Photochromic heteroarylethenes with fast thermal isomerization kinetics

Detalhes bibliográficos
Autor(a) principal: Garcia-Amorós, Jaume
Data de Publicação: 2023
Outros Autores: Castro, M. Cidália R., Raposo, M. Manuela M., Velasco, Dolores
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: https://hdl.handle.net/1822/80935
Resumo: Supplementary data to this article can be found online at https://doi.org/10.1016/j.dyepig.2022.111000
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spelling Photochromic heteroarylethenes with fast thermal isomerization kineticsazo dyessynthesisheterocyclesthiophenepyrroleHeteroarylethenesIsomerizationMolecular switchesPhotochromismCiências Naturais::Ciências QuímicasScience & TechnologyIndústria, inovação e infraestruturasSupplementary data to this article can be found online at https://doi.org/10.1016/j.dyepig.2022.111000Stilbenes (diphenylethenes) are fully examined organic chromophores for very diverse applications. However, these molecules might show poor stability under irradiation because several simultaneous reactions (oxidative photocyclization and dimerization) can take place during the photochemical isomerization of their C=C bond. In this context, heteroarylethenes emerge as powerful counterparts thanks to their improved stability. In addition, the chosen heterocycles and their functionalization allows to fine tune and increase the speed at which the thermal back reaction occurs, broadening the scope of application of the resulting chromophores. Here we report on the thermal Z-to-E isomerization kinetics of a series of rationally designed heteroarylethenes and how the chemical architecture of the chromophore modulates the speed of the process. Specifically, the metastable Z isomers display relaxation times covering a wide time window, from a few hours to hundreds of microseconds. In fact, one of the studied dyes is the fastest heteroarylethene known to date. It should be also noticed that the described heteroarylethenes exhibit great photochemical stability, it being possible to switch them back and forth many times without degradation.This research was funded by the Ministerio de Ciencia, Innovacion y Universidades (Spain)/Agencia Estatal de Investigacion (Spain)/Fondo Europeo de Dearrollo Regional (FEDER, European Union), grant number PGC2018-095477-B-I00. Thanks are also due to Fundação para a Ciência e Tecnologia (FCT) and to FEDER-COMPETE for financial support through the research center CQUM (UID/QUI/0686/2016) and (UID/ QUI/0686/2020). The NMR spectrometers are part of the National NMR Network (PTNMR) and are partially supported by Infrastructure Project Nº 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC). Authors also thank Prof. Santi Nonell for granting access to the nanosecond laser flash photolysis setup.ElsevierUniversidade do MinhoGarcia-Amorós, JaumeCastro, M. Cidália R.Raposo, M. Manuela M.Velasco, Dolores20232023-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfapplication/pdfhttps://hdl.handle.net/1822/80935engGarcia-Amorós, J.; Castro, M. C. R.; Raposo, M. M. M.; Velasco, D. Stable photochromic heteroarylethenes with fast thermal isomerization kinetics. Dyes Pigments. 2023, 210, 111000. https://doi.org/10.1016/j.dyepig.2022.1110000143-720810.1016/j.dyepig.2022.111000111000https://doi.org/10.1016/j.dyepig.2022.111000info: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:RCAAP2023-12-23T01:36:38Zoai:repositorium.sdum.uminho.pt:1822/80935Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:48:17.679591Repositório 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 Photochromic heteroarylethenes with fast thermal isomerization kinetics
title Photochromic heteroarylethenes with fast thermal isomerization kinetics
spellingShingle Photochromic heteroarylethenes with fast thermal isomerization kinetics
Garcia-Amorós, Jaume
azo dyes
synthesis
heterocycles
thiophene
pyrrole
Heteroarylethenes
Isomerization
Molecular switches
Photochromism
Ciências Naturais::Ciências Químicas
Science & Technology
Indústria, inovação e infraestruturas
title_short Photochromic heteroarylethenes with fast thermal isomerization kinetics
title_full Photochromic heteroarylethenes with fast thermal isomerization kinetics
title_fullStr Photochromic heteroarylethenes with fast thermal isomerization kinetics
title_full_unstemmed Photochromic heteroarylethenes with fast thermal isomerization kinetics
title_sort Photochromic heteroarylethenes with fast thermal isomerization kinetics
author Garcia-Amorós, Jaume
author_facet Garcia-Amorós, Jaume
Castro, M. Cidália R.
Raposo, M. Manuela M.
Velasco, Dolores
author_role author
author2 Castro, M. Cidália R.
Raposo, M. Manuela M.
Velasco, Dolores
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Garcia-Amorós, Jaume
Castro, M. Cidália R.
Raposo, M. Manuela M.
Velasco, Dolores
dc.subject.por.fl_str_mv azo dyes
synthesis
heterocycles
thiophene
pyrrole
Heteroarylethenes
Isomerization
Molecular switches
Photochromism
Ciências Naturais::Ciências Químicas
Science & Technology
Indústria, inovação e infraestruturas
topic azo dyes
synthesis
heterocycles
thiophene
pyrrole
Heteroarylethenes
Isomerization
Molecular switches
Photochromism
Ciências Naturais::Ciências Químicas
Science & Technology
Indústria, inovação e infraestruturas
description Supplementary data to this article can be found online at https://doi.org/10.1016/j.dyepig.2022.111000
publishDate 2023
dc.date.none.fl_str_mv 2023
2023-01-01T00:00:00Z
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 https://hdl.handle.net/1822/80935
url https://hdl.handle.net/1822/80935
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Garcia-Amorós, J.; Castro, M. C. R.; Raposo, M. M. M.; Velasco, D. Stable photochromic heteroarylethenes with fast thermal isomerization kinetics. Dyes Pigments. 2023, 210, 111000. https://doi.org/10.1016/j.dyepig.2022.111000
0143-7208
10.1016/j.dyepig.2022.111000
111000
https://doi.org/10.1016/j.dyepig.2022.111000
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: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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