Synthesis and characterization of 1,3,4-oxadiazole derivatives containing alkoxy chains with different lengths
β 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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β¦ 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 Γ2.78 to Γ2.89 and Γ5.75 to Γ6.20 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 Γ2 (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.
π SIMILAR VOLUMES
## Abstract Six 1,3,4βoxadiazoleβcontaining polyethers with reduced viscosities of 0,65β1,17 dL Β· g^β1^ were synthesized by highβtemperature solution polycondensation of an activated difluoride, 2,5βbis(4βfluorophenyl)β1,3,4βoxadiazole, with aromatic diols possessing a variety of ring structures. T
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