Abstract:
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.
Registro:
Documento: |
Artículo
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Título: | Highly solvatochromic 7-aryl-3-hydroxychromones |
Autor: | Giordano, L.; Shvadchak, V.V.; Fauerbach, J.A.; Jares-Erijman, E.A.; Jovin, T.M. |
Filiación: | Laboratory for Cellular Dynamics, Max Planck Institute for Biophysical Chemistry, Am Faßberg 11, Göttingen, Germany Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
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Palabras clave: | 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 |
Año: | 2012
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Volumen: | 3
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Número: | 8
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Página de inicio: | 1011
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Página de fin: | 1016
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DOI: |
http://dx.doi.org/10.1021/jz3002019 |
Título revista: | Journal of Physical Chemistry Letters
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Título revista abreviado: | J. Phys. Chem. Lett.
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ISSN: | 19487185
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_19487185_v3_n8_p1011_Giordano |
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Citas:
---------- APA ----------
Giordano, L., Shvadchak, V.V., Fauerbach, J.A., Jares-Erijman, E.A. & Jovin, T.M.
(2012)
. Highly solvatochromic 7-aryl-3-hydroxychromones. Journal of Physical Chemistry Letters, 3(8), 1011-1016.
http://dx.doi.org/10.1021/jz3002019---------- CHICAGO ----------
Giordano, L., Shvadchak, V.V., Fauerbach, J.A., Jares-Erijman, E.A., Jovin, T.M.
"Highly solvatochromic 7-aryl-3-hydroxychromones"
. Journal of Physical Chemistry Letters 3, no. 8
(2012) : 1011-1016.
http://dx.doi.org/10.1021/jz3002019---------- MLA ----------
Giordano, L., Shvadchak, V.V., Fauerbach, J.A., Jares-Erijman, E.A., Jovin, T.M.
"Highly solvatochromic 7-aryl-3-hydroxychromones"
. Journal of Physical Chemistry Letters, vol. 3, no. 8, 2012, pp. 1011-1016.
http://dx.doi.org/10.1021/jz3002019---------- VANCOUVER ----------
Giordano, L., Shvadchak, V.V., Fauerbach, J.A., Jares-Erijman, E.A., Jovin, T.M. Highly solvatochromic 7-aryl-3-hydroxychromones. J. Phys. Chem. Lett. 2012;3(8):1011-1016.
http://dx.doi.org/10.1021/jz3002019