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2013 , Vol. 33 >Issue 04: 827 - 834

DOI: https://doi.org/10.6023/cjoc201301036

研究论文

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 ,
  • 王薇 ,
  • 朱晓晓 ,
  • 陈伟强 ,
  • 谢莉莉 ,
  • 袁耀锋
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  • 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

  网络出版日期: 2013-03-14

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.

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

  • Ye Hongmin ,
  • Wang Wei ,
  • Zhu Xiaoxiao ,
  • Chen Weiqiang ,
  • 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

Received date: 2013-01-15

  Revised date: 2013-03-01

  Online 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).

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摘要

以二茂铁甲醛为原料, 在对甲苯磺酸催化下, 与邻苯二胺缩合得到1-二茂铁基甲基-2-二茂铁基苯并咪唑(2), 化合物2与碘代烷进行烷基化反应得到1-二茂铁基甲基-2-二茂铁基-3-烷基苯并咪唑碘盐(3, 4), 并通过阴离子交换反应得到1-二茂铁基甲基-2-二茂铁基-3-烷基苯并咪唑六氟磷酸盐(5, 6)及双三氟甲磺酰亚胺盐(7, 8). 利用1H NMR, 13C NMR, IR, MS, HRMS及元素分析对所有产物进行结构表征. 化合物5的单晶结构表明该化合物通过分子间氢键作用自组装成了沿c轴无限延伸的一条链状超分子结构. 电化学分析表明化合物3～8中的Fe1与Fe2由原来的一组氧化还原峰分离成了两组氧化还原峰. UV-Vis吸收光谱曲线表明所有产物具有光致电荷迁移现象. DSC-TG(差示扫描量热-热重)曲线显示所得碘盐化合物对高氯酸铵(AP)热分解有较好的催化效果.

关键词： 二茂铁; 苯并咪唑盐; 晶体结构; 高氯酸铵; 热分解

本文引用格式

叶宏民 , 王薇 , 朱晓晓 , 陈伟强 , 谢莉莉 , 袁耀锋 . 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[J]. 有机化学, 2013 , 33(04) : 827 -834 . DOI: 10.6023/cjoc201301036

Abstract

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 3～8; 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

参考文献

[1] Subramanian, K. J. Polym. Sci. Part A: Polym. Chem. 1999, 37, 4090.

[2] Wang, Y. X.; Bian, Z. X.; Zhao, Q. H.; Zhai, L. Y.; Yu, H. J.; Yun, Q. Chin. J. Appl. Chem. 2002, 19, 950 (in Chinese).
(王艳学, 边占喜, 赵庆华, 翟林益, 于海军, 云青, 应用化学, 2002, 19, 950.)

[3] Tang, S. Q.; Ding, H. X. Chem. Propellants Polym. Mater. 2004, 2, 8 (in Chinese).
(唐松青, 丁宏勋, 化学推进剂与高分子材料, 2004, 2, 8).

[4] Zhang, Y.; Gao, G. X.; Han, T. T.; Zheng, Y. S. Chem. Propellants Polym. Mater. 2011, 9, 78 (in Chinese).
(张岩, 高国新, 韩婷婷, 郑元锁, 化学推进剂与高分子材料, 2011, 9, 78.)

[5] Yu, H.; Wang, L.; Huo, J.; Ding, J.; Tan, Q. J. Appl. Polym. Sci. 2008, 110, 1594.

[6] Xiao, F. J.; Shi, M. M.; Peng, L.; Luo, Y. J.; Zhao, J. C. J. Inorg. Organomet. Polym. Mater. 2011, 21, 175.

[7] Xiao, F. J.; Sun, X. A.; Wu, X. F.; Zhao, J. C.; Luo, Y. J. J. Organomet. Chem. 2012, 713, 96.

[8] Saravanakumar, D.; Sengottuvelan, N.; Narayanan, V.; Kandaswamy, M.; Varghese, T. L. J. Appl. Polym. Sci. 2011, 119, 2517.

[9] Gao, Y.; Li, H.-D.; Ke, C.-F.; Xie, L.-I.; Wei, B.; Yuan, Y.-F. Appl. Organomet. Chem. 2011, 25, 407.

[10] Gao, Y.; Li, H. D.; Ke, C. F.; Xie, L. L.; Yuan, Y. F. Chem. Propellants Polym. Mater. 2010, 8, 34 (in Chinese).
(高勇, 李恒东, 柯成锋, 谢莉莉, 袁耀锋, 化学推进剂与高分子材料, 2010, 8, 34.)

[11] Liao, W. X.; Dou, Y. J.; Wang, J.; Xie, L. L.; Lin, F.; Yuan, Y. F. Chem. J. Chin. Univ. 2012, 33, 2244 (in Chinese).
(廖文向, 豆雅洁, 王静, 谢莉莉, 林芬, 袁耀锋, 高等学校化学学报, 2012, 33, 2244.)

[12] Wang, J.; Feng, L. M.; Ma, F. J.; Lin, F.; Xie, L. L.; Yuan, Y. F. Chin. J. Org. Chem. 2012, 32, 1479 (in Chinese).
(王静, 冯丽敏, 马飞娟, 林芬, 谢莉莉, 袁耀锋, 有机化学, 2012, 32, 1479.)

[13] Murray, J. M.; Sweeney, Z. K.; Chan, B. K.; Balazs, M.; Bradley, E.; Castanedo, G.; Chabot, C.; Chantry, D.; Flagella, M.; Goldstein, D. M.; Kondru, R.; Lesnick, J.; Li, J.; Lucas, M. C.; Nonomiya, J.; Pang, J.; Price, S.; Salphati, L.; Safina, B.; Savy, P. P. A.; Seward, E. M.; Ultsch, M.; Sutherlin, D. P. J. Med. Chem. 2012, 55, 7686.

[14] Wang, B.; Liu, C. J.; Wang, J. D.; Lei, Z. K.; Hu, D. L. Chem. J. Chin. Univ. 2012, 33, 76 (in Chinese).
(王斌, 刘晨江, 王吉德, 雷振凯, 胡东林, 高等学校化学学报, 2012, 33, 76.)

[15] Ma, Q. Y.; Guan, R. F.; Li, G. Z., Liu, S. Q.; Zuo, M. Adv. Mater. Res. 2011, 306, 206.

[16] Iyer, E. S. S.; Samanta, D.; Dey, A.; Kundu, A.; Datta, A. J. Phys. Chem. 2012, 116, 1586.

[17] Gogoi, A.; Das, G. Cryst. Growth Des. 2012, 12, 4012.

[18] Cui, L. J.; Xiao, S. Y.; Yang, H. S.; Xu, P.; Cheng, F. S.; Li, Z. H.; Liang, R. H.; Xia, Z. N. Chin. J. Org. Chem. 2011, 31, 674 (in Chinese).
(崔丽君, 肖尚友, 杨昊书, 徐盼, 程凡圣, 李正华, 梁荣辉, 夏之宁, 有机化学, 2011, 31, 674.)

[19] Zhang, Y.; Gao, G. X.; Han, T. T.; Zheng, Y. S. Chem. Propellants Polym. Mater. 2011, 9, 78 (in Chinese).
(张岩, 高国新, 韩婷婷, 郑元锁, 化学推进剂与高分子材料, 2011, 9, 78.) Benito, A.; Martinezmanez, R.; Paya, J.; Soto, J.; Tendero, M. J. L.; Sinn, E. J. Organomet. Chem. 1995, 503, 260.
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