Acta Phys. -Chim. Sin. ›› 2010, Vol. 26 ›› Issue (12): 3310-3316.doi: 10.3866/PKU.WHXB20101201

• PHOTOCHEMISTRY AND SPECTROSCOPY • Previous Articles     Next Articles

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

QI Zheng-Jian, WEI Bin, WANG Xue-Mei, KANG Feng, HONG Man-Xin, TANG Lan-Lan, SUN Yue-Ming   

  1. College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P. R. China
  • Received:2010-07-15 Revised:2010-08-24 Published:2010-12-01
  • Contact: QI Zheng-Jian, SUN Yue-Ming E-mail:qizhengjian@seu.edu.cn, sun@seu.edu.cn
  • Supported by:

    The project was supported by the National Natural Science Foundation of China (21075015) and Jiangsu Province Science and Technology Support Program, China (BE 2009150).

Abstract:

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.

Key words: Functional optoelectronic material, Alkyloxypolythiophene, Oxadiazole, Donor, Acceptor

MSC2000: 

  • O649