Spectroscopic Properties of Morin in Various CH3OH–H2O and CH3CN–H2O Mixed Solvents

The specific fluorescence properties of morin (3,2′,4′,5,7‐pentahydroxyflavone) were studied in various CH₃OH–H₂O and CH₃CN–H₂O mixed solvents. Although the dihedral angle is large in the S₀ state, morin has an almost planar molecular structure in the S₁ state owing to the very low rotational energy barrier around the interring bond between B and the A, C ring. The excited state intramolecular proton transfer (ESIPT) at the S₁ state cannot occur immediately after excitation, S₁ → S₀ fluorescence can be observed. Two conformers, Morin A and B have been known. At the CH₃OH–H₂O, Morin B will be the principal species but at the CH₃CN–H₂O, Morin A is the principal species. At the CH₃OH–H₂O, owing to the large Franck–Condon (FC) factor for S₂ → S₁ internal convernal (IC) and flexible molecular structure, only S₁ → S₀ fluorescence was exhibited. At the CH₃CN–H₂O, as the FC factor for S₂ → S₁ IC is small and molecular structure is rigid, S₂ → S₀ and S₁ → S₀ dual fluorescence was observed. This abnormal fluorescence property was further supported by the small pK₁ value, effective delocalization of the lone pair electrons of C(2′)–OH to the A, C ring, and a theoretical calculation.