A series of new
Schiff bases containing the phenyl-ethynyl-phenyl system was synthesized and their thermal stability, photophysical and electrochemical properties were investigated. Moreover, DFT calculations were performed to obtain the optimized ground-state geometry and distribution of the HOMO and LUMO levels as well as IR spectra of the prepared compounds. It was found that, the photoluminescence of synthesized
imines was negligible in all investigated organic
solvents except for the PBS/
ACN mixture. As was proved in further studies, this phenomenon was related to the partial hydrolysis of
imines, which is the source of the fluorogenic
aldehyde causing the aggreggacion incrased-emision effect. In further research, due to the susceptibility of the azomethines to partial hydrolysis, the
biological activity of 2-{(E)-[4-(phenylethynyl) phenyl]imino}
phenol (1b), substrate (2-aminophenol) and Cu(II)-1b complex was analyzed. The
biological tests showed, that 1b (as example of
imine resveratrol analogue), demonstrated its increased
cytostatic activity in
prostate cancer cellular system. It was proved that the non-hydrolyzed
imine was crucial for the cytotoxic effect. This activity could be ascribed to its Cu(II) complexing capability as showed in our previous research.