Chinese Journal of Organic Chemistry >
Synthesis of Hollow Aromatic Helix and Their Selective Recognition for Alkali Metal Ions
Received date: 2016-01-04
Revised date: 2016-05-09
Online published: 2016-05-17
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21274051, 21574054).
A novel type of hollow aromatic helices was prepared according to an improved organic synthesis approach. By means of UV-Vis spectroscopy, the recognition and selectivity of aromatic helix (AH) for alkali metal ions were investigated. The results indicated that AH could specifically recognize the alkali metal ions with an order of Rb+ > K+ > Cs+ > Na+ > Li+. In addition, the fluorescence titration was carried out by adding Rb+ into the AH solution, which further underpinned the binding capacity and sensitive responsiveness of AH for the alkali metal ions.
Key words： aromatic helix; hollow channel; alkali metal ions; selective recognition
Li Wenfang , Zhu Junyan , Dong Zeyuan . Synthesis of Hollow Aromatic Helix and Their Selective Recognition for Alkali Metal Ions[J]. Chinese Journal of Organic Chemistry, 2016 , 36(7) : 1668 -1671 . DOI: 10.6023/cjoc201601004
[1] Hille, B. Ionic Channels of Excitable Membranes, 3rd ed., Sinauer Associates: Sunderland, MA, 2001.
[2] Tabushi, I.; Kuroda, Y.; Yokota, K. Tetrahedron Lett. 1982, 23(44), 4601.
[3] Cornell, B. A.; Braach-Maksvytis, V.; King, L.; Osman, P.; Raguse, B.; Wieczorek, L.; Pace, R. Nature 1997, 387(6633), 580.
[4] Das, G.; Talukdar, P.; Matile, S. Science 2002, 298(5598), 1600.
[5] Sakai, N.; Matile, S. Langmuir 2013, 29, 9031.
[6] Zhang, D.; Yang, Z.Y. J. Phys. Chem. B 2011, 115(49), 4333.
[7] Blake, A. J.; Cooke, P. A.; Doyle, K. J.; Gair, S.; Simpkins, N. S. Tetrahedron Lett. 1998, 39, 9093.
[8] Goto, H.; Katagiri, H.; Furusho, Y.; Yashima, E. J. Am. Chem. Soc. 2006, 128,7176.
[9] Nakano, T.; Okamoto ,Y. Chem. Rev. 2001, 101, 4013.
[10] de Witte, P. A. J.; Castriciano, M.; Cornelissen, J.J. L. M.; Scolaro, L. M.; Nolte, R. J. M.; Rowan, A. E. Chem. Eur. J. 2003, 9, 1775.
[11] Delsuc, N; Godde, F.; Kauffmann, B.; Léger, J. M.; Huc, I. J. Am. Chem. Soc. 2007, 129, 11348.
[12] Kudo, M.; Maurizot, V.; Kauffmann, B.; Tanatani, A.; Huc, I. J. Am. Chem. Soc. 2013, 135, 9628.
[13] Chandramouli, N.; Ferrand, Y.; Lautrette, G.; Kauffmann, B.; Mackereth, C. D.; Laguerre, M.; Dubreuil, D.; Huc, I. Nat. Chem. 2015, 7, 334.
[14] Zhu, J. Y.; Dong, Z. Y.; Lei, S. B.; Cao, L. L.; Yang, B.; Li, W. F.; Zhang , Y. C.; Liu, J. Q. ; Shen, J. C. Angew. Chem., Int. Ed. 2015, 54, 3097.
[15] Ren, C. L.; Victor, M.; Zhao, H. Q.; Shen, J.; Zhou, F.; Ong, W. Q.; Du, Z. Y.; Zhang, K.; Su, H. B.; Zeng, H. Q. J. Am. Chem. Soc. 2011, 133, 13930.
[16] Zhang, Z. M.; Qiu, F. Z. World Chin. J. Digestol. 2005, 13(5), 585 (in Chinese). (张宗明, 裘法祖, 世界华人消化杂志, 2005, 13(5), 585.)
[17] Berni, E.; Kauffmann, B.; Bao, C. Y.; Lefeuvre, J.; Bassani, D. M.; Huc, I. Chem. Eur. J. 2007, 13, 8463.
[18] Ren, X. F.; Xu, J. L.; Chen, S. H. Chin. J. Org. Chem. 2006, 26, 454 (in Chinese). (任新锋, 徐菁利, 陈思浩, 有机化学, 2006, 26, 454.)
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