Synthesis and Characterization of Potential Efficient Electroluminescent Materials: 2-Phenyl-5-[4-(4-phenylamino-2H-1,2,3-triazol-2-yl)]phenyl-1,3,4-oxadiazole Derivatives

Abstract

Abstract Recently, 1,3,4-oxadiazole-based on heterocyclic compounds were investigated as electroluminescent materials. In this work, we first introduce 1,2,3-triazole to synthesize a series of 1,3,4-oxadiazole–1,2,3-triazole hybrids derivatives as potential electroluminescent materials and explore the effect of modification of the 1,2,3-triazole moiety. The λmax values of the UV–vis of 1,3,4-oxadiazole–1,2,3-triazole hybrids are promoted to longer wavelengths (340–350 nm) than the traditional 1,2,3-triazole derivatives (280–330 nm) in solutions and have a bathochromic shift to 350–360 nm in THF solution. The λmax values of the photoluminescence (PL) spectra are in the range 406–480 nm in solutions. Compound 7h evaporated to form films on quartz substrates, had a maximum at 455 nm and showed a red-shift (≈40 nm) with respect to the solution spectrum. The solution fluorescence quantum yields (Φf) were measured, all of which fell into the range 0.65–0.76, and were determined relative to that of 2-phenyl-5-(4-biphenyl)-1,3,4-oxadiazole in benzene (Φf = 0.80). 1,3,4-Oxadiazole–1,2,3-triazole hybrids derivatives show unclearly reversible reduction processes in cyclic voltammogram measurements. Following spectroscopic studies and observation of the electrochemical behaviors, 1,3,4-oxadiazole–1,2,3-triazole derivatives were determined to be highly potential efficient blue electroluminescent materials.