Substituted 2-(2-hydroxyphenyl)-3H-quinazolin-4-ones and their difluoroboron complexes: Synthesis and photophysical properties.

2-(2-Hydroxyphenyl)-3H-quinazolin-4-ones with diverse substituents at phenol ring and their six-membered difluoroboron complexes have been synthesized via few-stage approach. The photophysical properties of target compounds have been investigated in two solvents as well as in the solid state. The nature of substituents and substitution point in the phenol moiety of ligands and resulting BF2-complexes on the photophysical properties of dyes have been explored. The complex bearing two t-Bu groups proved to be the most emissive in solid state, whereas its 5-methoxy and 4-diethylamino counterparts possess strong emission in toluene solution. The dyes exhibited large Stokes shifts which was attributed to excited state intramolecular proton transfer (ESIPT). Additionally, fluorescence of quinazolinones in the mixture of THF/water was studied. All ligands demonstrated emission enhancement with increase of water fraction which was due to aggregation induced emission.