Citation: QI Zheng-Jian, WEI Bin, WANG Xue-Mei, KANG Feng, HONG Man-Xin, TANG Lan-Lan, SUN Yue-Ming. Synthesis, Optical and Electrochemical Properties of Novel 3,4-Dialkyloxythiophene-Based D-A-D Organic Conjugated Molecules[J]. Acta Physico-Chimica Sinica, ;2010, 26(12): 3310-3316. doi: 10.3866/PKU.WHXB20101201 shu

Synthesis, Optical and Electrochemical Properties of Novel 3,4-Dialkyloxythiophene-Based D-A-D Organic Conjugated Molecules

1.
College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P. R. China

Received Date: 15 July 2010
Available Online: 22 October 2010
Fund Project: 国家自然科学基金(21075015) (21075015)江苏省科技支撑项目(BE 2009150)资助 (BE 2009150)

Novel 3,4-dialkyloxythiophene-based D-A-D organic conjugated molecules di(2-vinyl-3,4- dialkyloxythiophene)-p-2,5-bisphenyl-1,3,4-oxadiazole [(3,4DAOTV)₂-OXD] were obtained using the Wittig reaction. The structure was effectively characterized using hydrogen nuclear magnetic resonance (¹H NMR), Fourier transform infrared (FTIR) spectroscopy, high pressure liquid chromatography (HPLC) and elemental analysis (EA). The optical and electrochemical properties were studied by UV-Vis, fluorescence spectroscopy, and cyclic voltammetry. The UV-Vis maximum absorption of the three studied compounds ranged between 382-383 nm and their optical bandgaps ranged from 2.92 to 2.97 eV. Their emission maxima ranged from 448 to 452 nm with a bright cyan light and their luminescence quantum yields ranged from 36.8%-37.6% in CHCl₃. As solid films, these compounds emit glaucous light at 513-516 nm. The (3, 4DAOTV)₂-OXDs show oxidation and reduction processes in their cyclic voltammograms. Their ionization potentials of 5.65-5.70 eV coincide with the hole transport ability of thiophenes and their electron affinity values of 2.74-2.88 eV are close to the required properties of an electron transport material. These properties will facilitate electron injection and transfer from the cathode. Theoretical calculations indicate that the D-A-D organic conjugation molecule has high coplanarity and that electrons are delocalized along its backbone, which might result in interfacial molecular self-assembly and efficient charge carrier transport as well as efficient quantum yields of devices.
- Functional optoelectronic material,
- Alkyloxypolythiophene,
- Oxadiazole,
- Donor,
- Acceptor
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