Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles

doi:10.6023/cjoc201910022

Abstract

The promotion of two sulfate or carboxylate-bearing acyclic cucurbiturils for the water-solubility of arenes and aromatic aldehydes is described. ¹H NMR experiments reveals that sulfate-bearing acyclic cucurbituril (acCB-1) signficantly improves the water-solubility of a number of arenes and aldehydes. For 4,4'-dimethylbiphenyl and biphenyl-4,4'-dicarbaldehyde, the solubility can be improved to 8.9 and 11.2 mmol/L, respectively. ¹⁹F NMR experiments demonstrate that carboxylate-bearing acyclic cucurbituril can increase the water-solubilities of pentafluorotoluene and hexafluorobenzene to 5.6 and 3.0 mmol/L, respectively. It is also found that the water-solubilization of acCB-1 for aromatic aldehydes can promote their reaction with acylhydrazines to form hydrozone derivatives. By making use of this promotion, two hydrazone-based macrocycles can be formed from the coupling reactions of two aromatic dialdehdes and one diacylhydrazine in water.

Key words: acyclic cucurbituril, water-solubilization, encapsulation, arene, aromatic aldehyde, hydrazine, macrocycle

Cite this article

Liu Xu-Bo, Lin Jia-Le, Wang Hui, Zhang Dan-Wei, Li Zhan-Ting. Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 663-668.

