Synthesis and characterization of 1,3,4-oxadiazole-triazolopyridinone hybrid derivatives as new blue-greenish photoluminescent materials

✍ Scribed by Kuo-Chen Chiang; Fung Fuh Wong; Chih-Shiang Chang; Mann-Jen Hour; Yu-Ling Wang; Shaw-Bing Wen; Mou-Yung Yeh

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2007
• Tongue: English
• Weight: 409 KB
• Volume: 44
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570440313

✦ Synopsis

Abstract

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Recently, New functionalized oxadiazole‐triazolopyridinone hybrid compounds were investigated as photoluminescent materials. In this work, we introduce triazolopyridinone to synthesize a series of oxadiazole‐triazolopyridinone hybrid derivatives as potential photoluminescent materials and explore the effect of modification of the triazolopyridinone moiety. The λ~max~ values of the photoluminescence (PL) spectra of 1,3,4‐oxadiazole‐triazolopyridinone hybrids are promoted to longer wavelengths (470‐486 nm) than the traditional 1,2,3‐triazole derivatives (410‐425 nm) in solutions. PL spectra 5a, 5d, and 5g of the vacuum evaporated films on quartz substrates, with a maximum at 487 nm, shows a red‐shift (∼15‐20 nm), with respect to the solution spectrum. The solution fluorescence quantum yields (Φ~f~) 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 (Φ~f~ = 0.80). 1,3,4‐Oxadiazole‐triazolopyridinone hybrid derivatives show clearly non‐reversible reduction processes in cyclic voltammogram measurements. Following spectroscopic studies and observation of the electrochemical behaviors, 1,3,4‐oxadiazole‐triazolopyridinone derivatives were determined to be potential efficient bluegreenish photoluminescent materials.