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Synthesis and characterization of 1,3,4-oxadiazole derivatives containing alkoxy chains with different lengths

✍ Scribed by Xiao-bing Zhang; Ben-chen Tang; Peng Zhang; Min Li; Wen-jing Tian


Publisher
Elsevier Science
Year
2007
Tongue
English
Weight
521 KB
Volume
846
Category
Article
ISSN
0022-2860

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✦ Synopsis


The synthesis, optical properties, electrochemical properties, electronic structures and applications in electroluminescent device of three series of 1,3,4-oxadiazole derivatives, 1,4-bis[(4-methylphenyl)-1,3,4-oxadiazolyl]phenylene (OXD 1 ), 5,5 0 -di-(4-methyl)-2,2 0 -p-(2,5-bisalkoxyphenylene)-bis-1,3,4-oxadiazole (OXD 2-n ) and 1,4-bis[(4-alkoxyphenyl)-1,3,4-oxadiazolyl]phenylene (OXD 3-n ) are reported. The molecular structures of the oxadiazole compounds were confirmed by FT-IR, 1 H NMR spectroscopy and elemental analysis. The optical and electrochemical properties of the compounds were investigated by UV-vis absorption and photoluminescence spectroscopy as well as cyclic voltammetry. The results show that introduction of two alkoxy groups whose electron-donating ability is stronger than that of methyl groups increases the electron density of the conjugated segment of OXD 2-n (with side-on alkoxy substituents) and OXD 3-n (with end-on alkoxy substituents), and thus leads to the absorption maximum bathochromic-shift compared to that of OXD 1 . The HOMO and LUMO energy levels of the compounds studied are in the range of Γ€2.78 to Γ€2.89 and Γ€5.75 to Γ€6.20 eV. Calculations on the representative compounds by the Dmol 3 package of MS Modeling 3.0 revealed that the increase of energy levels in both OXD 2-n and OXD 3-n was due to the change of the frontier molecular orbital distribution in the central benzene ring. The light-emitting devices have been fabricated using blends of MEH-PPV and these compounds as emissive layers, among which, maximum brightness up to 11810 cd m Γ€2 (8.5 V) has been observed, which is 40 times brighter than that with MEH-PPV. The result of the devices suggested that oxadiazole derivatives studied function well as electron-transporting materials and can be used in LEDs, and thus to enhance the efficiency of LEDs.


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