Synthesis of photochromic compounds for aqueous solutions and focusable light

Autores
Polyakova, Svetlana M.; Belov, Vladimir N.; Bossi, Mariano Luis; Hell, Stefan W.
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Photochromic compounds with improved performance in pure water have been prepared and characterized. They possess an asymmetrical and extended conjugation system with a 1,2-bis(3-thienyl)perfluorocyclopentene core, additional thiophene rings connected with sulfonic acid residues, as well as terminal pyrid-4-yl and 4-alkoxyphenyl groups. A multistep synthetic route to a key compound with an amino group required for further derivatization has been developed. The complete photocyclization reaction of the initial "open ring" compound (with absorption maximum at 340 nm in MeOH or water) can be performed with a diode laser in pure water or aqueous buffer solutions (without added or-ganic solvents) under irradiation at 366-375 nm, and the reverse ring-opening reaction of the colored "closed ring" compound (λmax = 628 or 624 nm in MeOH or water) takes place under irradiation with visible green or red light (>500 nm). Building block 57, with a secondary amino group, can further be used in the synthesis of practically important, reversibly switchable, fluorescent compounds in which the fluorescent dye (donor) is attached to a photochromic unit (acceptor), and the resonant energy transfer from a donor to the colored form of an acceptor provides a reversible quenching of the fluorescence signal in aqueous solutions. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fil: Polyakova, Svetlana M.. Max Planck Institute for Biophysical Chemistry; Alemania. Institute of Organic Chemistry and Biochemistry; Alemania
Fil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Bossi, Mariano Luis. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; Alemania
Materia
Cyclization
Heterocycles
Molecular Devices
Photochromism
Solvent Effects
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:11336/71874
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/71874
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of photochromic compounds for aqueous solutions and focusable lightPolyakova, Svetlana M.Belov, Vladimir N.Bossi, Mariano LuisHell, Stefan W.CyclizationHeterocyclesMolecular DevicesPhotochromismSolvent Effectshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Photochromic compounds with improved performance in pure water have been prepared and characterized. They possess an asymmetrical and extended conjugation system with a 1,2-bis(3-thienyl)perfluorocyclopentene core, additional thiophene rings connected with sulfonic acid residues, as well as terminal pyrid-4-yl and 4-alkoxyphenyl groups. A multistep synthetic route to a key compound with an amino group required for further derivatization has been developed. The complete photocyclization reaction of the initial "open ring" compound (with absorption maximum at 340 nm in MeOH or water) can be performed with a diode laser in pure water or aqueous buffer solutions (without added or-ganic solvents) under irradiation at 366-375 nm, and the reverse ring-opening reaction of the colored "closed ring" compound (λmax = 628 or 624 nm in MeOH or water) takes place under irradiation with visible green or red light (>500 nm). Building block 57, with a secondary amino group, can further be used in the synthesis of practically important, reversibly switchable, fluorescent compounds in which the fluorescent dye (donor) is attached to a photochromic unit (acceptor), and the resonant energy transfer from a donor to the colored form of an acceptor provides a reversible quenching of the fluorescence signal in aqueous solutions. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.Fil: Polyakova, Svetlana M.. Max Planck Institute for Biophysical Chemistry; Alemania. Institute of Organic Chemistry and Biochemistry; AlemaniaFil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Bossi, Mariano Luis. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Max Planck Institute for Biophysical Chemistry; AlemaniaFil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; AlemaniaWiley VCH Verlag2011-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/71874Polyakova, Svetlana M.; Belov, Vladimir N.; Bossi, Mariano Luis; Hell, Stefan W.; Synthesis of photochromic compounds for aqueous solutions and focusable light; Wiley VCH Verlag; European Journal of Organic Chemistry; 18; 6-2011; 3301-33121434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201100166info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201100166info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:52:46Zoai:ri.conicet.gov.ar:11336/71874instacron: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 09:52:46.789CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of photochromic compounds for aqueous solutions and focusable light
title Synthesis of photochromic compounds for aqueous solutions and focusable light
spellingShingle Synthesis of photochromic compounds for aqueous solutions and focusable light
Polyakova, Svetlana M.
