Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer Blends

A new rod-shaped benzothiadiazole fluorophore, namely, 4,7-di-(4-nonylphenyl)benzo[c][1,2,5]thiadiazole, which strongly emits fluorescence both in solution and in solid state has been synthesized, and its photophysical properties were rationalized with the help of density functional theory calculati...

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Autores: Echeverri, Marcelo, Ruiz, Constanza, Gámez-Valenzuela, S., Alonso Navarro, Matías, Gutiérrez-Puebla, Enrique, José L. Serrano, Ruiz Delgado, M. Carmen, Gómez-Lor, Berta
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/413926
Acceso en línea:http://hdl.handle.net/10261/413926
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85080137159&doi=10.1021%2Facsami.9b21209&partnerID=40&md5=ebc550da7e36d9d00414f7e20a77ff24
Access Level:acceso abierto
Palabra clave:benzothiadiazole
fluorescence
mechanochromism
phase transformation
polymorphism
thermochromism
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spelling Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer BlendsEcheverri, MarceloRuiz, ConstanzaGámez-Valenzuela, S.Alonso Navarro, MatíasGutiérrez-Puebla, EnriqueJosé L. SerranoRuiz Delgado, M. CarmenGómez-Lor, Bertabenzothiadiazolefluorescencemechanochromismphase transformationpolymorphismthermochromismA new rod-shaped benzothiadiazole fluorophore, namely, 4,7-di-(4-nonylphenyl)benzo[c][1,2,5]thiadiazole, which strongly emits fluorescence both in solution and in solid state has been synthesized, and its photophysical properties were rationalized with the help of density functional theory calculations. This molecule crystallizes in two distinct light-emitting crystalline phases, which can be interconverted in response to pressure, temperature, and solvent vapors. Powder X-ray diffraction indicates that in both polymorph, molecules adopt a lamellar packing, the different interlayer spacing being the main difference between the two structures. Single-crystal analysis of one of the polymorphs allows us to identify weak interaction planes, which presumably facilitates the polymorphic transformation through mechanically or thermally induced sliding processes. The polymorphic transformation and the origin of the switchable fluorescence have been rationalized through a spectroscopic and theoretical study. This study suggests that the different colors observed are due to different intermolecular aromatic interactions owing to the displacement of the molecules with respect to the layer normal. Interestingly, blending this molecule with a biodegradable polymer such as poly(vinyl alcohol) gives rise to a thermally activated reversible switchable fluorescent system, which entitles this material as an attractive candidate for technological applications, such as thermal sensors, security inks, or rewritable paper. © © 2020 American Chemical Society.The work at the ICMM in Madrid was financially supported by the MINECO of Spain (CTQ2016-78557-R). The work at the University of Málaga was funded by the MINECO (CTQ2016-78557-R) and Junta de Andalucía (P09-FQM-4708, UMA18-FEDERJA-080) projects. The authors thankfully acknowledge the computer resources, technical expertise, and assistance provided by the SCBI (Supercomputing and Bioinformatics) centre of the University of Malaga. S. G. V. thanks the MINECO for a FPU predoctoral fellowship (FPU 17/04908).Peer reviewedACS PublicationsMinisterio de Economía y Competitividad (España)Agencia Estatal de Investigación (España)Junta de AndalucíaConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202620262020info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/413926https://www.scopus.com/inward/record.uri?eid=2-s2.0-85080137159&doi=10.1021%2Facsami.9b21209&partnerID=40&md5=ebc550da7e36d9d00414f7e20a77ff24reponame: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/AEI//CTQ2016-78557-RP09-FQM-4708, UMA18-FEDERJA-080info:eu-repo/grantAgreement/AEI//ACS Applied Materials and Interfaceshttps://doi.org/10.1021/acsami.9b21209Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/4139262026-05-22T06:33:51Z
dc.title.none.fl_str_mv Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer Blends
title Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer Blends
spellingShingle Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer Blends
Echeverri, Marcelo
benzothiadiazole
fluorescence
mechanochromism
phase transformation
polymorphism
thermochromism
title_short Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer Blends
title_full Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer Blends
title_fullStr Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer Blends
title_full_unstemmed Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer Blends
title_sort Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer Blends
dc.creator.none.fl_str_mv Echeverri, Marcelo
Ruiz, Constanza
Gámez-Valenzuela, S.
Alonso Navarro, Matías
Gutiérrez-Puebla, Enrique
José L. Serrano
Ruiz Delgado, M. Carmen
Gómez-Lor, Berta
author Echeverri, Marcelo
author_facet Echeverri, Marcelo
Ruiz, Constanza
Gámez-Valenzuela, S.
Alonso Navarro, Matías
Gutiérrez-Puebla, Enrique
José L. Serrano
Ruiz Delgado, M. Carmen
Gómez-Lor, Berta
author_role author
author2 Ruiz, Constanza
Gámez-Valenzuela, S.
Alonso Navarro, Matías
Gutiérrez-Puebla, Enrique
José L. Serrano
Ruiz Delgado, M. Carmen
Gómez-Lor, Berta
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Agencia Estatal de Investigación (España)
Junta de Andalucía
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv benzothiadiazole
fluorescence
mechanochromism
phase transformation
polymorphism
thermochromism
topic benzothiadiazole
fluorescence
mechanochromism
phase transformation
polymorphism
thermochromism
description A new rod-shaped benzothiadiazole fluorophore, namely, 4,7-di-(4-nonylphenyl)benzo[c][1,2,5]thiadiazole, which strongly emits fluorescence both in solution and in solid state has been synthesized, and its photophysical properties were rationalized with the help of density functional theory calculations. This molecule crystallizes in two distinct light-emitting crystalline phases, which can be interconverted in response to pressure, temperature, and solvent vapors. Powder X-ray diffraction indicates that in both polymorph, molecules adopt a lamellar packing, the different interlayer spacing being the main difference between the two structures. Single-crystal analysis of one of the polymorphs allows us to identify weak interaction planes, which presumably facilitates the polymorphic transformation through mechanically or thermally induced sliding processes. The polymorphic transformation and the origin of the switchable fluorescence have been rationalized through a spectroscopic and theoretical study. This study suggests that the different colors observed are due to different intermolecular aromatic interactions owing to the displacement of the molecules with respect to the layer normal. Interestingly, blending this molecule with a biodegradable polymer such as poly(vinyl alcohol) gives rise to a thermally activated reversible switchable fluorescent system, which entitles this material as an attractive candidate for technological applications, such as thermal sensors, security inks, or rewritable paper. © © 2020 American Chemical Society.
publishDate 2020
dc.date.none.fl_str_mv 2020
2026
2026
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/10261/413926
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85080137159&doi=10.1021%2Facsami.9b21209&partnerID=40&md5=ebc550da7e36d9d00414f7e20a77ff24
url http://hdl.handle.net/10261/413926
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85080137159&doi=10.1021%2Facsami.9b21209&partnerID=40&md5=ebc550da7e36d9d00414f7e20a77ff24
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/AEI//CTQ2016-78557-R
P09-FQM-4708, UMA18-FEDERJA-080
info:eu-repo/grantAgreement/AEI//
ACS Applied Materials and Interfaces
https://doi.org/10.1021/acsami.9b21209
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv ACS Publications
publisher.none.fl_str_mv ACS Publications
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
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