Synthesis, X-ray crystal structure and optical properties of novel 2,5-diaryl-1, 3,4-oxadiazole derivatives containing substituted pyrazolo[1,5-a]pyridine units

A series of pyrazolo[1,5-alpyridine-containing 2,5-diaryl-1,3,4-oxadiazole derivatives were synthesized and their structures were characterized by IR, H-1 NMR and HRMS spectra. The crystal structure of 3a was determined using single crystal X-ray crystallography. Its spatial structure was found to be monoclinic, and all aromatic rings were approximately coplanar, which allowed conjugation. The absorption results showed that compounds 1a-f presented their absorption peaks ranging from 264 nm to 290 nm, while compounds 3a-f with a larger conjugation system exhibited red-shifted absorption character (absorption maxima between 283 nm and 303 nm) compared to the corresponding absorption of 1-af. Fluorescence spectra revealed that these compounds exhibited blue fluorescence (421-444 nm) in dilute solutions and showed quantum yields of fluorescence between 0.32 and 0.83 in dichloromethane. (C) 2011 Elsevier Ltd. All rights reserved.