Bisurea-Functionalized Macrocycles: Synthesis and Halide Anion-Response

doi:10.6023/cjoc201209006

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (01): 110-115.DOI: 10.6023/cjoc201209006 Previous Articles Next Articles

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含双脲基团大环化合物的合成及其对卤素阴离子检测研究

张读山, 陈金平, 曾毅, 于天君, 李嫕

中国科学院理化技术研究所光化学转换与功能材料重点实验室北京 100190

收稿日期:2012-09-05 修回日期:2012-09-27 发布日期:2012-10-11
通讯作者: 陈金平, 李嫕 E-mail:yili@mail.ipc.ac.cn;chenjp@mail.ipc.ac.cn
基金资助:
国家自然科学基金(Nos. 21233011, 21172229, 21002109, 21103210);国家重点基础研究发展规划(No. 2010CB934500)和北京市科技新星计划资助项目.

Bisurea-Functionalized Macrocycles: Synthesis and Halide Anion-Response

Zhang Dushan, Chen Jinping, Zeng Yi, Yu Tianjun, Li Yi

Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190

Received:2012-09-05 Revised:2012-09-27 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.

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.

Key words: macrocycle, urea, halide anion-responsive, absorption

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Zhang Dushan, Chen Jinping, Zeng Yi, Yu Tianjun, Li Yi. Bisurea-Functionalized Macrocycles: Synthesis and Halide Anion-Response[J]. Chin. J. Org. Chem., 2013, 33(01): 110-115.

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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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含双脲基团大环化合物的合成及其对卤素阴离子检测研究

Bisurea-Functionalized Macrocycles: Synthesis and Halide Anion-Response

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