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Acta Chimica Sinica >

2012 , Vol. 70 >Issue 06: 721 - 727

DOI: https://doi.org/10.6023/A1111022

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Theoretical Study of Synthesis Mechanism and Electronic Structure for 3-Octylthien-2,5-ylenediethynylene-co-benzo[c]-1',2',5'- thiadiazo-3,6-ylenedi(2,5-thienylene)

  • Zhang Fulan ,
  • Wan Bangjiang ,
  • Xu Bohua ,
  • Huang Huisheng
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  • College of Chemistry and Chemical Engineering, Yangtze Normal University, Fuling, Chongqing 408003

Received date: 2011-11-02

  Revised date: 2011-11-30

  Online published: 2011-12-22

Supported by

Project supported by the Natural Science Foundation of Education Committee of Chongqing (No. KJ091311).

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Abstract

The synthesis mechanism of 3-octylthien-2,5-ylenediethynylene-co-benzo[c]-1',2',5'-thiadiazo- 3,6-ylenedi(2,5-thienylene) with PdCl2(PPh3)2-catalyzed is investigated by density functional theory (DFT) at the GGA/PW91/DNP level. The geometric configurations of reactants, intermediates, transition states, and products are optimized. The energy analysis calculation approves the authenticity of intermediates and transition states. Additionally, the synthesis mechanism of 3-octylthien-2,5-ylenediethynylene-co-benzo[c]- 1',2',5'-thiadiazo-3,6-ylenedi(2,5-thienylene) without PdCl2(PPh3)2-catalyzed is studied employing the same functional and basis set. The computational results show that the activation barrier with PdCl2(PPh3)2- catalyzed is lower than the activation barrier without PdCl2(PPh3)2-catalyzed, which demonstrates that the catalyst of PdCl2(PPh3)2 possesses catalytic activity. Moreover, the density functional theory and periodic slab model are used to investigate the product (P) adsorption on TiO2(100) surface. The Mulliken charge and frontier orbital of the TiO2(100)-P are also discussed. The results reveal that the charge of 0.692 e transfers from the P to the TiO2(100) surface and the energy gap becomes narrow when the adsorption occurs. It is found that the above-mentioned theoretical calculations agree well with the experiment results.

Key words： 3-octylthien-2,5-ylenediethynylene-co-benzo[c]-1',2',5'-thiadiazo-3,6-ylenedi(2,5-thienylene); density functional; synthesis mechanism; electronic structure

Cite this article

Zhang Fulan , Wan Bangjiang , Xu Bohua , Huang Huisheng . Theoretical Study of Synthesis Mechanism and Electronic Structure for 3-Octylthien-2,5-ylenediethynylene-co-benzo[c]-1',2',5'- thiadiazo-3,6-ylenedi(2,5-thienylene)[J]. Acta Chimica Sinica, 2012 , 70(06) : 721 -727 . DOI: 10.6023/A1111022

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