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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 08: 1479 - 1486

DOI: https://doi.org/10.6023/cjoc1112291

Articles

Synthesis, Crystal Structure and Properties of Iodide and Hexafluorophosphate Salts of 2-Ferrocenyl (or Binuclear Ferrocenyl)-1,3-dialkylbenzimidazolium

  • Wang Jing ,
  • Feng Limin ,
  • Ma Feijuan ,
  • Lin Fen ,
  • Xie Lili ,
  • Yuan Yaofeng
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  • a Fujian Provincial Key Laboratory of Photocatalysis-State Key Laboratory Breeding Base, Fuzhou University, Fuzhou 350108;
    b Department of Chemistry, Fuzhou University, Fuzhou 350108;
    c Instrumental Measurement & Analysis Center, Fuzhou University, Fuzhou 350108

Received date: 2011-12-29

  Revised date: 2012-03-11

  Online published: 2012-04-11

Supported by

Project supported by the Natural Science Foundation of Fujian Province of China (Nos. 2010J01036, 2009J05028) and the Key Program of Science and Technology of Fujian Province of China (No. 2009H0021).

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Abstract

Iodide salt 4 and hexafluorophosphate salt 5 of 1-methyl-2-ferrocenyl-3-ethylbenzimidazolium are prepared using 2-ferrocenylbenzimidazole 2 as starting material. 2-[1'-(2-Ferrocenylpropan-2-yl)ferrocen-1-yl]benzimidazole (7) is obtained by the reaction of formyl 2,2-diferrocenylpropane with o-diaminobenzene in the condition of methanol as solvent, reflux and catalysis of iodine. Iodide salt 9 and hexafluorophosphate salt 10 of 1-methyl-2-[1'-(2-ferrocenylpropan-2-yl)-ferrocen-1- yl]-3-ethylbenzimidazolium are synthesized using 7 as starting material. Oxidative potentials of ferrocenyl connected directly to benzimidazolium in these salts move to more positive position to a large extent. Crystal structure of 4 is explained and π-π stacking is showed. UV-Vis spectra shows that photoinduced charge transfer exists for salts. Iodide salt 4 presents good catalytic effect on decomposition of ammonium perchlorate (AP) in DSC-TG (differential scanning calorimetry- thermogravimetric) test.

Key words： ferrocene; binuclear ferrocenyl; benzimidazolium

Cite this article

Wang Jing , Feng Limin , Ma Feijuan , Lin Fen , Xie Lili , Yuan Yaofeng . Synthesis, Crystal Structure and Properties of Iodide and Hexafluorophosphate Salts of 2-Ferrocenyl (or Binuclear Ferrocenyl)-1,3-dialkylbenzimidazolium[J]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1479 -1486 . DOI: 10.6023/cjoc1112291

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