Synthesis of new substituted benzaldazine derivatives, hydrogen bonding-induced supramolecular structures and luminescent properties

摘要

Syntheses of three benzaldazine compounds 1-3 with the general formula Ar1(CH = N-N = HC)Ar2 (Ar1=Ar2 = 2-OH-3,5-~tBu2C6H2 (1), Ar1 = Ar2 = 2-BrC6H4 (2), Ar1=ortho-C6H4(NHC6H3-Me2-2,6), Ar2 = C6H4F-2 (3)) are described. All compounds were characterized by elemental analysis, ~1H NMR, ~(13)C NMR, IR spectroscopy and single-crystal X-ray crystallography. The different supramolecular structures were obtained through different weak interactions (C-H···O, O-H···N and π···π interactions for 1; C-H···Br and Br···Br interactions for 2; C - H···F and C - H···N interactions for 3). Compound 1 shows solvent-dependent fluorescent properties with blue to green emission on the increasing of the solvent polarity. Compounds 2, 3 show blue photoluminescence in different solvents.