Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties

Autores
Gillanders, Florencia; Giordano, Luciana; Diaz, Sebastian Andres; Jovin, Tomás; Jares, Elizabeth Andrea
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Photoswitchable fluorescent diheteroarylethenes are promising candidates for applications in super-resolution molecular localization fluorescence microscopy thanks to their high quantum yields and fatigue-resistant photoswitching characteristics. We have studied the effect of varying substituents on the photophysical properties of six sulfone derivatives of diheteroarylethenes, which display fluorescence in one (closed form) of two thermally stable photochromic states. Electron-donating substituents displace the absorption and emission spectra towards the red without substantially affecting the fluorescence quantum yields. Furthermore, ethoxybromo, a very electron-donating substituent, stabilizes the excited state of the closed isomer to the extent of almost entirely inhibiting its cycloreversion. Multi-parameter Hammett correlations indicate a relationship between the emission maxima and electron-donating character, providing a useful tool in the design of future photochromic molecules. Most of the synthesized compounds exhibit small bathochromic shifts and shorter fluorescence lifetimes with an increase in solvent polarity. However, the ethoxybromo-substituted fluorescent photochrome is unique in its strong solvatochromic behaviour, constituting a photoactivatable (photochromic), fluorescent and highly solvatochromic small organic compound. The Catalán formalism identified solvent dipolarity as the principal basis of the solvatochromism, reflecting the highly polarized nature of this molecule.
Fil: Gillanders, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Centro de Investigaciones en Bionanociencias "Elizabeth Jares Erijman"; Argentina. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Giordano, Luciana. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Centro de Investigaciones en Bionanociencias "Elizabeth Jares Erijman"; Argentina. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; Alemania
Fil: Diaz, Sebastian Andres. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; Alemania
Fil: Jovin, Tomás. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; Alemania
Fil: Jares, Elizabeth Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Materia
Photochromism
Fluorescence
Solvatochromism
Diheteroarylethene
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/4097
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/4097
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic propertiesGillanders, FlorenciaGiordano, LucianaDiaz, Sebastian AndresJovin, TomásJares, Elizabeth AndreaPhotochromismFluorescenceSolvatochromismDiheteroarylethenehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Photoswitchable fluorescent diheteroarylethenes are promising candidates for applications in super-resolution molecular localization fluorescence microscopy thanks to their high quantum yields and fatigue-resistant photoswitching characteristics. We have studied the effect of varying substituents on the photophysical properties of six sulfone derivatives of diheteroarylethenes, which display fluorescence in one (closed form) of two thermally stable photochromic states. Electron-donating substituents displace the absorption and emission spectra towards the red without substantially affecting the fluorescence quantum yields. Furthermore, ethoxybromo, a very electron-donating substituent, stabilizes the excited state of the closed isomer to the extent of almost entirely inhibiting its cycloreversion. Multi-parameter Hammett correlations indicate a relationship between the emission maxima and electron-donating character, providing a useful tool in the design of future photochromic molecules. Most of the synthesized compounds exhibit small bathochromic shifts and shorter fluorescence lifetimes with an increase in solvent polarity. However, the ethoxybromo-substituted fluorescent photochrome is unique in its strong solvatochromic behaviour, constituting a photoactivatable (photochromic), fluorescent and highly solvatochromic small organic compound. The Catalán formalism identified solvent dipolarity as the principal basis of the solvatochromism, reflecting the highly polarized nature of this molecule.Fil: Gillanders, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Centro de Investigaciones en Bionanociencias "Elizabeth Jares Erijman"; Argentina. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Giordano, Luciana. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Centro de Investigaciones en Bionanociencias "Elizabeth Jares Erijman"; Argentina. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; AlemaniaFil: Diaz, Sebastian Andres. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; AlemaniaFil: Jovin, Tomás. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; AlemaniaFil: Jares, Elizabeth Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; ArgentinaRoyal Society of Chemistry2014-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/4097Gillanders, Florencia; Giordano, Luciana; Diaz, Sebastian Andres; Jovin, Tomás; Jares, Elizabeth Andrea; Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 13; 3; 1-2014; 603-6121474-905Xenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/content/articlelanding/2014/pp/c3pp50374g#!divAbstractinfo:eu-repo/semantics/altIdentifier/doi/10.1039/C3PP50374Ginfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:24:53Zoai:ri.conicet.gov.ar:11336/4097instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:24:53.43CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties
title Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties
spellingShingle Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties
Gillanders, Florencia
Photochromism
Fluorescence
Solvatochromism
Diheteroarylethene
title_short Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties
title_full Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties
title_fullStr Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties
title_full_unstemmed Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties
title_sort Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties
dc.creator.none.fl_str_mv Gillanders, Florencia
Giordano, Luciana
Diaz, Sebastian Andres
Jovin, Tomás
Jares, Elizabeth Andrea
author Gillanders, Florencia
author_facet Gillanders, Florencia
Giordano, Luciana
Diaz, Sebastian Andres
Jovin, Tomás
Jares, Elizabeth Andrea
author_role author
author2 Giordano, Luciana
Diaz, Sebastian Andres
Jovin, Tomás
Jares, Elizabeth Andrea
author2_role author
author
author
author
dc.subject.none.fl_str_mv Photochromism
Fluorescence
Solvatochromism
Diheteroarylethene
topic Photochromism
Fluorescence
Solvatochromism
Diheteroarylethene
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Photoswitchable fluorescent diheteroarylethenes are promising candidates for applications in super-resolution molecular localization fluorescence microscopy thanks to their high quantum yields and fatigue-resistant photoswitching characteristics. We have studied the effect of varying substituents on the photophysical properties of six sulfone derivatives of diheteroarylethenes, which display fluorescence in one (closed form) of two thermally stable photochromic states. Electron-donating substituents displace the absorption and emission spectra towards the red without substantially affecting the fluorescence quantum yields. Furthermore, ethoxybromo, a very electron-donating substituent, stabilizes the excited state of the closed isomer to the extent of almost entirely inhibiting its cycloreversion. Multi-parameter Hammett correlations indicate a relationship between the emission maxima and electron-donating character, providing a useful tool in the design of future photochromic molecules. Most of the synthesized compounds exhibit small bathochromic shifts and shorter fluorescence lifetimes with an increase in solvent polarity. However, the ethoxybromo-substituted fluorescent photochrome is unique in its strong solvatochromic behaviour, constituting a photoactivatable (photochromic), fluorescent and highly solvatochromic small organic compound. The Catalán formalism identified solvent dipolarity as the principal basis of the solvatochromism, reflecting the highly polarized nature of this molecule.
Fil: Gillanders, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Centro de Investigaciones en Bionanociencias "Elizabeth Jares Erijman"; Argentina. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Giordano, Luciana. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Centro de Investigaciones en Bionanociencias "Elizabeth Jares Erijman"; Argentina. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; Alemania
Fil: Diaz, Sebastian Andres. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; Alemania
Fil: Jovin, Tomás. Max Planck Institute for Biophysical Chemistry. Laboratory of Cellular Dynamics; Alemania
Fil: Jares, Elizabeth Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
description Photoswitchable fluorescent diheteroarylethenes are promising candidates for applications in super-resolution molecular localization fluorescence microscopy thanks to their high quantum yields and fatigue-resistant photoswitching characteristics. We have studied the effect of varying substituents on the photophysical properties of six sulfone derivatives of diheteroarylethenes, which display fluorescence in one (closed form) of two thermally stable photochromic states. Electron-donating substituents displace the absorption and emission spectra towards the red without substantially affecting the fluorescence quantum yields. Furthermore, ethoxybromo, a very electron-donating substituent, stabilizes the excited state of the closed isomer to the extent of almost entirely inhibiting its cycloreversion. Multi-parameter Hammett correlations indicate a relationship between the emission maxima and electron-donating character, providing a useful tool in the design of future photochromic molecules. Most of the synthesized compounds exhibit small bathochromic shifts and shorter fluorescence lifetimes with an increase in solvent polarity. However, the ethoxybromo-substituted fluorescent photochrome is unique in its strong solvatochromic behaviour, constituting a photoactivatable (photochromic), fluorescent and highly solvatochromic small organic compound. The Catalán formalism identified solvent dipolarity as the principal basis of the solvatochromism, reflecting the highly polarized nature of this molecule.
publishDate 2014
dc.date.none.fl_str_mv 2014-01
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/4097
Gillanders, Florencia; Giordano, Luciana; Diaz, Sebastian Andres; Jovin, Tomás; Jares, Elizabeth Andrea; Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 13; 3; 1-2014; 603-612
1474-905X
url http://hdl.handle.net/11336/4097
identifier_str_mv Gillanders, Florencia; Giordano, Luciana; Diaz, Sebastian Andres; Jovin, Tomás; Jares, Elizabeth Andrea; Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 13; 3; 1-2014; 603-612
1474-905X
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/content/articlelanding/2014/pp/c3pp50374g#!divAbstract
info:eu-repo/semantics/altIdentifier/doi/10.1039/C3PP50374G
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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