Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene

Autores
Yan, Sergey F.; Belov, Vladimir N.; Bossi, Mariano Luis; Hell, Stefan W.
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
New fluorescent photochromic compounds (1-H and 1-Boc)have been synthesized and characterized in different solvents.The fluorescence emission can be switched “on” and“off” with visible light and UV, respectively, by means of thephotochromic reaction. The emission wavelength and efficiencystrongly depend on the polarity of the solvent. Thecompounds show a positive solvatochromic effect in theemission maxima, and their fluorescence quantum yield decreasesas the solvent’s polarity increases (from cyclohexaneto dioxane). In solvents more polar than dioxane the emissionis too weak and therefore undetectable, and thus 1-H and 1-Boc behave as “normal” photochromic compounds. The photochromic reaction is also sensitive to the environment. A decreaseof more than an order of magnitude was found for thequantum yield of the colouring reaction (ΦOFCF) for 1-H inethanol compared with cyclohexane, and an about threefolddecrease in ΦOFCF was observed for the compound 1-Bocin polar solvents (compared with apolar solvents). For bothcompounds the ring-opening reaction was found not to dependenton the solvent. The novel fluorescent molecularswitches 1-H and 1-Boc are able to probe the polarity of theirmicroenvironment.
Fil: Yan, Sergey F.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Bossi, Mariano Luis. Max Planck Institute for Biophysical Chemistry; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Fil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; Alemania
Materia
Fluorescent probes
photochromism
Solvatochromism
Molecular switches
4-Aminophthalimide
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:11336/103010
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/103010
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic DiaryletheneYan, Sergey F.Belov, Vladimir N.Bossi, Mariano LuisHell, Stefan W.Fluorescent probesphotochromismSolvatochromismMolecular switches4-Aminophthalimidehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1New fluorescent photochromic compounds (1-H and 1-Boc)have been synthesized and characterized in different solvents.The fluorescence emission can be switched “on” and“off” with visible light and UV, respectively, by means of thephotochromic reaction. The emission wavelength and efficiencystrongly depend on the polarity of the solvent. Thecompounds show a positive solvatochromic effect in theemission maxima, and their fluorescence quantum yield decreasesas the solvent’s polarity increases (from cyclohexaneto dioxane). In solvents more polar than dioxane the emissionis too weak and therefore undetectable, and thus 1-H and 1-Boc behave as “normal” photochromic compounds. The photochromic reaction is also sensitive to the environment. A decreaseof more than an order of magnitude was found for thequantum yield of the colouring reaction (ΦOFCF) for 1-H inethanol compared with cyclohexane, and an about threefolddecrease in ΦOFCF was observed for the compound 1-Bocin polar solvents (compared with apolar solvents). For bothcompounds the ring-opening reaction was found not to dependenton the solvent. The novel fluorescent molecularswitches 1-H and 1-Boc are able to probe the polarity of theirmicroenvironment.Fil: Yan, Sergey F.. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Bossi, Mariano Luis. Max Planck Institute for Biophysical Chemistry; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; ArgentinaFil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; AlemaniaWiley VCH Verlag2008-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/103010Yan, Sergey F.; Belov, Vladimir N.; Bossi, Mariano Luis; Hell, Stefan W.; Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene; Wiley VCH Verlag; European Journal of Organic Chemistry; 2008; 15; 5-2008; 2531-25381434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200800125info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.200800125info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:48:18Zoai:ri.conicet.gov.ar:11336/103010instacron: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:34982025-09-03 09:48:18.882CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene
title Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene
spellingShingle Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene
Yan, Sergey F.
Fluorescent probes
photochromism
Solvatochromism
Molecular switches
4-Aminophthalimide
title_short Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene
title_full Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene
title_fullStr Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene
title_full_unstemmed Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene
title_sort Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene
dc.creator.none.fl_str_mv Yan, Sergey F.
Belov, Vladimir N.
Bossi, Mariano Luis
Hell, Stefan W.
author Yan, Sergey F.
author_facet Yan, Sergey F.
Belov, Vladimir N.
Bossi, Mariano Luis
Hell, Stefan W.
author_role author
author2 Belov, Vladimir N.
Bossi, Mariano Luis
Hell, Stefan W.
author2_role author
author
author
dc.subject.none.fl_str_mv Fluorescent probes
photochromism
Solvatochromism
Molecular switches
4-Aminophthalimide
topic Fluorescent probes
photochromism
Solvatochromism
Molecular switches
4-Aminophthalimide
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv New fluorescent photochromic compounds (1-H and 1-Boc)have been synthesized and characterized in different solvents.The fluorescence emission can be switched “on” and“off” with visible light and UV, respectively, by means of thephotochromic reaction. The emission wavelength and efficiencystrongly depend on the polarity of the solvent. Thecompounds show a positive solvatochromic effect in theemission maxima, and their fluorescence quantum yield decreasesas the solvent’s polarity increases (from cyclohexaneto dioxane). In solvents more polar than dioxane the emissionis too weak and therefore undetectable, and thus 1-H and 1-Boc behave as “normal” photochromic compounds. The photochromic reaction is also sensitive to the environment. A decreaseof more than an order of magnitude was found for thequantum yield of the colouring reaction (ΦOFCF) for 1-H inethanol compared with cyclohexane, and an about threefolddecrease in ΦOFCF was observed for the compound 1-Bocin polar solvents (compared with apolar solvents). For bothcompounds the ring-opening reaction was found not to dependenton the solvent. The novel fluorescent molecularswitches 1-H and 1-Boc are able to probe the polarity of theirmicroenvironment.
Fil: Yan, Sergey F.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Bossi, Mariano Luis. Max Planck Institute for Biophysical Chemistry; Alemania. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Fil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; Alemania
description New fluorescent photochromic compounds (1-H and 1-Boc)have been synthesized and characterized in different solvents.The fluorescence emission can be switched “on” and“off” with visible light and UV, respectively, by means of thephotochromic reaction. The emission wavelength and efficiencystrongly depend on the polarity of the solvent. Thecompounds show a positive solvatochromic effect in theemission maxima, and their fluorescence quantum yield decreasesas the solvent’s polarity increases (from cyclohexaneto dioxane). In solvents more polar than dioxane the emissionis too weak and therefore undetectable, and thus 1-H and 1-Boc behave as “normal” photochromic compounds. The photochromic reaction is also sensitive to the environment. A decreaseof more than an order of magnitude was found for thequantum yield of the colouring reaction (ΦOFCF) for 1-H inethanol compared with cyclohexane, and an about threefolddecrease in ΦOFCF was observed for the compound 1-Bocin polar solvents (compared with apolar solvents). For bothcompounds the ring-opening reaction was found not to dependenton the solvent. The novel fluorescent molecularswitches 1-H and 1-Boc are able to probe the polarity of theirmicroenvironment.
publishDate 2008
dc.date.none.fl_str_mv 2008-05
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/11336/103010
Yan, Sergey F.; Belov, Vladimir N.; Bossi, Mariano Luis; Hell, Stefan W.; Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene; Wiley VCH Verlag; European Journal of Organic Chemistry; 2008; 15; 5-2008; 2531-2538
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/103010
identifier_str_mv Yan, Sergey F.; Belov, Vladimir N.; Bossi, Mariano Luis; Hell, Stefan W.; Switchable Fluorescent and Solvatochromic Molecular Probes Based on 4-Amino-N-methylphthalimide and a Photochromic Diarylethene; Wiley VCH Verlag; European Journal of Organic Chemistry; 2008; 15; 5-2008; 2531-2538
1434-193X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200800125
info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.200800125
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
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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_ 1842268917491302400
score 13.13397

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