Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (04): 827-834.DOI: 10.6023/cjoc201301036 Previous Articles     Next Articles

Articles

1-二茂铁基甲基-2-二茂铁基-3-烷基苯并咪唑盐的合成、晶体结构及性质研究

叶宏民a,b, 王薇a,b, 朱晓晓a,b, 陈伟强a,b, 谢莉莉a,b, 袁耀锋a,b   

  1. a 福建省光催化重点实验室——省部共建国家重点实验室培育基地 福州 350108;
    b 福州大学化学系 福州 350108
  • 收稿日期:2013-01-15 修回日期:2013-03-01 发布日期:2013-03-14
  • 通讯作者: 谢莉莉 E-mail:xielili@fzu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21202019, 21172036)、国家基础科学人才培养基金(No. J1103303)以及教育部留学回国人员科研启动基金(No. 教外司留[2011]1568号)资助项目.

Synthesis Crystal Structure and Properties of Iodide, Hexafluoro- phosphate and Bis(trifluoromethane sulfonamide) Salts of 1-Ferrocenyl Methyl-2-ferrocenyl-3-alklybenzimidazolium

Ye Hongmina,b, Wang Weia,b, Zhu Xiaoxiaoa,b, Chen Weiqianga,b, Xie Lilia,b, Yuan Yaofenga,b   

  1. a Fujian Provincial Key Laboratory of Photocatalysis-State Key Laboratory Breeding Base, Fuzhou University, Fuzhou 350108;
    b Department of Chemistry, Fuzhou University, Fuzhou 350108
  • Received:2013-01-15 Revised:2013-03-01 Published:2013-03-14
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21202019, 21172036), the National Science Foundation for Fostering Talents in Basic Research of China (No. J1103303) and the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry (No. [2011]1568).

1-Ferrocenly methyl-2-ferrocenly benzimidazole was sythesized by the reaction of o-phenylenediamine with ferrocenecarboxaldehyde in the condition of toluenesulfonic acid as catalyst. Iodized salts (3, 4) of 1-ferrocenyl methyl- 2-ferrocenyl-3-alkylbenzimidazolium were formed by the reaction of compound 2 with alkyl iodide. Hexafluorophosphate salts (5, 6) and bis(trifluoromethane sulfonimide) salts (7, 8) of 1-ferrocenyl methyl-2-ferrocenyl-3-alkylbenzimidazolium were obtained by the anion exchange reaction of compounds 3 and 4. All of these salts were characterized by 1H NMR, 13C NMR, IR, MS, HRMS and elemental analysis. In the crystal of compound 5, the compound was assembled to a chain supramolecular structure along axis c by the intermolecular hydrogen bonds. Electrochemical analysis demonstrated that the quasi-reversible oxidation waves split double of Fe in ferrocene fragment of compounds 38; UV-Vis absorption spectra show that these salts possess photoinduced charge migration phenomenon. And the iodized salts presented good catalytic effect on decomposition of ammonium perchlorate (AP) in DSC-TG test.

Key words: ferrocene, benzimidazolium, crystal structure, ammonium perchlorate, thermal decomposition