(E)-2-(hydroxystyryl)-3-phenylquinazolin-4(3H)-ones: Synthesis, photochemical and luminescent properties

Abstract

The new (E)-2-(hydroxyarilethenyl)-3-phenylquinazolin-4(3H)-ones with various substituents in phenyl fragment were synthesized. The effect of electron donor and acceptor substituents (±M) in quinazolinones on luminescence intensity and dual emission in 550-650-nm wavelength range was shown. The fact of the reversible photo/thermal E-Z isomerization for several substances was established. The (E)-2-(5-chloro-2-hydroxystyryl)-3-phenylquinazolin-4(3H)-one had shown the best combination of photochemical (E-Z isomerization) and photophysical properties. The (E)-2-(2-hydroxy-5-morpholinostyryl)-3-phenylquinazolin-4(3H)-one had revealed the best ESIPT-luminescence (Φrel = 5.3 %).