Synthesis, structure and spectral properties of 9-diarylamino-substituted acridines

The synthesis of three 9-diarylamino-substituted acridines is reported. The compounds of the donor–acceptor type – N,N-diphenylacridin-9-amine (1), 2,7-dimethyl-N,N-bis(4-methylphenyl)acridin-9-amine (2), and 2,7-bis(1-methyl-1-phenylethyl)-N,N-bis[4-(1-methyl-1-phenylethyl)phenyl]acridin-9-amine (3) were characterized by IR, 1H and 13C NMR, mass-spectral and elemental analysis. The crystal structures of compounds 1–3 and their protonated forms were determined by X-ray diffraction analysis. The absorption and fluorescence spectra were measured in various solvents. Solvatochromic shifts and dependence of the fluorescence quantum yields on the solvent polarity and protonation suggest the use of these compounds as chemical sensors. An example of a sensor material based on compound 2 is presented. Density functional theory calculations of the structures and time-dependent density functional theory calculations of the gas-phase excitation and emission energies of 1 were performed at the PBE0/SVP level of theory.