Highly Solvatochromic 7-Aryl-3-hydroxychromones

作者：Giordano Luciana^*; Shvadchak Volodymyr V; Fauerbach Jonathan A; Jares Erijman Elizabeth A; Jovin Thomas M

来源：Journal of Physical Chemistry Letters, 2012, 3(8): 1011-1016.

DOI：10.1021/jz3002019

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 (%26gt;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 %26gt;40 nm spread in the emission band position.

• 出版日期2012-4-19