Adaptable Photochromic Switches with Self-Aggregating Heterocyclic Azo Dyes

It is well-known that the thermal isomerization kinetics of photochromic azo dyes can be modulated by subtle changes in their chemical architecture. However, the availability of an orthogonal input to control the thermal relaxation of azo dyes is essential to enable access to multifunctional and ada...

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Detalles Bibliográficos
Autores: García-Amorós, Jaume, Castro, M. Cidália R., Nonell, Santi, Vílchez, Susana, Esquena, Jordi, Raposo, Manuela M., Velasco, Dolores
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/201222
Acceso en línea:http://hdl.handle.net/10261/201222
Access Level:acceso abierto
Palabra clave:Azobenzene
Isomerization
Azobenzene derivatives
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spelling Adaptable Photochromic Switches with Self-Aggregating Heterocyclic Azo DyesRetrospect and Prospect: 30 years of Formula conferences!García-Amorós, JaumeCastro, M. Cidália R.Nonell, SantiVílchez, SusanaEsquena, JordiRaposo, Manuela M.Velasco, DoloresAzobenzeneIsomerizationAzobenzene derivativesIt is well-known that the thermal isomerization kinetics of photochromic azo dyes can be modulated by subtle changes in their chemical architecture. However, the availability of an orthogonal input to control the thermal relaxation of azo dyes is essential to enable access to multifunctional and adaptive photochromic switches based on these particular organic chromophores. In this work, we have designed and synthesized a new family of green-light-activated heterocyclic azo derivatives that modify their switching capabilities as a function of concentration. In this line, we have investigated their self-assembly and the nature of the supramolecular aggregates formed by means of dynamic light scattering, polarized optical microscopy, and X-ray diffraction. Indeed, imparting control over the self-assembly of these organic dyes allows to fine-tune their thermal relaxation time and produce adaptable photochromic switches. Specifically, swapping the azo dye concentration between values located above and below the corresponding critical aggregation concentration modifies significantly the relaxation time up to 250 times, i.e., from the millisecond to the microsecond timescale. Moreover, the optical density of the system can be switched back and forth hundreds of times, for both diluted and concentrated solutions, without any sign of fatigue. © 2019 American Chemical Society.Financial support for this research was obtained from the Ministerio de Economı́a y Competitividad (Spain, PGC2018-095477-B-I00, CTQ2016-78454-C2-1-R, and CTQ2017-84998-P MINECO/FEDER). Thanks are also due to Fundação para a Ciência e Tecnologia (Portugal) for financial support to the Portuguese NMR network (PTNMR, Bruker Avance III 400-Univ. Minho), FCT, and FEDER (European Fund for Regional Development)-COMPETEQREN-EU for financial support to the research centre CQ/UM [ref UID/QUI/00686/2013 and UID/QUI/0686/2016], and a PhD grant to M.C.R.C. (SFRH/BD/78037/2011).Peer reviewedAmerican Chemical SocietyMinisterio de Economía y Competitividad (España)Vílchez, Susana [0000-0002-4793-3831]Esquena, Jordi [0000-0002-9188-5259]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202020202019info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/201222reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-78454-C2-1-Rinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-095477-B-I00info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-84998-Phttps://doi.org/10.1021/acs.jpcc.9b07527Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2012222026-05-22T06:33:51Z
dc.title.none.fl_str_mv Adaptable Photochromic Switches with Self-Aggregating Heterocyclic Azo Dyes
Retrospect and Prospect: 30 years of Formula conferences!
title Adaptable Photochromic Switches with Self-Aggregating Heterocyclic Azo Dyes
spellingShingle Adaptable Photochromic Switches with Self-Aggregating Heterocyclic Azo Dyes
García-Amorós, Jaume
Azobenzene
Isomerization
Azobenzene derivatives
title_short Adaptable Photochromic Switches with Self-Aggregating Heterocyclic Azo Dyes
title_full Adaptable Photochromic Switches with Self-Aggregating Heterocyclic Azo Dyes
title_fullStr Adaptable Photochromic Switches with Self-Aggregating Heterocyclic Azo Dyes
title_full_unstemmed Adaptable Photochromic Switches with Self-Aggregating Heterocyclic Azo Dyes
title_sort Adaptable Photochromic Switches with Self-Aggregating Heterocyclic Azo Dyes
dc.creator.none.fl_str_mv García-Amorós, Jaume
Castro, M. Cidália R.
Nonell, Santi
Vílchez, Susana
Esquena, Jordi
Raposo, Manuela M.
Velasco, Dolores
author García-Amorós, Jaume
author_facet García-Amorós, Jaume
Castro, M. Cidália R.
Nonell, Santi
Vílchez, Susana
Esquena, Jordi
Raposo, Manuela M.
Velasco, Dolores
author_role author
author2 Castro, M. Cidália R.
Nonell, Santi
Vílchez, Susana
Esquena, Jordi
Raposo, Manuela M.
Velasco, Dolores
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Vílchez, Susana [0000-0002-4793-3831]
Esquena, Jordi [0000-0002-9188-5259]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Azobenzene
Isomerization
Azobenzene derivatives
topic Azobenzene
Isomerization
Azobenzene derivatives
description It is well-known that the thermal isomerization kinetics of photochromic azo dyes can be modulated by subtle changes in their chemical architecture. However, the availability of an orthogonal input to control the thermal relaxation of azo dyes is essential to enable access to multifunctional and adaptive photochromic switches based on these particular organic chromophores. In this work, we have designed and synthesized a new family of green-light-activated heterocyclic azo derivatives that modify their switching capabilities as a function of concentration. In this line, we have investigated their self-assembly and the nature of the supramolecular aggregates formed by means of dynamic light scattering, polarized optical microscopy, and X-ray diffraction. Indeed, imparting control over the self-assembly of these organic dyes allows to fine-tune their thermal relaxation time and produce adaptable photochromic switches. Specifically, swapping the azo dye concentration between values located above and below the corresponding critical aggregation concentration modifies significantly the relaxation time up to 250 times, i.e., from the millisecond to the microsecond timescale. Moreover, the optical density of the system can be switched back and forth hundreds of times, for both diluted and concentrated solutions, without any sign of fatigue. © 2019 American Chemical Society.
publishDate 2019
dc.date.none.fl_str_mv 2019
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/201222
url http://hdl.handle.net/10261/201222
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-78454-C2-1-R
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-095477-B-I00
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-84998-P
https://doi.org/10.1021/acs.jpcc.9b07527
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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