Cyclization
Heterocycles
Molecular Devices
Photochromism
Solvent Effects
title_short Synthesis of photochromic compounds for aqueous solutions and focusable light
title_full Synthesis of photochromic compounds for aqueous solutions and focusable light
title_fullStr Synthesis of photochromic compounds for aqueous solutions and focusable light
title_full_unstemmed Synthesis of photochromic compounds for aqueous solutions and focusable light
title_sort Synthesis of photochromic compounds for aqueous solutions and focusable light
dc.creator.none.fl_str_mv Polyakova, Svetlana M.
Belov, Vladimir N.
Bossi, Mariano Luis
Hell, Stefan W.
author Polyakova, Svetlana M.
author_facet Polyakova, Svetlana M.
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 Cyclization
Heterocycles
Molecular Devices
Photochromism
Solvent Effects
topic Cyclization
Heterocycles
Molecular Devices
Photochromism
Solvent Effects
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Photochromic compounds with improved performance in pure water have been prepared and characterized. They possess an asymmetrical and extended conjugation system with a 1,2-bis(3-thienyl)perfluorocyclopentene core, additional thiophene rings connected with sulfonic acid residues, as well as terminal pyrid-4-yl and 4-alkoxyphenyl groups. A multistep synthetic route to a key compound with an amino group required for further derivatization has been developed. The complete photocyclization reaction of the initial "open ring" compound (with absorption maximum at 340 nm in MeOH or water) can be performed with a diode laser in pure water or aqueous buffer solutions (without added or-ganic solvents) under irradiation at 366-375 nm, and the reverse ring-opening reaction of the colored "closed ring" compound (λmax = 628 or 624 nm in MeOH or water) takes place under irradiation with visible green or red light (>500 nm). Building block 57, with a secondary amino group, can further be used in the synthesis of practically important, reversibly switchable, fluorescent compounds in which the fluorescent dye (donor) is attached to a photochromic unit (acceptor), and the resonant energy transfer from a donor to the colored form of an acceptor provides a reversible quenching of the fluorescence signal in aqueous solutions. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fil: Polyakova, Svetlana M.. Max Planck Institute for Biophysical Chemistry; Alemania. Institute of Organic Chemistry and Biochemistry; Alemania
Fil: Belov, Vladimir N.. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Bossi, Mariano Luis. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Max Planck Institute for Biophysical Chemistry; Alemania
Fil: Hell, Stefan W.. Max Planck Institute for Biophysical Chemistry; Alemania
description Photochromic compounds with improved performance in pure water have been prepared and characterized. They possess an asymmetrical and extended conjugation system with a 1,2-bis(3-thienyl)perfluorocyclopentene core, additional thiophene rings connected with sulfonic acid residues, as well as terminal pyrid-4-yl and 4-alkoxyphenyl groups. A multistep synthetic route to a key compound with an amino group required for further derivatization has been developed. The complete photocyclization reaction of the initial "open ring" compound (with absorption maximum at 340 nm in MeOH or water) can be performed with a diode laser in pure water or aqueous buffer solutions (without added or-ganic solvents) under irradiation at 366-375 nm, and the reverse ring-opening reaction of the colored "closed ring" compound (λmax = 628 or 624 nm in MeOH or water) takes place under irradiation with visible green or red light (>500 nm). Building block 57, with a secondary amino group, can further be used in the synthesis of practically important, reversibly switchable, fluorescent compounds in which the fluorescent dye (donor) is attached to a photochromic unit (acceptor), and the resonant energy transfer from a donor to the colored form of an acceptor provides a reversible quenching of the fluorescence signal in aqueous solutions. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
publishDate 2011
dc.date.none.fl_str_mv 2011-06
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/11336/71874
Polyakova, Svetlana M.; Belov, Vladimir N.; Bossi, Mariano Luis; Hell, Stefan W.; Synthesis of photochromic compounds for aqueous solutions and focusable light; Wiley VCH Verlag; European Journal of Organic Chemistry; 18; 6-2011; 3301-3312
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/71874
identifier_str_mv Polyakova, Svetlana M.; Belov, Vladimir N.; Bossi, Mariano Luis; Hell, Stefan W.; Synthesis of photochromic compounds for aqueous solutions and focusable light; Wiley VCH Verlag; European Journal of Organic Chemistry; 18; 6-2011; 3301-3312
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/doi/10.1002/ejoc.201100166
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201100166
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
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