Quinone–Bodipy H-bonding interaction over π-stacking in toluene

Abstract

Quinone type compounds (o-chloranil, p-chloranil and DDQ) demonstrate excellent H-bonding interactions with a meso-phenol Bodipy dye (1) in both ground and excited state in a non-polar toluene medium. The spectroscopic detection of isosbestic absorption occurs with both quinones and fullerenes, but only quinones form isoemissive complexes with dye 1. ¹H NMR study and Monte Carlo global minima searching justified the above mentioned results with efficiency.