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References

[1] (a) Birch, H.; Redman, A. D.; Letinski, D. J.; Lyon, D. Y.；Mayer, P. Anal. Chim. Acta 2019, 1086, 16.
(b) Li, H.; Jia, X.; Li, Y.; Shi, X.; Hao, J. J. Phys. Chem. B 2006, 110, 68.
(c) Chen, Y.; Huang, F.; Li, Z.-T.; Liu, Y. Sci. China Chem. 2018, 61, 979.
(d) Yang, Z.; Peng, Y.; Qiu, L. Chin. Chem. Lett. 2018, 29, 1839.
(e) Wang, K.; Guo, D.-S.; Liu, Y. Chem.-Eur. J. 2012, 18, 8758.
(f) Wang, K.; Guo, D.-S.; Liu, Y. Chem.-Eur. J. 2010, 16, 8006.
[2] (a) Liu, R.; Zhang, Y.; Wu, W.; Liang, W.; Huang, Q.; Yu, X.; Xu, W.; Zhou, D.; Selvapalam, N.; Yang, C. Chin. Chem. Lett. 2019, 30, 577.
(b) Zhang, L.; Zhang, Y.-M.; Liu, G.; Liu, Y. Chin. Chem. Lett. 2019, 30, 120.
(c) Zhang, Y.-M.; Xu, Q.-Y.; Liu, Y. Sci. China Chem. 2019, 62, 549.
(d) Xu, C.; Xu, L.; Ma, X. Chin. Chem. Lett. 2018, 29, 970.
(e) Zhao, Q.; Chen, Y.; Liu, Y. Chin. Chem. Lett. 2018, 29, 84.
(f) Song, S.; Li, M.; Gong, X.; Han, H.; Zhou, Y.; Wang, L.; Shuang, S.; Dong, C. Chem. Res. Chin. Univ. 2018, 34, 203.
(g) Zhang, Y.; Chen, Y.; Li, J.; Liang, L.; Liu, Y. Acta Chim. Sinica 2018, 76, 622(in Chinese). (张依, 陈湧, 李晶晶, 梁璐, 刘育, 化学学报, 2018, 76, 622.)
(h) Wang, R.; Wei, Z.; Guo, J.; Feng, Y.; Xu, E.; Duan, H.; Lin, Y.; Yang, Q.; Du, J.; Li, Y. Chem. Res. Chin. Univ. 2018, 34, 180.
(i) Chen, X.-M.; Chen, Y.; Liu, Y. Chin. J. Chem. 2018, 36, 526.
(j) Liu, A.; Xiong, C.; Ma, X.; Ma, W.; Sun, R. Chin. J. Chem. 2019, 37, 793.
(k) Song, C.; Xiao, Y.; Li, K.; Zhang, X.; Lu, Y. Chin. Chem. Lett. 2019, 30, 1249.
(l) Fang, X.; Yan, D. Sci. China Chem. 2018, 61, 397.
[3] (a) Loftsson, T.; Brewster, M. E. J. Pharm. Sci. 1996, 85, 1017.
(b) Uekaji, Y.; Terao, K. J. Inclusion Phenom. Macrocyclic Chem.. 2019, 93, 3.
(c) Shao, W.; Liu, X.; Wang, T.; Hu, X. Chin. J. Org. Chem. 2018, 38, 1107(in Chinese). (邵为, 刘昕, 王婷婷, 胡晓玉, 有机化学, 2018, 38, 1107.)
(d) Li, J.; Pan, D.; Yi, J.; Hao, L.; Kang, Q.; Liu, X.; Lu, L.; Lu, J. Carbohydr. Polym. 2019, 223, 115115.
(e) Liu, G.; Yuan, Q.; Hollett, G.; Zhao, W.; Kang, Y.; Wu, J. Polym. Chem. 2018, 9, 3436.
(f) Bian, X.; Zhao, B.; Pang, B.; Zheng, Z.; Liu, S.; Liu, Z.; Song, F. Chin. J. Chem. 2019, 37, 581.
(g) Yang, Z.; Peng, Y.; Qiu, L. Chin. Chem. Lett. 2018, 29, 1839.
(h) Liang, L.; Chen, Y.; Chen, X.-M.; Zhang, Y.; Liu, Y. Chin. Chem. Lett. 2018, 29, 989.
(i) Wang, X.; Yang, Y.; Fan, L.; Yang, F.; Wu, D. Sci. China Chem. 2018, 61, 311.
[4] (a) Ma, Y.; Xue, M.; Zhang, Z.; Chi, X.; Huang, F. Tetrahedron 2013, 69, 4532.
