Self-Assembly Modes of Three Cucurbit[n] urils with Benzoindazole Derivative

doi:10.6023/cjoc201807047

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (11): 3094-3100.DOI: 10.6023/cjoc201807047 Previous Articles Next Articles

Special Issue: 有机小分子-金属协同催化；有机超分子化学合辑

Notes

三种瓜环与苯并吲唑衍生物的超分子自组装

王海燕^a, 阚京兰^b, 边炳^c, 陈青^a, 陶朱^a, 肖昕^a

a 贵州大学贵州省大环化学及超分子化学重点实验室贵阳 550025;
b 山东师范大学化学化工与材料科学学院济南 250014;
c 山东科技大学化学与环境工程学院青岛 266590

收稿日期:2018-07-26 修回日期:2018-09-11 发布日期:2018-10-12
通讯作者: 肖昕 E-mail:gyhxxiaoxin@163.com
基金资助:
国家自然科学基金（Nos.21561007，21861011）、贵州省科学基金（No.2016-1030）、贵州省高层次创新型人才培养计划（No.2016-5657）和贵州省教育厅创新群体重大研究（No.2017-028）资助项目.

Self-Assembly Modes of Three Cucurbit[n] urils with Benzoindazole Derivative

Wang Haiyan^a, Kan Jinglan^b, Bian Bing^c, Chen Qing^a, Tao Zhu^a, Xiao Xin^a

a Key Laboratory of Macrocyclic and Supramolecular Chenmistry of Guizhou Province, Guizhou University, Guiyang 550025;
b College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014;
c College of Chemistry and Environmental Engineering, Shandong University of Science and Technology, Qingda 266590

Received:2018-07-26 Revised:2018-09-11 Published:2018-10-12
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21561007, 21861011), the Science and Technology Fund of Guizhou Province (No. 2016-1030), the Innovation Program for High-Level Talents of Guizhou Province (No. 2016-5657) and the Major Program for Creative Research Groups of Guizhou Provincial Education Department (No. 2017-028).

1. Self-Assembly Modes of Three Cucurbit[n] urils with Benzoindazole Derivative.PDF(878KB)

Abstract

A pharmaceutical intermediate, 3-pyridyl benzoxazole derivatives (DIHY), was designed and synthesized as the guest molecule. The self-assembly binding models of tetramethyl cucurbit[6] uril (TMeQ[6]), cucurbit[7] uril (Q[7]) and cucurbit[8] uril (Q[8]) with DIHY were investigated by ¹H NMR, MS, isothermal titration calorimetry and UV-Vis spectrum. The results showed that there are different modes of interaction between these three different cucurbit[n] uril and DIHY. For the TMeQ[6]-DIHY system, the guest molecule is located at the port of the TMeQ[6], while for the Q[7]-DIHY system, the 4,5-dihydro-2H-benzoxazole moiety of the guest molecule reside within the cavity of Q[7] host, whereas the pyridyl group of DIHY guest remains outside of the portal to form the 1:1 inclusion complexes of pseudorotaxane structure. Nevertheless, the 4,5-dihydro-2H-benzoxazole moiety of two guest molecule is included in the cavity of Q[8] host in a "face to face" stacking way, while the pyridine group of DIHY is located at the port of Q[8] to form a 1:2 supramolecular structure.

