |
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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1799132312868225024 |