A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes

Detalhes bibliográficos
Autor(a) principal: Rashidnejad, Hamid
Data de Publicação: 2021
Outros Autores: Ramezanitaghartapeh, Mohammad, Pesyan, Nader Noroozi, Mahon, Peter J., Raposo, M. Manuela M., Coelho, Paulo J., Lup, Andrew Ng Kay, Soltani, Alireza
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/74864
Resumo: A series of novel substituted-azo dyes 8-(aryldiazenyl)quinolin-5-ol (5a-i) were synthesized by the coupling reaction of 5-hydroxyquinoline with diazotized aniline derivatives in the presence of NaNO2 in HCl/H2O mixture. The study of the spectroscopic and solvatochromic properties were performed by FT-IR, 1H and 13C-NMR and UV-Visible spectroscopies. The tautomerism of these dyes was studied using the deuteration technique and solvatochromic measurements. Photochromic properties of these 5-hydroxyquinoline azo dyes were also examined via E/Z and Z/E photochemical isomerization reactions and compared with the existing 8-hydroxyquinoline analogous. The novel substituted-azo dyes exhibited higher Z/E thermal isomerization rates and have larger absorbance wavelength range than their 8-hydroxyquinoline analogous, making them potential molecular switches.
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spelling A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes5-hydroxyquinoline8-hydroxyquinolineHeterocyclic azo dyesPhotochromismSolvatochromismTautomerismScience & TechnologyA series of novel substituted-azo dyes 8-(aryldiazenyl)quinolin-5-ol (5a-i) were synthesized by the coupling reaction of 5-hydroxyquinoline with diazotized aniline derivatives in the presence of NaNO2 in HCl/H2O mixture. The study of the spectroscopic and solvatochromic properties were performed by FT-IR, 1H and 13C-NMR and UV-Visible spectroscopies. The tautomerism of these dyes was studied using the deuteration technique and solvatochromic measurements. Photochromic properties of these 5-hydroxyquinoline azo dyes were also examined via E/Z and Z/E photochemical isomerization reactions and compared with the existing 8-hydroxyquinoline analogous. The novel substituted-azo dyes exhibited higher Z/E thermal isomerization rates and have larger absorbance wavelength range than their 8-hydroxyquinoline analogous, making them potential molecular switches.FCT - Swinburne University of Technology(UID/QUI/00686/2020)ElsevierUniversidade do MinhoRashidnejad, HamidRamezanitaghartapeh, MohammadPesyan, Nader NorooziMahon, Peter J.Raposo, M. Manuela M.Coelho, Paulo J.Lup, Andrew Ng KaySoltani, Alireza2021-01-052021-01-05T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/74864eng0022-286010.1016/j.molstruc.2020.129323https://doi.org/10.1016/j.molstruc.2020.129323info: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:RCAAP2023-07-21T12:13:05Zoai:repositorium.sdum.uminho.pt:1822/74864Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:05:06.915510Repositório 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 A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes
title A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes
spellingShingle A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes
Rashidnejad, Hamid
5-hydroxyquinoline
8-hydroxyquinoline
Heterocyclic azo dyes
Photochromism
Solvatochromism
Tautomerism
Science & Technology
title_short A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes
title_full A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes
title_fullStr A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes
title_full_unstemmed A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes
title_sort A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes
author Rashidnejad, Hamid
author_facet Rashidnejad, Hamid
Ramezanitaghartapeh, Mohammad
Pesyan, Nader Noroozi
Mahon, Peter J.
Raposo, M. Manuela M.
Coelho, Paulo J.
Lup, Andrew Ng Kay
Soltani, Alireza
author_role author
author2 Ramezanitaghartapeh, Mohammad
Pesyan, Nader Noroozi
Mahon, Peter J.
Raposo, M. Manuela M.
Coelho, Paulo J.
Lup, Andrew Ng Kay
Soltani, Alireza
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Rashidnejad, Hamid
Ramezanitaghartapeh, Mohammad
Pesyan, Nader Noroozi
Mahon, Peter J.
Raposo, M. Manuela M.
Coelho, Paulo J.
Lup, Andrew Ng Kay
Soltani, Alireza
dc.subject.por.fl_str_mv 5-hydroxyquinoline
8-hydroxyquinoline
Heterocyclic azo dyes
Photochromism
Solvatochromism
Tautomerism
Science & Technology
topic 5-hydroxyquinoline
8-hydroxyquinoline
Heterocyclic azo dyes
Photochromism
Solvatochromism
Tautomerism
Science & Technology
description A series of novel substituted-azo dyes 8-(aryldiazenyl)quinolin-5-ol (5a-i) were synthesized by the coupling reaction of 5-hydroxyquinoline with diazotized aniline derivatives in the presence of NaNO2 in HCl/H2O mixture. The study of the spectroscopic and solvatochromic properties were performed by FT-IR, 1H and 13C-NMR and UV-Visible spectroscopies. The tautomerism of these dyes was studied using the deuteration technique and solvatochromic measurements. Photochromic properties of these 5-hydroxyquinoline azo dyes were also examined via E/Z and Z/E photochemical isomerization reactions and compared with the existing 8-hydroxyquinoline analogous. The novel substituted-azo dyes exhibited higher Z/E thermal isomerization rates and have larger absorbance wavelength range than their 8-hydroxyquinoline analogous, making them potential molecular switches.
publishDate 2021
dc.date.none.fl_str_mv 2021-01-05
2021-01-05T00:00:00Z
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/1822/74864
url http://hdl.handle.net/1822/74864
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0022-2860
10.1016/j.molstruc.2020.129323
https://doi.org/10.1016/j.molstruc.2020.129323
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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