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

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

研究论文

2-单核和双核茂铁基-1,3-二烷基苯并咪唑盐的合成、结构及性质研究

  • 王静 ,
  • 冯丽敏 ,
  • 马飞娟 ,
  • 林芬 ,
  • 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;
    c 福州大学分析测试中心 福州 350108

收稿日期: 2011-12-29

  修回日期: 2012-03-11

  网络出版日期: 2012-04-11

基金资助

福建省自然科学基金(Nos. 2010J01036, 2009J05028)、福建省科技计划重点(No. 2009H0021)资助项目.

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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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摘要

以2-二茂铁基苯并咪唑(2)为原料, 合成了1-甲基-2-二茂铁基-3-乙基苯并咪唑碘盐(4)和六氟磷酸盐(5); 甲酰化的2,2-双二茂铁基丙烷(6)与邻苯二胺在甲醇作溶剂, 回流, 碘催化下反应, 得到2-[1'-(2-二茂铁基丙烷-2-基)二茂铁-1-基]苯并咪唑(7), 以7为原料合成了1-甲基-2-[1'-(2-二茂铁基丙烷-2-基)二茂铁-1-基]-3-乙基苯并咪唑碘盐(9)和六氟磷酸盐(10). 电化学分析表明所得的盐化合物中, 与苯并咪唑阳离子直接相连的二茂铁的氧化电位相对2和7均产生了较大正移. 对化合物4的单晶结构进行了解析, 晶体结构中存在π-π堆积. UV-Vis吸收光谱表明所得盐化合物具有光致电荷迁移现象. DSC-TG(差示扫描量热-热重)测试表明碘盐4对高氯酸铵(AP)热分解有较好催化效果.

关键词： 二茂铁; 双核茂铁基; 苯并咪唑盐

本文引用格式

王静 , 冯丽敏 , 马飞娟 , 林芬 , 谢莉莉 , 袁耀锋 . 2-单核和双核茂铁基-1,3-二烷基苯并咪唑盐的合成、结构及性质研究[J]. 有机化学, 2012 , 32(08) : 1479 -1486 . DOI: 10.6023/cjoc1112291

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

参考文献

[1] (a) Rewcastle, G. W.; Gamage, S. A.; Flanagan, J. U.; Frederick, R.; Denny, W. A.; Baguley, B. C.; Kestell, P.; Singh, R.; Kendall, J. D.; Marshall, E. S.; Lill, C. L.; Lee, W.-J.; Kolekar, S.; Buchanan, C. M.; Jamieson, S. M. F.; Shepherd, P. R. J. Med. Chem. 2011, 54, 7105. (b) Penning, T. D.; Zhu, G.-D.; Gong, J.; Thomas, S.; Gandhi, V. B.; Liu, X.; Shi, Y.; Klinghofer, V.; Johnson, E. F.; Park, C. H.; Fry, E. H.; Donawho, C. K.; Frost, D. J.; Buchanan, F. G.; Bukofzer, G. T.; Rodriguez, L. E.; Bontcheva-Diaz, V.; Bouska, J. J.; Osterling, D. J.; Olson, A. M.; Marsh, K. C.; Luo, Y.; Giranda, V. L. J. Med. Chem. 2010, 53, 3142. (c) Chen, Z. G.; Wang, C. N.; Zhao, P. F.; Wang, Y.; Zhou, L. Y. Acta Chim. Sinica 2010, 68, 2347 (in Chinese). (陈战国, 王传宁, 赵朋飞, 王芸, 周利燕, 化学学报, 2010, 68, 2347.)

[2] Wu, C. L.; Bai, Y. J.; Lv, D. X.; Sun, W.; Shi, Z. Chem. Reag. 2009, 31, 875 (in Chinese). (吴长利, 白银娟, 吕东旭, 孙伟, 史真, 化学试剂, 2009, 31, 875.)

[3] Lee, K. M.; Lee, C. K.; Lin, I. B. Chem. Commun. 1997, 9, 899.

[4] Huynh, H. V.; Holtgrewe, C.; Pape, T.; Koh, L. L.; Hahn, E. Organometallics 2005, 25, 245.

[5] Singh, N.; Jang, D. O. Org. Lett. 2007, 9, 1991.

[6] Li, Y.; Ma, H. Q.; Wang, Y. L. Chin. J. Org. Chem. 2008, 28, 210 (in Chinese). (李焱, 马会强, 王玉炉, 有机化学, 2008, 28, 210.)

[7] Wei, B.; Guo, J; Fu, N. Y.; Yuan, Y. F. Chin. J. Org. Chem. 2008, 28, 791 (in Chinese). (卫兵, 郭建, 傅南雁, 袁耀锋, 有机化学, 2008, 28, 791.)

