SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 08: 1804 - 1809

DOI: https://doi.org/10.6023/cjoc201302008

Articles

1,3-Disubstituted p-tert-Butylcalix[4]arene Derivatives Bearing Phenanthroline Moieties：Synthesis and Selective Recognition of Silver Ion

  • Li Liang ,
  • Qi Weiguang ,
  • Wang Chao ,
  • Yan Chaoguo
Expand
  • a School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418;
    b College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002

Received date: 2013-02-04

  Revised date: 2013-03-04

  Online published: 2013-03-28

Supported by

Project supported by the National Natural Science Foundation of China (No. 20972132).

Fold

Abstract

p-tert-Butylcalix[4]arene-1,3-dialdehydes were firstly obtained by two step alkylations of p-tert-butylcalix[4]arene with alkylene dihalide and hydroxyl-substituted benzaldehydes. Then p-tert-butylcalix[n]arene 1,3-disubstituted phenanthrolines were successfully prepared by condensation of active calixarene dialdehydes with 1,10-phenanthroline-5,6-dione. The structures of the prepared hoters were characterized with IR, NMR, and HRMS techniques. The recogination of calixarene 1,3-disubstituted phenanthroline for metal ions was studied with UV-Vis spectroscopy. A great affinity for Ag+ ions that can be clearly detected by naked eye was obtained.

Key words： calixarene; phenanthroline; UV spectroscopy; ion recognition

Cite this article

Li Liang , Qi Weiguang , Wang Chao , Yan Chaoguo . 1,3-Disubstituted p-tert-Butylcalix[4]arene Derivatives Bearing Phenanthroline Moieties：Synthesis and Selective Recognition of Silver Ion[J]. Chinese Journal of Organic Chemistry, 2013 , 33(08) : 1804 -1809 . DOI: 10.6023/cjoc201302008

References

[1] Biros, S. M.; Rebek, J. Jr. Chem. Soc. Rev. 2007, 36, 93.
[2] Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780.
[3] Liu, Y.; You, C. C.; Zhang, H. Y. Supramolecular Chemistry Molecular Recogimation and Assembly of Synthetic Accepter, Nankai University Press, Tianjin, 2001 (in Chinese).
(刘育, 尤长城, 张衡益 超分子化学——合成受体的分子识别与组装, 南开大学出版社, 天津, 2001.)
[4] Zhao, B.-T.; Zhang, H.-Y.; Liu, Y. Chin. J. Org. Chem. 2005, 25(8), 913 (in Chinese).
(赵邦屯, 张衡益, 刘育, 有机化学, 2005, 25(8), 913.)
[5] Guo, D.-S.; Liu, Y. Chem. Soc. Rev. 2012, 41, 5907.
[6] Dondoni, A.; Marra, A. Chem. Rev. 2010, 110(9), 4949.
[7] Joseph, R.; Rao C. P. Chem. Rev. 2011, 111(8), 4658.
[8] Rillema, D. P.; Cruz, A. J.; Moore, C.; Siam, K.; Jehan, A.; Base, D.; Nguyen, T.; Huang, W. Inorg. Chem. 2013, 52(2), 596.
[9] Lazorski, M. S.; Gest, R. H.; Elliott, C. M. J. Am. Chem. Soc. 2012, 134(50), 20566.
[10] Lazorski, M. S.; Gest, R. H.; Elliott, C. M. J. Am. Chem. Soc. 2012, 134(42), 17466.
[11] Batista, R. M. F.; Costa, S. P. G.; Belsley, M.; Lodeiro, C.; Raposo, M. Tetrahedron 2008, 64, 9230.
[12] Ammaxm, M.; Bauerle, P. Org. Biomol. Chem. 2005, 3, 4143.
[13] Lam, F.; Chan, K. S.; Liu, B.-J. Tetrahedron Lett. 1995, 36, 6261.
[14] Larn, F.; Feng, M.; Chan, K. S. Tetrahedron 1999, 55, 8377.
[15] Li, G.-K.; Xu, Z.-X.; Chen, C.-F.; Huang, Z.-T. Chem. Commun. 2008, 1774.
[16] Chen, Q.-Y.; Chen, C.-F. Tetrahedron Lett. 2005, 46, 165.
[17] Li, L.; Gu, W.; Yan, C.-G. Chin. J. Chem. 2009, 27, 1975.
[18] Li, L.; Gu, W.-W., Yan, C.-G. Chem. Res. Chin. Univ. 2010, 26, 38.
[19] Lenaerts, P.; Storms, A.; Mullens, J.; D'Haen, J.; Gorller-Walrand, C.; Binnemans, K.; Driesen, K. Chem. Mater. 2005, 17, 5194.
[20] Sun, J.; Liu, D. M.; Yan, C. G. J. Coord. Chem. 2009, 2337.
[21] Liu, Z.; Zhang, S.; Wang, Z. L.; Xia, G. M.; Gao, Y. Chin. J Org. Chem. 2010, 30, 1672 (in Chinese).
(刘志莲, 张书香, 王志玲, 夏光明, 高云华, 有机化学, 2010, 30, 1672.)
Options
Outlines

/

〈 〉