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Three aryl and three naphthylmethylene derivatives containing thiadiazole ring have been synthesized. The structures of target compounds were characterized on the basis of spectral (FT-IR, 1H NMR, and MS). The optical properties were detected using UV-vis absorption spectroscopy and fluorescence spectroscopy. The absorption spectra of 1a, 2a and 3a substituted by naphthylmethylene are primarily characterized by a peak around 284 nm originating from naphthalene, which is different from that of compounds 1b, 2b and 3b. Compared to 1a and 2a (separated by a saturable atomic cluster −CH2−), the maximum absorption wavelength of 1b and 2b takes on obvious red-shifted, which is from thiadiazole and benzene with more large conjugated system. The fluorescence intensity of 2-(4-aminobenzoyl) amide-5-naphthylmethylene-1,3,4-thiadiazole (3a) was significantly higher than that of 5-(4-aminobenzoyl)-1,3,4-thiadiazole (3b) due to the presence of naphthalene.

Asymmetric 2-p-nitrophenyl-5-naphthylmethylene-1,3,4-oxadiazole and 2-p-aminophenyl-5-naphthylmethylene-1,3,4-oxadiazole were synthesized and characterized by IR、1HNMR and MS analysis, and their optical properties were detected using UV-vis absorption spectroscopy and fluorescence spectroscopy. The existence of electron-withdrawing oxadiazole units causes a significant bathochromic shift of the UV absorption maximum. The largest UV-absorption peak of target compounds is in the range of 298-317 nm, and a new emission band at 402 nm is formed. The fluorescence intensity is gradually enhanced, which strengthens the intramolecular charge transfer effect between the electron-withdrawing oxadiazole and electron-donating aniline.