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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/71874
Ver los metadatos del registro completo
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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 Técnicas2025-09-03T09:53:30Zoai: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:34982025-09-03 09:53:30.484CONICET 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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1842269229404913664 |
score |
13.13397 |