Highly solvatochromic 7-aryl-3-hydroxychromones

Autores
Giordano, Luciana; Shvadchak, Volodymyr V.; Fauerbach, Jonathan Arturo; Jares, Elizabeth Andrea; Jovin, Thomas M.
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Introduction of the dialkylaminophenyl group in position 7 of 3-hydroxychromone changes the orientation of the excited-state dipole moment and leads to superior solvatochromic properties (>170 nm emission shift in aprotic media). The excited-state intramolecular proton-transfer (ESIPT) reaction of 7-aryl-3-hydroxychromones is almost completely inhibited in most solvents. Methylation of the 3-OH abolishes ESIPT completely and also leads to improved photostability. The probes exhibit a ∼100-fold increase in fluorescence intensity and large Stokes shifts upon binding to membranes, reflecting differences in membrane phase and charge by a >40 nm spread in the emission band position.
Fil: Giordano, Luciana. Max Planck Institute For Biophysical Chemistry; Alemania
Fil: Shvadchak, Volodymyr V.. Max Planck Institute For Biophysical Chemistry; Alemania
Fil: Fauerbach, Jonathan Arturo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Jares, Elizabeth Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Jovin, Thomas M.. Max Planck Institute For Biophysical Chemistry; Alemania
Materia
Environment-Sensitive
Prodan
Fluorescence
Probe
Esipt
Liposome
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:11336/68171
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Highly solvatochromic 7-aryl-3-hydroxychromonesGiordano, LucianaShvadchak, Volodymyr V.Fauerbach, Jonathan ArturoJares, Elizabeth AndreaJovin, Thomas M.Environment-SensitiveProdanFluorescenceProbeEsiptLiposomehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Introduction of the dialkylaminophenyl group in position 7 of 3-hydroxychromone changes the orientation of the excited-state dipole moment and leads to superior solvatochromic properties (>170 nm emission shift in aprotic media). The excited-state intramolecular proton-transfer (ESIPT) reaction of 7-aryl-3-hydroxychromones is almost completely inhibited in most solvents. Methylation of the 3-OH abolishes ESIPT completely and also leads to improved photostability. The probes exhibit a ∼100-fold increase in fluorescence intensity and large Stokes shifts upon binding to membranes, reflecting differences in membrane phase and charge by a >40 nm spread in the emission band position.Fil: Giordano, Luciana. Max Planck Institute For Biophysical Chemistry; AlemaniaFil: Shvadchak, Volodymyr V.. Max Planck Institute For Biophysical Chemistry; AlemaniaFil: Fauerbach, Jonathan Arturo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Jares, Elizabeth Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Jovin, Thomas M.. Max Planck Institute For Biophysical Chemistry; AlemaniaAmerican Chemical Society2012-04info: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/11336/68171Giordano, Luciana; Shvadchak, Volodymyr V.; Fauerbach, Jonathan Arturo; Jares, Elizabeth Andrea; Jovin, Thomas M.; Highly solvatochromic 7-aryl-3-hydroxychromones; American Chemical Society; Journal of Physical Chemistry Letters; 3; 8; 4-2012; 1011-10161948-7185CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/pdf/10.1021/jz3002019info:eu-repo/semantics/altIdentifier/doi/10.1021/jz3002019info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:21:40Zoai:ri.conicet.gov.ar:11336/68171instacron: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:34982025-09-10 13:21:40.745CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Highly solvatochromic 7-aryl-3-hydroxychromones
title Highly solvatochromic 7-aryl-3-hydroxychromones
spellingShingle Highly solvatochromic 7-aryl-3-hydroxychromones
Giordano, Luciana
Environment-Sensitive
Prodan
Fluorescence
Probe
Esipt
Liposome
title_short Highly solvatochromic 7-aryl-3-hydroxychromones
title_full Highly solvatochromic 7-aryl-3-hydroxychromones
title_fullStr Highly solvatochromic 7-aryl-3-hydroxychromones
title_full_unstemmed Highly solvatochromic 7-aryl-3-hydroxychromones
title_sort Highly solvatochromic 7-aryl-3-hydroxychromones
dc.creator.none.fl_str_mv Giordano, Luciana
Shvadchak, Volodymyr V.
Fauerbach, Jonathan Arturo
Jares, Elizabeth Andrea
Jovin, Thomas M.
author Giordano, Luciana
author_facet Giordano, Luciana
Shvadchak, Volodymyr V.
Fauerbach, Jonathan Arturo
Jares, Elizabeth Andrea
Jovin, Thomas M.
author_role author
author2 Shvadchak, Volodymyr V.
Fauerbach, Jonathan Arturo
Jares, Elizabeth Andrea
Jovin, Thomas M.
author2_role author
author
author
author
dc.subject.none.fl_str_mv Environment-Sensitive
Prodan
Fluorescence
Probe
Esipt
Liposome
topic Environment-Sensitive
Prodan
Fluorescence
Probe
Esipt
Liposome
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Introduction of the dialkylaminophenyl group in position 7 of 3-hydroxychromone changes the orientation of the excited-state dipole moment and leads to superior solvatochromic properties (>170 nm emission shift in aprotic media). The excited-state intramolecular proton-transfer (ESIPT) reaction of 7-aryl-3-hydroxychromones is almost completely inhibited in most solvents. Methylation of the 3-OH abolishes ESIPT completely and also leads to improved photostability. The probes exhibit a ∼100-fold increase in fluorescence intensity and large Stokes shifts upon binding to membranes, reflecting differences in membrane phase and charge by a >40 nm spread in the emission band position.
Fil: Giordano, Luciana. Max Planck Institute For Biophysical Chemistry; Alemania
Fil: Shvadchak, Volodymyr V.. Max Planck Institute For Biophysical Chemistry; Alemania
Fil: Fauerbach, Jonathan Arturo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Jares, Elizabeth Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Jovin, Thomas M.. Max Planck Institute For Biophysical Chemistry; Alemania
description Introduction of the dialkylaminophenyl group in position 7 of 3-hydroxychromone changes the orientation of the excited-state dipole moment and leads to superior solvatochromic properties (>170 nm emission shift in aprotic media). The excited-state intramolecular proton-transfer (ESIPT) reaction of 7-aryl-3-hydroxychromones is almost completely inhibited in most solvents. Methylation of the 3-OH abolishes ESIPT completely and also leads to improved photostability. The probes exhibit a ∼100-fold increase in fluorescence intensity and large Stokes shifts upon binding to membranes, reflecting differences in membrane phase and charge by a >40 nm spread in the emission band position.
publishDate 2012
dc.date.none.fl_str_mv 2012-04
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/11336/68171
Giordano, Luciana; Shvadchak, Volodymyr V.; Fauerbach, Jonathan Arturo; Jares, Elizabeth Andrea; Jovin, Thomas M.; Highly solvatochromic 7-aryl-3-hydroxychromones; American Chemical Society; Journal of Physical Chemistry Letters; 3; 8; 4-2012; 1011-1016
1948-7185
CONICET Digital
CONICET
url http://hdl.handle.net/11336/68171
identifier_str_mv Giordano, Luciana; Shvadchak, Volodymyr V.; Fauerbach, Jonathan Arturo; Jares, Elizabeth Andrea; Jovin, Thomas M.; Highly solvatochromic 7-aryl-3-hydroxychromones; American Chemical Society; Journal of Physical Chemistry Letters; 3; 8; 4-2012; 1011-1016
1948-7185
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/pdf/10.1021/jz3002019
info:eu-repo/semantics/altIdentifier/doi/10.1021/jz3002019
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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
_version_ 1842981190898810880
score 12.48226

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