Investigation of Self-assembled Inclusion Complexes of Cucurbit[n=5～8]urils with Polyamines Guests

Acta Chimica Sinica ›› 2004, Vol. 62 ›› Issue (24): 2431-2440. Previous Articles Next Articles

瓜环与链状客体自组装包结配合物结构模式的考察

戴丽萍¹, 陶朱¹, 祝黔江¹, 薛赛凤¹, 张建新², 周欣²

1. 贵州大学应用化学研究所, 贵阳, 550025;
2. 贵州省天然产物重点化学实验室, 贵阳, 550002

投稿日期:2004-03-03 修回日期:2004-07-15 发布日期:2014-02-17
通讯作者: 陶朱,E-mail:gzutao@263.net E-mail:gzutao@263.net
基金资助:
国家自然科学基金(Nos.200261002,20362003)、科技部国际科技合作重点计划(No.2003DF000030)、贵州省省长基金、贵州省重点基金(No.2003004)、贵州省教育厅自然科学研究基金资助项目.

Investigation of Self-assembled Inclusion Complexes of Cucurbit[n=5～8]urils with Polyamines Guests

DAI Li-Ping¹, TAO Zhu¹, ZHU Qian-Jiang¹, XUE Sai-Feng¹, ZHANG Jian-Xin², ZHOU Xin²

1. Institute of Applied Chemistry, Guizhou University, Guiyang 550025;
2. Key Laboratory of Chemistry for Natural Products of Guizhou Province, Guiyang 550002

Received:2004-03-03 Revised:2004-07-15 Published:2014-02-17

Abstract

A series of N,N'-bis(pyridylmethyl)-diaminoalkanes have been synthesized from 2,3 or 4-pyridinecarboxaldehyde and different diamines. The possibility of self-assembly psedorotaxanes of cucurbit[n=5～8]urils with rod materials has been investigated by using NMR techniques. Here the rod materials or guests are polyamines of N,N'-bis(pyridylmethyl)-diaminoalkane. The structures of the host-guest complexes of the cucurbit[n=5～8]urils with the rods were discussed in details. The experimental rsults revealed that different interaction models could be formed from different cucurbit[n=5～8]urils and different N,N'-bis(pyridylmethyl)-diaminoalkanes, also multiple interaction models could be formed from a certain cucurbit[n]uril and a certain N,N'-bis(pyridylmethyl)-diaminoalkane. These suggestions for the interaction models were supported by the ESMS spectroscopy.

Key words: NMR technique, ESMS mass spectra, cucurbit[n]uril, polyamine, host-guest complex

Cite this article

DAI Li-Ping, TAO Zhu, ZHU Qian-Jiang, XUE Sai-Feng, ZHANG Jian-Xin, ZHOU Xin. Investigation of Self-assembled Inclusion Complexes of Cucurbit[n=5～8]urils with Polyamines Guests[J]. Acta Chimica Sinica, 2004, 62(24): 2431-2440.

