Synthesis, crystal structure and photoluminescence of 3-(4-(anthracen-10-yl)phenyl)-benzo[5,6]coumarin.

A new coumarin derivative, 3-(4-(anthracen-10-yl)phenyl)-benzo[5,6]coumarin, was synthesized and characterized by FT-IR, (1)H NMR, element analysis and single crystal X-ray crystallography. The dihedral angle of benzo[5,6]coumarin ring and phenyl group is 36.15 degrees, and the dihedral angle of phenyl group and anthracene skeleton is 89.37 degrees. The UV-vis absorption and photoluminescence of the compound were discussed. The result shown that the compound exhibits high fluorescence quantum yield (Phi(F)), large Stokes shift and green emission (508 nm). The molecular structure of the compound was optimized using density functional theory (DFT) at B3LYP/6-31G(d) level, and the HOMO and LUMO levels of the compound were deduced. Copyright 2009 Elsevier B.V. All rights reserved.