(b) Li, Z.; Hou, N.; Shao, W.; Xiao, S.; Lin, C.; Wang, L. Chin. J. Org. Chem. 2018, 38, 2002(in Chinese). (李臻益, 候娜娜, 邵为, 肖守军, 林晨, 王乐勇, 有机化学, 2018, 38, 2002.)
(c) Shu, X.; Xu, K.; Hou, D.; Li, C. Isr. J. Chem. 2018, 58, 1194.
(d) Li, Z.; Yang, J.; Huang, F. Chin. J. Chem. 2018, 36, 59.
(e) Yang, X.; Mao, W.; Liu, Y.; Li, L.; Ma, D. Chin. J. Chem. 2019, 37, 575.
[5] (a) Mock, W. L. Top. Curr. Chem. 1995, 175, 1.
(b) Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844.
(c) Yang, X.; Liu, F.; Zhao, Z.; Liang, F.; Zhang, H.; Liu, S. Chin. Chem. Lett. 2018, 29, 1560.
(d) Jiao, Y.; Zhang, X. Acta Chim. Sinica 2018, 76, 659(in Chinese). (焦阳, 张希, 化学学报, 2018, 76, 659.)
(e) Wang, H.; Kan, J.; Bian, B.; Chen, Q.; Tao, Z.; Xiao, X. Chin. J. Org. Chem. 2018, 38, 3094(in Chinese). (王海燕, 阚京兰, 边炳, 陈青, 陶朱, 肖昕, 有机化学, 2018, 38, 3094.)
(f) Yu, S.-B.; Qi, Q.; Yang, B.; Wang, H.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Small 2018, 14, 1801037.
(g) Li, X.-F.; Yu, S.-B.; Yang, B.; Tian, J.; Wang, H.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Sci. China Chem. 2018, 61, 830.
(h) Zhang, B.; Dong, Y.; Li, J.; Yu, Y.; Li, C.; Cao, L. Chin. J. Chem. 2019, 37, 269.
(i) Bai, D.; Zhou, Y.; Lu, J.; Liu, Q.; Chen, Q.; Tao, Z.; Xiao, X. Chin. J. Org. Chem. 2018, 38, 1477(in Chinese). (白东, 周杨, 卢季红, 刘青云, 陈青, 陶朱, 肖昕, 有机化学, 2018, 38, 1477.)
(j) Xu, H.; Wang, Q. Chin. Chem. Lett. 2019, 30, 337.
(k) Wu, W.; Song, S.; Cui, X.; Sun, T.; Zhang, J.-X.; Ni, X.-L. Chin. Chem. Lett. 2018, 29, 95.
(l) Wu, Y.-P.; Yan, M.; Gao, Z.-Z; Hou, J.-L.; Wang, H.; Zhang, D.-W.; Zhang, J.; Li, Z.-T. Chin. Chem. Lett. 2019, 30, 1383.
(m) Yan, M.; Liu, X.-B.; Gao, Z.-Z.; Wu, Y.-P.; Hou, J.-L.; Wang, H.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Org. Chem. Front. 2019, 6, 1698.
(n) Wu, Y.-P.; Wang, Z.-K.; Wang, H.; Zhang, D.-W.; Zhao, X.; Li, Z.-T. Acta Chim. Sinica 2019, 77, 735(in Chinese). (吴义鹏, 王泽坤, 王辉, 张丹维, 赵新, 黎占亭, 化学学报, 2019, 77, 735.)
(o) Li, T.-T.; Wen, L.-L.; Ji, H.-L.; Liu, F.-Y.; Sun, S.-G. Chin. Chem. Lett. 2017, 28, 463.
[6] (a) Huang, J.; Xu, Z.; Lian, X.; Zhang, X.; Tao, Z.; Zhou, Q.; Zhang, Q.; Wei, G. Chem. J. Chin. Univ. 2018, 39, 2425(in Chinese). (黄净净, 许志玲, 练小卫, 张晓东, 陶朱, 周清娣, 张前军, 卫钢, 高等学校化学学报, 2018, 39, 2425.)
(b) Lian, X.; Huang, J.; Tao, Z.; Zhou, Q.; Zhang, Q.; Wei, G. Chem. J. Chin. Univ. 2018, 39, 226(in Chinese). (练小卫, 黄净净, 陶朱, 周清娣, 张前军, 卫钢, 高等学校化学学报, 2018, 39, 226.)
(c) Li, S.; Chan, J. Y.-W.; Li, Y.; Bardelang, D.; Zheng, J.; Yew, W. W.; Chan, D. P.-C.; Lee, S. M. Y.; Wang, R. Org. Biomol. Chem. 2016, 14, 7563.
(d) Chu, J. J.; Apps, M. G.; Wheate, N. J. Supramol. Chem. 2014, 26, 648.