[8] Wu, K. Q.; Guo, J.; Yan, J.-F.; Xie, L. L.; Xu, F. B.; Bai, S.; Nockemann, P.; Yuan, Y. F. Organometallics 2011, 30, 3504.

[9] Hansen, M. N.; Farjami, E.; Kristiansen, M.; Clima, L.; Pedersen, S. U.; Daasbjerg, K.; Ferapontova, E. E.; Gothelf, K. V. J. Org. Chem. 2010, 75, 2474.

[10] Song, Q. B.; Dong, Y. Chin. J. Org. Chem. 2007, 27, 66 (in Chinese). (宋庆宝, 东宇, 有机化学, 2007, 27, 66.)

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

[12] Snegur, L. V.; Nekrasov, Y. S.; Sergeeva, N. S.; Zhilina, Z. V.; Gumenyuk, V. V.; Starikova, Z. A.; Simenel, A. A.; Morozova, N. B.; Sviridova, I. K.; Babin, V. N. Appl. Organomet. Chem. 2008, 22, 139.

[13] Hamad, M. A.; Ghaleb, M.; Khan, K. M.; Voelter, W. J. Med. Sci. 2008, 673.

[14] AkpInar, H.; Balan, A.; Baran, D.; ünver, E. K.; Toppare, L. Polymer 2010, 51, 6123.

[15] Zapata, F.; Caballero, A.; Tarraga, A.; Molina, P. J. Org. Chem. 2010, 75, 162.

[16] (a) Zhang, J. Z.; Yang, B. Q.; Yang, Y. T.; Zhang, B. L. Chin. J. Appl. Chem. 2007, 24, 1273 (in Chinese). (张俊珍, 杨秉勤, 杨亚婷, 张秉林, 应用化学, 2007, 24, 1273.) (b) Li, X. G.; Yang, B. Q.; Gu, L. J.; Ning, W. Chin. J. Appl. Chem. 2009, 26, 1184 (in Chinese). (李湘广, 杨秉勤, 谷利军, 宁伟, 应用化学, 2009, 26, 1184.)(c) Ma, S. S.; Jiang, S.; Shao, X. X.; Cheng, W.; Yang, B. Q. J. Northwest Univ. (Nat. Sci. Ed.) 2010, 40, 821 (in Chinese). (马珊珊, 姜珊, 邵欣欣, 陈伟, 杨秉勤, 西北大学学报(自然科学版), 2010, 40, 821.)

[17] Wang, L. Y.; Shi, Z. Chem. Bull. 2005, 68, 193 (in Chinese). (王陆瑶, 史真, 化学通报, 2005, 68, 193.)

[18] (a) Yue, K. F.; Zhuo, F.; Hou, L.; Qiang, Y. M.; Zhai, G. H.; Yin, B.; Wang, Y. Y.; Wen, Z. Y. Acta Chim. Sinica 2011, 69, 596 (in Chinese). (岳可芬, 卓飞, 侯磊, 姜严梅, 翟高红, 尹兵, 王尧宇, 文振翼, 化学学报, 2011, 69, 596.) (b) Yue, K. F.; Jiang, Y. M.; Song, Y.; Jiang, F. L.; Huang, X. Y.; Li, T.; Wang, C. J.; Wang, Y. Y. Acta Chim. Sinica 2010, 68, 1291 (in Chinese). (岳可芬, 姜严梅, 宋扬, 姜富灵, 黄小英, 李涛, 王诚军, 王尧宇, 化学学报, 2010, 68, 1291.)

[19] Zhang, J.; Yang, B. Q.; Zhu, H. Y.; Li, T.; Wen, Z. Y. Chin. J. Chem. 2006, 24, 637.

[20] Howarth, J.; Hanlon, K. Tetrahedron Lett. 2001, 42, 751.

[21] Yuan, Y. F.; Zhang, L. Y.; Qian, W. Q.; Wang, J. T.; Liu, W. Y.; Ding, T. Z. Transition Met. Chem. 1997, 23, 21.

[22] Zapata, F.; Caballero, A.; Espinosa, A.; Tarraga, A.; Molina, P. J. Org. Chem. 2009, 74, 4787.

[23] 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, 672 (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, 672.)

[24] Huang, J. X.; Sun, Z.; Hu, Y. C.; Li, Z. Chin. J. Struct. Chem. 1988, 7, 340. (黄锦顺, 孙忠, 胡玉才, 李哲, 结构化学, 1988, 7, 340.)

[25] Stibrany, R. T.; Lobanov, M. V.; Schugar, H. J.; Potenza, J. A. Inorg. Chem. 2004, 43, 1472.

[26] Gao, Y.; Ke, C. F.; Li, H. D.; Xie, L. L.; Yuan, Y. F. Energy Mater. 2011, 19, 19 (in Chinese). (高勇, 柯成锋, 李恒东, 谢莉莉, 袁耀锋, 含能材料, 2011, 19, 19.)
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