Study on the Effect of Host-Guest Based on the Dimethoxy-pillar[5]arene and Benzazole Heterocyclic Compounds

doi:10.6023/cjoc201712037

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1718-1724.DOI: 10.6023/cjoc201712037 Previous Articles Next Articles

Special Issue: 有机超分子化学合辑

Articles

甲氧基柱[5]芳烃对苯并唑类杂环化合物的主客体作用研究

师海雄^a,b, 程晓斌^a, 林奇^a, 姚虹^a, 张有明^a, 魏太保^a

a 西北师范大学化学化工学院教育部生态环境相关材料重点实验室甘肃省高分子材料重点实验室兰州 730070;
b 兰州文理学院化工学院兰州 730000

收稿日期:2017-12-26 修回日期:2018-03-14 发布日期:2018-03-29
通讯作者: 魏太保 E-mail:weitaibao@126.com
基金资助:
国家自然科学基金（Nos.21661018，21662031，21574104）资助项目.

Study on the Effect of Host-Guest Based on the Dimethoxy-pillar[5]arene and Benzazole Heterocyclic Compounds

Shi Haixiong^a,b, Cheng Xiaobin^a, Lin Qi^a, Yao Hong^a, Zhang Youming^a, Wei Taibao^a

a Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070;
b College of Chemical Engineering, Lanzhou University of Arts and Science, Lanzhou 730000

Received:2017-12-26 Revised:2018-03-14 Published:2018-03-29
Contact: 10.6023/cjoc201712037 E-mail:weitaibao@126.com
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21661018, 21662031, 21574104).

1. Study on the Effect of Host-Guest Based on the Dimethoxy-pillar[5]arene and Benzazole Heterocyclic Compounds.PDF(6290KB)

Abstract

A host-guest system was successfully constructed from dimethoxypillar[5]arene (DMP5) and six guest molecules benzoazolidazole (G2), benzimidazole (G3) and benzothiazole (G1, G4, G5 and G6) via host-guest interactions and characterized by various techniques, including HRMS and ¹H NMR spectra. The result shows that heterocyclic compound was threaded into the cavity of pillar[5]arene to obtain host-guest system between DMpillar[5]arene and benzazole, forming inclusion complexes. Interestingly, the corresponding guest containing benzazole formed a stable host-guest complex with the same host. Moreover, the addition of guest compounds led to the effective reinforcement of the fluorescence intensity compared with the original guest species and the host (DMP5) that giving an additional support for the host-guest interaction based supramolecular assembly nature of the present system.

Key words: pillar[5]arenes, host-guest chemistry, assembly, benzazole heterocyclic compounds

Cite this article

Shi Haixiong, Cheng Xiaobin, Lin Qi, Yao Hong, Zhang Youming, Wei Taibao. Study on the Effect of Host-Guest Based on the Dimethoxy-pillar[5]arene and Benzazole Heterocyclic Compounds[J]. Chin. J. Org. Chem., 2018, 38(7): 1718-1724.

