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 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.
†Laboratory for Cellular Dynamics, Max Planck Institute for Biophysical Chemistry, Am Faßberg 11, Göttingen, Germany.
Luciana
L
Giordano
†Laboratory for Cellular Dynamics, Max Planck Institute for Biophysical Chemistry, Am Faßberg 11, Göttingen, Germany.
Volodymyr V
VV
Shvadchak
‡Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina.
Jonathan A
JA
Fauerbach
‡Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina.
Elizabeth A
EA
Jares-Erijman
†Laboratory for Cellular Dynamics, Max Planck Institute for Biophysical Chemistry, Am Faßberg 11, Göttingen, Germany.
Thomas M
TM
Jovin
ESIPT; Prodan; environment-sensitive; fluorescence; liposomes; probe