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Journal Article

Highly solvatochromic 7-aryl-3-hydroxychromones.

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Giordano,  L.
Emeritus Group Laboratory of Cellular Dynamics, MPI for biophysical chemistry, Max Planck Society;

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Shvadchak,  V. V.
Emeritus Group Laboratory of Cellular Dynamics, MPI for biophysical chemistry, Max Planck Society;

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Jovin,  T. M.
Emeritus Group Laboratory of Cellular Dynamics, MPI for biophysical chemistry, Max Planck Society;

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Citation

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, 1011-1016. doi:10.1021/jz3002019.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-83B6-5
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-hydrox- ychromones 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.