Journal
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
Volume 3, Issue 8, Pages 1011-1016Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jz3002019
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- Max Planck Society
- Marie Curie Actions
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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 similar to 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.
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