Synthesis, photophysical and solvatochromic properties of diacetoxyboron complexes with curcumin derivatives

Five novel diacetoxyboron complexes of beta-diketones incorporated curcumin moiety were designed and synthesized. Their photophysical behaviors were investigated by UV-vis absorption and fluorescence spectroscopy in different solvents and solid state. It was observed that their fluorescence spectra yielded a blue to yellow-green emission in solution and emitted a yellow to red emission in solid state. Especially, the complex 3b displayed the strongest emission and the highest quantum efficiency (Phi(u)=0.98) in toluene among these complexes. The CIE coordinate of the complex 3b in solid state was positioned in an ideal red region of the chromaticity diagram. The maximal emission of these complexes exhibited a large wavelength shift and Stokes shift increased with the increase of the solvent polarity. Their dipole moment differences between the ground and excited states were also estimated by using the Lippert-Mataga equation. Meanwhile, their HOMO, LUMO energy levels and energy band gaps were calculated by cyclic voltammetry. (C) 2019 Elsevier B.V. All rights reserved.