Synthesis of 5-aryl-5´-formyl-2,2´-bithiophenes as new precursors for nonlinear optical (NLO) materials

Detalhes bibliográficos
Autor(a) principal: Herbivo, Cyril
Data de Publicação: 2009
Outros Autores: Comel, Alain, Kirsch, G., Raposo, M. Manuela M.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
Texto Completo: https://hdl.handle.net/1822/10645
Resumo: A series of formyl-substituted 5-aryl-2,2´-bithiophenes 5 were synthesized using two different methods: Vilsmeier-Haack-Arnold reaction (VHA) or through Suzuki coupling. The synthesis of compounds 5 through the Vilsmeier-Haack-Arnold reaction, starting from inexpensive and easily available precursors such as acetophenones, gave the title compounds in low yields after four reaction steps. On the other hand Suzuki coupling of functionalized aryl boronic acids 7 and the 5-bromo-5´-formyl-2,2´-bithiophene 6 gave compounds 5 in good yields in only one step.
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spelling Synthesis of 5-aryl-5´-formyl-2,2´-bithiophenes as new precursors for nonlinear optical (NLO) materialsSynthesisVilsmeier-Haack-Arnold (VHA) formylationChloroformylationSuzuki couplingAldehydesFormyl-substituted aryl-bithiophenesπ-conjugated systemsUV-visible spectroscopyNonlinear optical (NLO) precursorsUV-vis spectroscopyp-Conjugated systemsVilsmeier-Haack-Arnold (VHA) chloroformylationScience & TechnologyA series of formyl-substituted 5-aryl-2,2´-bithiophenes 5 were synthesized using two different methods: Vilsmeier-Haack-Arnold reaction (VHA) or through Suzuki coupling. The synthesis of compounds 5 through the Vilsmeier-Haack-Arnold reaction, starting from inexpensive and easily available precursors such as acetophenones, gave the title compounds in low yields after four reaction steps. On the other hand Suzuki coupling of functionalized aryl boronic acids 7 and the 5-bromo-5´-formyl-2,2´-bithiophene 6 gave compounds 5 in good yields in only one step.Fundação para a Ciência e a Tecnologia (FCT)ElsevierUniversidade do MinhoHerbivo, CyrilComel, AlainKirsch, G.Raposo, M. Manuela M.2009-01-082009-01-08T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfapplication/pdfhttps://hdl.handle.net/1822/10645eng"Terahedron". ISSN 0040-4039. 65:10 (Jan. 2009) 2079-2086.0040-403910.1016/j.tet.2008.12.078info:eu-repo/semantics/openAccessreponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiainstacron:RCAAP2025-04-12T05:04:11Zoai:repositorium.sdum.uminho.pt:1822/10645Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireinfo@rcaap.ptopendoar:https://opendoar.ac.uk/repository/71602025-05-28T16:00:12.573856Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiafalse
dc.title.none.fl_str_mv Synthesis of 5-aryl-5´-formyl-2,2´-bithiophenes as new precursors for nonlinear optical (NLO) materials
title Synthesis of 5-aryl-5´-formyl-2,2´-bithiophenes as new precursors for nonlinear optical (NLO) materials
spellingShingle Synthesis of 5-aryl-5´-formyl-2,2´-bithiophenes as new precursors for nonlinear optical (NLO) materials
Herbivo, Cyril
Synthesis
Vilsmeier-Haack-Arnold (VHA) formylation
Chloroformylation
Suzuki coupling
Aldehydes
Formyl-substituted aryl-bithiophenes
π-conjugated systems
UV-visible spectroscopy
Nonlinear optical (NLO) precursors
UV-vis spectroscopy
p-Conjugated systems
Vilsmeier-Haack-Arnold (VHA) chloroformylation
Science & Technology
title_short Synthesis of 5-aryl-5´-formyl-2,2´-bithiophenes as new precursors for nonlinear optical (NLO) materials
title_full Synthesis of 5-aryl-5´-formyl-2,2´-bithiophenes as new precursors for nonlinear optical (NLO) materials
title_fullStr Synthesis of 5-aryl-5´-formyl-2,2´-bithiophenes as new precursors for nonlinear optical (NLO) materials
title_full_unstemmed Synthesis of 5-aryl-5´-formyl-2,2´-bithiophenes as new precursors for nonlinear optical (NLO) materials
title_sort Synthesis of 5-aryl-5´-formyl-2,2´-bithiophenes as new precursors for nonlinear optical (NLO) materials
author Herbivo, Cyril
author_facet Herbivo, Cyril
Comel, Alain
Kirsch, G.
Raposo, M. Manuela M.
author_role author
author2 Comel, Alain
Kirsch, G.
Raposo, M. Manuela M.
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Herbivo, Cyril
Comel, Alain
Kirsch, G.
Raposo, M. Manuela M.
dc.subject.por.fl_str_mv Synthesis
Vilsmeier-Haack-Arnold (VHA) formylation
Chloroformylation
Suzuki coupling
Aldehydes
Formyl-substituted aryl-bithiophenes
π-conjugated systems
UV-visible spectroscopy
Nonlinear optical (NLO) precursors
UV-vis spectroscopy
p-Conjugated systems
Vilsmeier-Haack-Arnold (VHA) chloroformylation
Science & Technology
topic Synthesis
Vilsmeier-Haack-Arnold (VHA) formylation
Chloroformylation
Suzuki coupling
Aldehydes
Formyl-substituted aryl-bithiophenes
π-conjugated systems
UV-visible spectroscopy
Nonlinear optical (NLO) precursors
UV-vis spectroscopy
p-Conjugated systems
Vilsmeier-Haack-Arnold (VHA) chloroformylation
Science & Technology
description A series of formyl-substituted 5-aryl-2,2´-bithiophenes 5 were synthesized using two different methods: Vilsmeier-Haack-Arnold reaction (VHA) or through Suzuki coupling. The synthesis of compounds 5 through the Vilsmeier-Haack-Arnold reaction, starting from inexpensive and easily available precursors such as acetophenones, gave the title compounds in low yields after four reaction steps. On the other hand Suzuki coupling of functionalized aryl boronic acids 7 and the 5-bromo-5´-formyl-2,2´-bithiophene 6 gave compounds 5 in good yields in only one step.
publishDate 2009
dc.date.none.fl_str_mv 2009-01-08
2009-01-08T00:00:00Z
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 https://hdl.handle.net/1822/10645
url https://hdl.handle.net/1822/10645
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv "Terahedron". ISSN 0040-4039. 65:10 (Jan. 2009) 2079-2086.
0040-4039
10.1016/j.tet.2008.12.078
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron:RCAAP
instname_str FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron_str RCAAP
institution RCAAP
reponame_str Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
collection Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
repository.name.fl_str_mv Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
repository.mail.fl_str_mv info@rcaap.pt
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