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

被引:2
作者
Chiang, Kuo-Chen
Wong, Fung Fuh
Chang, Chih-Shiang
Hour, Mann-Jen
Wang, Yu-Ling
Wen, Shaw-Bing
Yeh, Mou-Yung
机构
[1] China Med Univ, Grad Inst Pharmaceut Chem, Taichung 40402, Taiwan
[2] China Med Univ, Sch Pharm, Taichung 40402, Taiwan
[3] Natl Cheng Kung Univ, Dept Chem, Tainan 70101, Taiwan
[4] Natl Cheng Kung Univ, Dept Resources Engn, Tainan 70101, Taiwan
[5] Natl Cheng Kung Univ, Sustainable Environm Res Ctr, Tainan 709, Taiwan
关键词
D O I
10.1002/jhet.5570440313
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 X.., values of the photoluminescence (PL) spectra of 1,3,4-oxadiazole-triazolopyridinone hybrids are promoted to longer wavelengths (470486 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 redshift (similar to 15-20 nm), with respect to the solution spectrum. The solution fluorescence quantum yields (Phi(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 (Phi(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 blue-greenish photoluminescent materials.
引用
收藏
页码:591 / 596
页数:6
相关论文
共 30 条
[1]   BLUE LIGHT-EMITTING ORGANIC ELECTROLUMINESCENT DEVICES [J].
ADACHI, C ;
TSUTSUI, T ;
SAITO, S .
APPLIED PHYSICS LETTERS, 1990, 56 (09) :799-801
[2]   CONFINEMENT OF CHARGE-CARRIERS AND MOLECULAR EXCITONS WITHIN 5-NM-THICK EMITTER LAYER IN ORGANIC ELECTROLUMINESCENT DEVICES WITH A DOUBLE HETEROSTRUCTURE [J].
ADACHI, C ;
TSUTSUI, T ;
SAITO, S .
APPLIED PHYSICS LETTERS, 1990, 57 (06) :531-533
[3]  
Chan LH, 2001, ADV MATER, V13, P1637, DOI 10.1002/1521-4095(200111)13:21<1637::AID-ADMA1637>3.0.CO
[4]  
2-S
[5]   Syntheses and spectroscopic studies of spirobifluorene-bridged bipolar systems; photoinduced electron transfer reactions [J].
Chien, YY ;
Wong, KT ;
Chou, PT ;
Cheng, YM .
CHEMICAL COMMUNICATIONS, 2002, (23) :2874-2875
[6]   Studies on the reaction of α-chloroformylarylhydrazine hydrochloride with N-heterocyclic compounds [J].
Chiu, CY ;
Kuo, CN ;
Kuo, WF ;
Yeh, MY .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2002, 49 (02) :239-249
[7]  
DEMAS JN, 1971, J PHYS CHEM-US, V75, P991, DOI 10.1021/j100678a001
[8]   SYNTHETIC TUBERCULOSTATS .8. ACYL DERIVATIVES OF ISONICOTINYL HYDRAZINE [J].
FOX, HH ;
GIBAS, JT .
JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (10) :1375-1379
[9]   Effect of modifications of the Alkylpiperazine moiety of trazodone on 5HT2A and α1 receptor binding affinity [J].
Giannangeli, M ;
Cazzolla, N ;
Luparini, MR ;
Magnani, M ;
Mabilia, M ;
Picconi, G ;
Tomaselli, M ;
Baiocchi, L .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (03) :336-345
[10]   High-performance blue electroluminescent devices based on 2-(4-biphenylyl)-5-(4-carbazole-9-yl)phenyl-1,3,4-oxadiazole [J].
Guan, M ;
Bian, ZQ ;
Zhou, YF ;
Li, FY ;
Li, ZJ ;
Huang, CH .
CHEMICAL COMMUNICATIONS, 2003, (21) :2708-2709