Highly solvatochromic 7-aryl-3-hydroxychromones

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 o...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Giordano, L., Shvadchak, V.V., Fauerbach, J.A., Jares-Erijman, E.A., Jovin, T.M.
Formato:	JOUR
Materias:	Aprotic media Emission bands Emission shifts Excited-state dipole moment Fluorescence intensities Intramolecular proton-transfer Photo-stability Solvatochromic Solvatochromic properties Stokes shift Alkylation Excited states
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_19487185_v3_n8_p1011_Giordano
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_19487185_v3_n8_p1011_Giordano
record_format	dspace
spelling	todo:paper_19487185_v3_n8_p1011_Giordano2023-10-03T16:37:09Z Highly solvatochromic 7-aryl-3-hydroxychromones Giordano, L. Shvadchak, V.V. Fauerbach, J.A. Jares-Erijman, E.A. Jovin, T.M. Aprotic media Emission bands Emission shifts Excited-state dipole moment Fluorescence intensities Intramolecular proton-transfer Photo-stability Solvatochromic Solvatochromic properties Stokes shift Alkylation Excited states 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. © 2012 American Chemical Society. Fil:Giordano, L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Fauerbach, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Jares-Erijman, E.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_19487185_v3_n8_p1011_Giordano
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Aprotic media Emission bands Emission shifts Excited-state dipole moment Fluorescence intensities Intramolecular proton-transfer Photo-stability Solvatochromic Solvatochromic properties Stokes shift Alkylation Excited states
spellingShingle	Aprotic media Emission bands Emission shifts Excited-state dipole moment Fluorescence intensities Intramolecular proton-transfer Photo-stability Solvatochromic Solvatochromic properties Stokes shift Alkylation Excited states Giordano, L. Shvadchak, V.V. Fauerbach, J.A. Jares-Erijman, E.A. Jovin, T.M. Highly solvatochromic 7-aryl-3-hydroxychromones
topic_facet	Aprotic media Emission bands Emission shifts Excited-state dipole moment Fluorescence intensities Intramolecular proton-transfer Photo-stability Solvatochromic Solvatochromic properties Stokes shift Alkylation Excited states
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. © 2012 American Chemical Society.
format	JOUR
author	Giordano, L. Shvadchak, V.V. Fauerbach, J.A. Jares-Erijman, E.A. Jovin, T.M.
author_facet	Giordano, L. Shvadchak, V.V. Fauerbach, J.A. Jares-Erijman, E.A. Jovin, T.M.
author_sort	Giordano, L.
title	Highly solvatochromic 7-aryl-3-hydroxychromones
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
url	http://hdl.handle.net/20.500.12110/paper_19487185_v3_n8_p1011_Giordano
work_keys_str_mv	AT giordanol highlysolvatochromic7aryl3hydroxychromones AT shvadchakvv highlysolvatochromic7aryl3hydroxychromones AT fauerbachja highlysolvatochromic7aryl3hydroxychromones AT jareserijmanea highlysolvatochromic7aryl3hydroxychromones AT jovintm highlysolvatochromic7aryl3hydroxychromones
_version_	1782030396568895488

Highly solvatochromic 7-aryl-3-hydroxychromones

Ejemplares similares