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[1] Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T. A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022.
[2] Cao, D.; Kou, Y.; Liang, J.; Chen, Z.; Wang, L.; Meier H. Angew. Chem., Int. Ed. 2009, 48, 9721.
[3] Ma, Y.; Zhang, Z.; Ji, X.; Han, C.; He, J.; Abliz, Z.; Chen, W.; Huang, F. Eur. J. Org. Chem. 2011, 2011, 5331.
[4] Han, C.; Zhang, Z.; Chi, X.; Zhang, M.; Yu, G.; Huang, F. Acta Chim. Sinica 2012, 70, 1775 (in Chinese).
(韩成友, 张子彬, 池小东, 张明明, 喻国灿, 黄飞鹤, 化学学报, 2012, 70, 1775.)
[5] Yue, S.; Zhou, Y.; Yao, Y.; Xue, M. Acta Chim. Sinica 2014, 72, 1053 (in Chinese).
(岳诗雨, 周玉娟, 姚勇, 薛敏, 化学学报, 2014, 72, 1053.)
[6] Yang, Y. W.; Sun, Y. L.; Song, N. Acc. Chem. Res. 2014, 47, 1950.
[7] Zhang, H.; Liu, Z.; Xin, F.; Hao, A. Chin. J. Org. Chem. 2012, 32, 219 (in Chinese).
(张华承, 刘召娜, 辛飞飞, 郝爱友, 有机化学, 2012, 32, 219.)
[8] Su, G.; Wu, D.; Li, Q.; Hou, J. Chin. J. Org. Chem. 2016, 36, 2130 (in Chinese).
(苏戈, 吴斗峰, 李巧伟, 侯军利, 有机化学, 2016, 36, 2130.)
[9] Li, C. Chem. Commun. 2014, 50, 12420.
[10] Yao, Y.; Xue, M.; Chen, J.; Zhang, M.; Huang, F. J. Am. Chem. Soc. 2012, 134, 15712.
[11] Si, W.; Chen, L.; Hu, X.-B.; Tang, G.; Chen, Z.; Hou, J.-L.; Li, Z.-T. Angew. Chem. 2011, 123, 12772.
[12] Duan, Q.; Cao, Y.; Li, Y.; Hu, X.; Xiao, T.; Lin, C.; Pan, Y.; Wang, L. J. Am. Chem. Soc. 2013, 135, 10542.
[13] Jiang, B.; Wang, W.; Zhang, Y.; Lu, Y.; Zhang, C.-W.; Yin, G.-Q.; Zhao, X.-L.; Xu, L.; Tan, H.; Li, X.; Jin, G.-X.; Yang, H.-B. Angew. Chem., Int. Ed. 2017, 56, 14438.
[14] Jiang, L.; Huang, X.; Chen, D.; Yan, H.; Li, X.; Du, X. Angew. Chem., Int. Ed. 2017, 56, 2655.
[15] Wei, T.-B.; Chen, J.-F. Cheng, X.-B.; Li, H.; Han, B.-B.; Zhang, Y.-M.; Yao, H.; Lin, Q. Org. Chem. Front. 2017, 4, 210.
[16] Lin, Q.; Mao, P.-P.; Fan, Y.-Q.; Liu, L.; Liu, J.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. Soft Matter 2017, 13, 7085.
[17] Wei, T.-B.; Chen, J.-F.; Cheng, X.-B.; Li, H.; Han, B.-B.; Yao, H.; Zhang, Y.-M.; Lin, Q. Polym. Chem. 2017, 8, 2005.
[18] Zhang, Y. M.; Shi, B. B.; Li, H.; Qu, W. J.; Gao, G. Y.; Lin, Q.; Yao, H.; Wei, T. B. Polym. Chem. 2014, 5, 4722.
[19] Lin, Q.; Jiang, X.-M.; Liu, L.; Chen, J.-F.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. Soft Matter. 2017, 13, 7222.
[20] Lin, Q.; Fan, Y.-Q.; Mao, P.-P.; Liu, L.; Liu, J.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. Chem.-Eur. J. 2018, 24, 777.
[21] Lin, Q.; Zhong, K.-P.; Zhu, J.-H.; Ding, L.; Su, J.-X.; Yao, H.; Wei, T.-B.; Zhang, Y.-M. Macromolecules 2017, 50, 7863.
[22] Li, Z.-Y.; Zhang, Y.; Zhang, C.-W.; Chen, L.-J. Wang, C.; Tan, H.; Yu, Y.; Li, X.; Yang, H.-B. J. Am. Chem. Soc. 2014, 136, 8577.
[23] Zhang, C.-W.; Ou, B.; Yin, G.-Q.; Chen, L.-J.; Yang, H.-B. Acta Polym. Sinica 2017, (1), 71 (in Chinese).
(张昌伟, 欧波, 尹光强, 陈丽君, 杨海波, 高分子学报, 2017, (1), 71.)
[24] Strutt, N. L.; Zhang, H.; Schneebeli, S. T.; Stoddart, J. F. Acc. Chem. Res. 2014, 47, 2631.
[25] Ogoshi, T.; Yamagishi, T.; Nakamoto, Y. Chem. Rev. 2016, 116, 7937.
[26] Wu, X.; Duan, Q.-P.; Ni, M.-F.; Hu, X.-Y.; Wang, L.-Y. Chin. J. Org. Chem. 2014, 34, 437 (in Chinese).
(吴旋, 段群鹏, 倪梦飞, 胡晓玉, 王乐勇, 有机化学, 2014, 34, 437.)
[27] Wang, Q.; Cheng, M.; Cao, Y.; Jiang, J.; Wang, L. Acta Chim. Sinica 2016, 74, 9 (in Chinese).
(王其, 程明, 曹逸涵, 强琚莉, 王乐勇, 化学学报, 2016, 74, 9.)
[28] 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.)
[29] Ogoshi, T.; Hashizume, M.; Yamagishi, T. A.; Nakamoto, Y. Chem. Commun. 2010, 46, 3708.
[30] Ma, Y.; Ji, X.; Xiang, F.; Chi, X.; Han, C.; He, J.; Abliz, Z.; Chen, W.; Huang, F. Chem. Commun. 2011, 47, 12340.
[31] Han, C.; Ma, F.; Zhang, Z.; Xia, B.; Yu, Y.; Huang, F. Org. Lett. 2010, 12, 4360.
[32] Li, C.; Chen, S.; Li, J.; Han, K.; Xu, M.; Hu, B.; Yu, Y.; Jia, X. Chem. Commun. 2011, 47, 11294.
[33] Liu, L.; Cao, D.; Jin, Y.; Tao, H.; Kou, Y.; Meier, H. Org. Biomol. Chem. 2011, 9, 7007.
[34] Shu, X.; Chen, S.; Li, J.; Chen, Z.; Weng, L.; Jia, X.; Li, C. Chem. Commun. 2012, 48, 2967.
[35] Liu, L.; Duan, W.; Kou, Y.; Wang, L.; Meier, H.; Cao, D. Chin. J. Chem. 2015, 33, 346.
[36] Wu, G.-Y.; Shi, B.-B.; Lin, Q.; Li, H.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. RSC Adv. 2015, 5, 4958.
[37] Lin, Q.; Liu, L.; Zheng, F.; Mao, P.-P.; Liu, J.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. Tetrahedron 2017, 73, 5307.
[38] Lin, Q.; Zheng, F.; Liu, L.; Mao, P.-P.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. RSC Adv. 2016, 6, 111928.
[39] Lin, Q.; Mao, P.-P.; Zheng, F.; Liu, L.; Liu, J.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. New J. Chem. 2017, 41, 12172.
[40] Lin, Q.; Lu, T.-T.; Zhu, X.; Wei, T.-B.; Li, H.; Zhang, Y.-M. Chem. Sci. 2016, 7, 5341.
[41] Chen, J.-F.; Lin, Q.; Zhang, Y.-M.; Yao, H.; Wei, T.-B. Chem. Commun. 2017, 53, 13296.
[42] Wei, T.-B.; Cheng, X.-B.; Li, H.; Zheng, F.; Lin, Q.; Yao, H.; Zhang, Y.-M. RSC Adv. 2016, 6, 20987.

甲氧基柱[5]芳烃对苯并唑类杂环化合物的主客体作用研究

Study on the Effect of Host-Guest Based on the Dimethoxy-pillar[5]arene and Benzazole Heterocyclic Compounds

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