Photochromic heteroarylethenes with fast thermal isomerization kinetics
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Outros Autores: | , , |
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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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 |
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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 |
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