Articles

Bisurea-Functionalized Macrocycles: Synthesis and Halide Anion-Response

  • Zhang Dushan ,
  • Chen Jinping ,
  • Zeng Yi ,
  • Yu Tianjun ,
  • Li Yi
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  • Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190

Received date: 2012-09-05

  Revised date: 2012-09-27

  Online published: 2012-10-11

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21233011, 21172229, 21002109, 21103210), the National Basic Research Program (No. 2010CB934500) and the Beijing Nova Program.

Abstract

Oxo-bisurea-functionalized macrocycles, cycle 1, cycle 2, and cycle 3, were synthesized by a stepwise coupling approach. Absorption studies reveal that cycle 2 and cycle 3 can bind with halide anions in a 1:1 stoichiometry with binding constants of 105~108 L·mol-1. 1H NMR titration experiments show that urea groups are the binding sites and play important roles in the binding strength.

Cite this article

Zhang Dushan , Chen Jinping , Zeng Yi , Yu Tianjun , Li Yi . Bisurea-Functionalized Macrocycles: Synthesis and Halide Anion-Response[J]. Chinese Journal of Organic Chemistry, 2013 , 33(01) : 110 -115 . DOI: 10.6023/cjoc201209006

References

[1] (a) Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419.

(b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609.

(c) Caltagirone, C.; Gale, P. A. Chem. Soc. Rev. 2009, 38, 520.

[2] (a) Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; Mcree, D. E.; Khazanovich, N. Nature 1993, 366, 324.

(b) Shimizu, L. S.; Hughes, A. D.; Smith, M. D.; Davis, M. J.; Zhang, B. P.; zur Loye, H. C.; Shimizu, K. D. J. Am. Chem. Soc. 2003, 125, 14972.

(c) Shimizu, L. S.; Smith, M. D.; Hughes, A. D.; Shimizu, K. D. Chem. Commun. 2001, 1592.

[3] (a) Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844.

(b) Lankshear, M. D.; Beer, P. D. Acc. Chem. Res. 2007, 40, 657.

[4] (a) Custelcean, R.; Remy, P.; Bonnesen, P. V.; Jiang, D. E.; Moyer, B. A. Angew. Chem., Int. Ed. 2008, 47, 1866.

(b) dos Santos, C. L. M. G.; McCabe, T.; Watson, G. W.; Kruger, P. E.; Gunnlaugsson, T. J. Org. Chem. 2008, 73, 9235.

(c) Perez-Casas, C.; Yatsimirsky, A. K. J. Org. Chem. 2008, 73, 2275.

(d) Boiocchi, M.; Del Boca, L.; Gómez, D. E.; Fabbrizzi, L.; Licchelli, M.; Monzani, E. J. Am. Chem. Soc. 2004, 126, 16507.

(e) Hay, B. P.; Firman, T. K.; Moyer, B. A. J. Am. Chem. Soc. 2005, 127, 1810.

(f) Lee, D. H.; Lee, K. H.; Hong, J. I. Org. Lett. 2001, 3, 5.

[5] (a) Ranganathan, D. Acc. Chem. Res. 2001, 34, 919.

(b) Brooks, S. L.; Garcia-Garrido, S. E.; Light, M. E.; Cole, P. A.; Gale, P. A. Chem. Eur. J. 2007, 13, 3320.

[6] (a) Snellink-Ruel, B. H. M.; Antonisse, M. M. G.; Engbersen, J. F. J.; Timmerman, P.; Reinhoudt, D. N. Eur. J. Org. Chem. 2000, 165.

(b) Meshcheryakov, D.; Bohmer, V.; Bolte, M.; Hubscher-Bruder, V.; Arnaud-Neu, F. Chem. Eur. J. 2009, 15, 4811.

(c) Ranganathan, D.; Lakshmi, C.; Karle, I. L. J. Am. Chem. Soc. 1999, 121, 6103.

[7] (a) Mooibroek, T. J.; Gamez, P. Inorg. Chim. Acta 2007, 360, 381.

(b) Lowik, D. W. P. M.; Lowe, C. R. Eur. J. Org. Chem. 2001, 2825.

(c) Yang, X. P.; Lowe, C. R. Tetrahedron Lett. 2003, 44, 1359.

(d) Wang, M. X.; Yang, H. B. J. Am. Chem. Soc. 2004, 126, 15412.

(e) Wang, D. X.; Zheng, Q. Y.; Wang, Q. Q.; Wang, M. X. Angew. Chem., Int. Ed. 2008, 47, 7485.

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