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[1] Freeman, W. A.; Mock, W. L. J. Am. Chem. Soc. 1981, 103(24), 7367.
[2] Freeman, W. A. Acta Crystallogr. Sect B: Struct. Sci. 1984, B40(4), 382.
[3] Mock, W. L.; Shih, N. Y. J. Org. Chem. 1986, 51(23), 4440.
[4] Buschmann, H. J.; Cleve, E.; Schollmeyer, E. Inog. Chim. Acta 1992, 193(1), 93.
[5] Hoffmann, R.; Knoche, W.; Fenn, C.; Buschmann, H. J. J. Chem. Soc., Faraday Trans. 1994, 90(11), 1507.
[6] Kim, K. Chem. Soc. Rev. 2002, 31(2), 96.
[7] Lim, Y. B.; Kim, T.; Lee, J. W.; Kim, S.; Kim, H. J.; Kim, K.; Park, J. S. Bioconjugate Chem. 2002, 13(6), 1181.
[8] Day, A. I.; Arnold, A. P. WO 0068232, 2000, 8.
[9] Kim, J.; Jung, I. S.; Kim, S. Y.; Lee, E.; Kang, J. K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122(3), 540.
[10] Day, A. I.; Blanch, R. J.; Arnold, A. P.; Lorenzo, S.; Lewis, G. R.; Dance, I. Angew. Chem., Int. Ed. 2002, 41(2), 275.
[11] Ong, W.; Kaifer, A. E. Angew. Chem., Int. Ed. 2003, 42(19), 2164.
[12] Day, A. I.; Arnold, A. P.; Blanch, R. J.; Snushall, B. J. Org. Chem. 2001, 66(24), 8094.
[13] Lorenzo, S.; Day, A. I.; Craig, D. Cryst. Eng. Commun. 2001, 49, 1.
[14] Ong, W.; Gomez-Kaifer, M.; Kaifer, A. E. Org. Lett. 2002, 4(10), 1791.
[15] Shen, Y.-Q.; Xue, S.-F.; Zhao, Y.-J.; Zhu, Q.-J.; Tao, Z. Chin. Sci. Bull. 2003, 48(11), 2333 (in Chinese).(申永强, 薛赛凤, 赵云洁, 祝黔江, 陶朱, 科学通报, 2003, 48(11), 2333.)
[16] Liu, J.-X.; Tao, Z.; Xue, S.-F.; Zhu, Q.-J.; Zhang, J.-X. Chin. J. Inorg. Chem. 2004, 20(2), 139 (in Chinese).(刘静欣, 陶朱, 薛赛凤, 祝黔江, 张建新, 无机化学学报, 2004, 20(2), 139.)
[17] Fu, H.-Y.; Xue, S.-F.; Tao, Z.; Zhang, J.-X.; Day, A. I. J. Incl. Phenom. Macrocycl. Chem. Accepted.
[18] Jon, S. Y.; Selvapalam, N.; Oh, D. H.; Kang, J. K.; Kim, S. Y.; Jeon, Y. J.; Lee, J. W.; Kim, K. J. Am. Chem. Soc. 2003, 125(34), 10186.
[19] Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H. J.; Kim, K. Acc. Chem. Res. 2003, 36(8), 621.
[20] Christopher, A.; Witt, D.; Fettinger, J. C.; Isaacs, L. J. Org. Chem. 2003, 68(16), 6184.
[21] Zhang, G.-L.; Xu, Z.-Q.; Xue, S.-F.; Zhu, Q.-J.; Tao, Z. Chin. J. Inorg. Chem. 2003, 19(6), 655 (in Chinese).(张桂玲, 徐周庆, 薛赛凤, 祝黔江, 陶朱, 无机化学学报, 2003, 19(6), 655.)
[22] Zhao, J.-Z.; Kim, H. J.; Oh, J.; Kim, S. Y.; Lee, J. W.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40(22), 4233.
[23] Isobe, H.; Sato, S.; Nakamura, E. Org. Lett. 2002, 4(8), 1287.
[24] Shen, Y.-Q. M.S. Thesis, Guizhou University, Guiyang, 2003.(申永强, 硕士论文, 贵州大学, 贵阳, 2003.)
[25] Day, A. I.; Arnold, A. P.; Blanch, R. J. Molecules 2003, 8(1), 74.
[26] Zhao, Y.-J.; Shen, Y.-Q.; Xue, S.-F.; Zhu, Q.-J.; Tao, Z.; Zhang, J.-X.; Wei, Z.-B.; Long, L.-S.; Day, A. I. Chin. Sci. Bull. 2004, 49(11), 1111.
[27] Luo, X.-Q.; Xue, S.-F.; Zhu, Q.-J.; Tao, Z. J. Guizhou Univ. Nat. Sci. Ed. 2001, 18(1), 184 (in Chinese). (罗绪强, 薛赛凤, 祝黔江, 陶朱, 贵州大学学报(自然科学版), 2001, 18(1), 184.)
[28] Dai, L.-P.; Zhang, G.-Y.; Yao, X.-Q.; Xue, S.-F.; Zhu, Q.-J.; Tao, Z. J. Guizhou Univ. Nat. Sci. Ed. 2003, 20(2), 157 (in Chinese).(戴丽萍, 张广义, 姚晓青, 薛赛凤, 祝黔江, 陶朱, 贵州大学学报(自然科学版), 2003, 20(2), 157.)
[29] Xu, Z.-Q.; Yao, X.-Q.; Xue, S.-F.; Zhu, Q.-J.; Tao, Z.; Zhang, J.-X.; Wei, Z.-B.; Long, L.-S. Acta Chim. Sinica 2004, 62, 1927 (in Chinese).(徐周庆, 姚晓青, 薛赛凤, 祝黔江, 陶朱, 张建新, 魏赞斌, 龙腊生, 化学学报, 2004, 62, 1927.)

瓜环与链状客体自组装包结配合物结构模式的考察

Investigation of Self-assembled Inclusion Complexes of Cucurbit[n=5～8]urils with Polyamines Guests

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