화학공학소재연구정보센터
Molecular Crystals and Liquid Crystals, Vol.623, No.1, 285-296, 2015
Crystal Structure, Hydrogen-Bonding Properties, and DFT Studies of 2-((2-(2-Hydroxyphenyl)benzo[d]thiazol-6-yl)methylene)malononitrile
The title compound, 2-((2-(2-hydroxyphenyl)benzo[d]thiazol-6-yl)methylene)malono-nitrile (1), was synthesized and characterized by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P2(1)/c, with a = 7.4351(8), b = 7.6568(10), c = 24.542(2) angstrom, alpha = 90 degrees, beta = 96.680(9)degrees, alpha nu delta gamma = 90 degrees. Compound 1 possesses a strong intramolecular six-membered-ring hydrogen bond, from which excited-state intramolecular proton transfer takes place, resulting in a proton-transfer tautomer emission of 658nm in ethyl acetate. In the crystal structure, intermolecular C-HN hydrogen bonds lead to the formation of columns along the [010] direction that are connected to one another via intermolecular pi pi interactions, so linking the molecules into a continuous three-dimensional framework. Furthermore, the geometric structures, frontier molecular orbitals and the potential energy curves for 1 in the ground and the first singlet excited state were fully rationalized by density functional theory (DFT) and time-dependent DFT calculations.