(e) Ma, W.-J.; Chen, J.-M.; Jiang, L.; Yao, J.; Lu, T.-B. Mol. Pharm. 2013, 10, 4698.
(f) Huang, Y.; Xue, S.-F.; Tao, Z.; Zhu, Q.-J.; Zhang, H.; Lin, J.-X.; Yu, D.-H. J. Inclusion Phenom. Macrocyclic Chem. 2008, 61, 171.
(g) Zhao, Y.; Buck, D. P.; Morris, D. L.; Pourgholami, M. H.; Day, A. I.; Collins, J. G. Org. Biomol. Chem. 2008, 6, 4509.
(h) Yang, B.; Zhang, X.-D.; Li, J.; Tian, J.; Wu, Y.-P.; Yu, F.-X.; Wang, R.; Wang, H.; Zhang, D.-W.; Liu, Y.; Zhou, L.; Li, Z.-T. CCS Chem. 2019, 1, 156.
(i) Zhang, Z.; Kan, J.; Feng, H.; Liu, Q.; Tao, Z.; Xiao, X. Chin. J. Org. Chem. 2018, 38, 1972(in Chinese). (张智睿, 阚京兰, 冯华明, 刘青云, 陶朱, 肖昕, 有机化学, 2018, 38, 1972.)
(j) Zhang, T.; Liu, Y.; Hu, B.; Zhang, C.; Chen, Y.; Liu, Y. Chin. Chem. Lett. 2019, 30, 949.
(k) Yi, J.; Song, S.; Zhang, S.; Zhang, S.; Tian, M.; Ni, X. Chem. J. Chin. Univ. 2018, 39, 911(in Chinese). (易君明, 宋森, 张胜, 张少威, 田蒙奎, 倪新龙, 高等学校化学学报, 2018, 39, 911.)
(l) Bai, D.; Wang, X.; Gao, Z.; Qiu, S.; Tao, Z.; Zhang, J.; Xiao, X. Chin. J. Org. Chem. 2017, 37, 2022(in Chinese). (白东, 王鑫, 高中政, 邱胜超, 陶朱, 张建新, 肖昕, 有机化学, 2017, 37, 2022.)
(m) Yin, Z.-J.; Wu, Z.-Q.; Lin, F.; Qi, Q.-Y.; Xu, X.-N.; Zhao, X. Chin. Chem. Lett. 2017, 28, 1167.
(n) Gao, Z.; Yang, L.; Bai, D.; Chen, L.; Tao, Z.; Xiao, X. Chem. J. Chin. Univ. 2017, 38, 212(in Chinese). (高中政, 杨立国, 白东, 陈丽霞, 陶朱, 肖昕, 高等学校化学学报, 2017, 38, 212.)
[7] Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Acc. Chem. Res. 2003, 36, 621.
[8] (a) Ma, D.; Zavalij, P. Y.; Isaacs, L. J. Org. Chem. 2010, 75, 4786.
(b) Ma, D.; Glassenberg, R.; Ghosh, S.; Zavalij, P. Y.; Isaacs, L. Supramol. Chem. 2012, 24, 325.
(c) Zhang, M.; Sigwalt, D.; Isaacs, L. Chem. Commun. 2015, 51, 14620.
[9] (a) Ma, D.; Hettiarachchi, G.; Nguyen, D.; Zhang, B.; Wittenberg, J. B.; Zavalij, P. Y.; Briken, V.; Isaacs, L. Nat. Chem. 2012, 4, 503.
(b) Zhang, B.; Zavalij, P. Y.; Isaacs, L. Org. Biomol. Chem. 2014, 12, 2413.
[10] (a) Mao, D.; Liang, Y.; Liu, Y.; Zhou, X.; Ma, J.; Jiang, B.; Liu, J.; Ma, D. Angew. Chem., Int. Ed. 2017, 56, 12614.
(b) Mao, W.; Mao, D.; Yang, F.; Ma, D. Chem.-Eur. J. 2019, 25, 2272.
[11] Choi, H.; Ahn, J.; Kim, S.; Kim, H.; Jung, J. H. Chem. Commun. 2016, 52, 7600.
[12] Kotha, S.; Shah, V. R. Synthesis 2007, 3653.
[13] Zha, D.; You, L. ACS Appl. Mater. Interfaces 2016, 8, 2399.
[14] Zhang, D.; Li, Z. Chin. J. Org. Chem. 2012, 32, 2009(in Chinese). (张丹维, 黎占亭, 有机化学, 2012, 32, 2009.)
[15] Wei, X.; Gu, J.; Liu, X.; Huang, C.; Zhu, B. Chin. J. Org. Chem. 2018, 38, 3386(in Chinese). (魏小康, 谷静池, 刘兴丽, 黄超, 朱必学, 有机化学, 2018, 38, 3386.)

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