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

doi:10.6023/cjoc201301036

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

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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

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 Hongmin^a,b, Wang Wei^a,b, Zhu Xiaoxiao^a,b, Chen Weiqiang^a,b, Xie Lili^a,b, Yuan Yaofeng^a,b

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 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

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Ye Hongmin, Wang Wei, Zhu Xiaoxiao, Chen Weiqiang, Xie Lili, Yuan Yaofeng. Synthesis Crystal Structure and Properties of Iodide, Hexafluoro- phosphate and Bis(trifluoromethane sulfonamide) Salts of 1-Ferrocenyl Methyl-2-ferrocenyl-3-alklybenzimidazolium[J]. Chin. J. Org. Chem., 2013, 33(04): 827-834.

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References

[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.

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

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

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