Key words: cucurbit[n]uril, pseudorotaxane, supramolecular

Cite this article

Wang Haiyan, Kan Jinglan, Bian Bing, Chen Qing, Tao Zhu, Xiao Xin. Self-Assembly Modes of Three Cucurbit[n] urils with Benzoindazole Derivative[J]. Chin. J. Org. Chem., 2018, 38(11): 3094-3100.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Liu, S. M.; Kim, K.; Isaacs, L. J. Org. Chem. 2007, 72, 6840.
(b) Isaacs, L. Chem. Commun. 2009, 619.
(c) Bai, D.; Wang, X.; Gao, Z. Z.; Qiu, S. C.; Tao, Z. Chin. J. Org. Chem. 2017, 37, 245(in Chinese). (白东, 王新, 高中政, 邱胜超, 陶朱, 张建新, 肖昕, 有机化学, 2017, 37, 245.)
(d) Yi, J. M.; Chen, M. H.; Xue, S. F.; Tao, Z. Chin. J. Org. Chem. 2016, 36, 653(in Chinese). (易君明, 陈明华, 薛赛凤, 陶朱, 有机化学, 2016, 36, 653.)
(e) Xiao, X.; Liu, J. X.; Fan, Z. F.; Chen, K.; Zhu, Q. J.; Xue, S. F.; Tao, Z. Chem. Commun. 2010, 46, 3741.
(f) Huang, Y.; Tao, Z.; Xue, S. F.; Zhu, Q. J. Chem. J. Chin. Univ. 2011, 32, 2022(in Chinese). (黄英, 陶朱, 薛赛凤, 祝黔江, 高等学校化学学报, 2011, 32, 2022.)
(g) Guo, Q. H.; Zhao L.; Wang, M. X. Angew. Chem., Int. Ed. 2015, 54, 8386.
(h) Li, C. J.; Xu, Q. Q.; Li, J.; Fei N. Y.; Jia, X. S. Org. Biomol. Chem. 2010, 8, 1568.
(i) Chen, H. Q.; Fan, J. Z.; Hu, X. S.; Ma, J. W.; Wang, S. L.; Li, J.; Yu, Y. H.; Jia, X. S.; Li, C. J. Chem. Sci. 2015, 6, 197.
[2] (a) Huang, Y.; Tao, Z.; Xue, S. F.; Zhu, Q. J. Chem. J. Chin. Univ. 2011, 32, 2022(in Chinese). (黄英, 陶朱, 薛赛凤, 祝黔江, 高等学校化学学报, 2011, 32, 2022.)
(c) Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H. J.; Kim, K. Acc. Chem. Res. 2003, 36, 62.
(d) Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 127, 16798.
(e) Kim, K.; Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, D. J. Chem. Soc. Rev. 2007, 36, 267.
(f) Xiao, X.; Wu, M. Q.; Xue, S. F.; Zhu, Q. J.; Zhang, J. X.; Tao, Z. Chin. J. Org. Chem. 2012, 33, 68(in Chinese). (肖昕, 吴明强, 薛赛凤, 祝黔江, 张建新, 陶朱, 有机化学, 2012, 33, 68.)
(g) Dong, N.; Wang, X. L.; Pan, J. P.; Tao, Z. Acta Chim. Sinica 2011, 69, 1431(in Chinese). (董南, 王秀林, 盘金品, 陶朱, 化学学报, 2011, 69, 1431.)
(h) Wu, K.; Zhao, X.; Chen, M.; Zhang, H.; Liu, Z.; Zhang, X.; Zhu, X.; Liu, Q. New J. Chem. 2018, 42, 9578.
(i) Dong, N.; Xue, S. F.; Tao, Z.; Zhao, Y.; Cai, J.; Liu, H. C. Acta Chim. Sinica 2008, 66, 1117(in Chinese). (董南, 薛赛凤, 陶朱, 赵昱, 蔡洁, 刘洪材, 化学学报, 2008, 66, 1117.)
[3] (a) Isaacs, L.; Park, S. K.; Liu, S.; Ko, Y. H.; Selvapalam, N.; Kim, Y.; Kim, H.; Zavalij, P. Y.; Kim, G. H.; Lee, H. S.; Kim, K. J. Am. Chem. Soc. 2005, 127, 18000.
(b) Ding, Y.; Yang, B.; Liu, H.; Liu, Z.; Zhang, X.; Zheng, X.; Liu, Q. Sens. Actuators, B 2018, 259, 775.
(c) Bai, D.; Zhou, Y.; Lu, J. H.; Liu, Q. Y.; 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.)
(d) Barrow, S. J.; Kasera, S.; Rowland, M. J.; Barrio, D. J.; Scherman, O. A. Chem. Rev. 2015, 115, 12320.
(e) Assaf, K. I.; Nau, W. M. Chem. Soc. Rev. 2015, 44, 394.
(f) Xiao, X.; Tu, S. C.; Xue, S. X.; Zhu, Q. J.; Tao, Z.; Zhang, J. X.; Wei, G. Chem. J. Chin. Univ. 2013, 34, 354(in Chinese). (肖昕, 涂仕春, 薛赛凤, 祝黔江, 陶朱, 张建新, 卫钢, 高等学校化学学报, 2013, 34, 354.)
(g) Kaifer, A. E. Acc. Chem. Res. 2014, 47, 2160.
(h) Wang, J.; Zhou, Q. L.; Yan, X. H. Acta Chim. Sinica 2017, 75, 933(in Chinese). (王娟, 邹千里, 闫学海, 化学学报, 2017, 75, 933.)
(i) Sun, Q. H.; Li, Z.; Ma, N. Acta Chim. Sinica 2018, 76, 43(in Chinese). (孙权洪, 李智, 马楠, 化学学报, 2018, 76, 43.)
[4] (a) Xin, J. H.; Yang, L. Y.; Li, Q.; Zhou, J. P.; Zhang, H. B. Prog. Pharm. Sci. 2014, 38, 174(in Chinese). (邢峻豪, 杨凌云, 李清, 周金培, 张惠斌, 药学进展, 2014, 38, 174.)
(b) Wang, X. F.; Chen, N. W.; Wang, W. Chin. J. Rehabil. Theory Pract. 2010, 16, 954(in Chinese). (王晓锋, 陈乃宏, 王文, 中国康复理论与实践, 2010, 16, 954.)
(c) Bates, E. R.; Lau, W. C.; Angiolillo, D. J. J. Am. Coll. Cardiol. 2011, 57, 1251.
[5] Liou, J. P.; Chang, Y. L.; Kuo, F. M. J. Med. Chem. 2004, 47, 4247.
[6] Duan, J. X.; Cai, X.; Meng, F. J. Med. Chem. 2007, 50, 1001.
[7] Tung, Y. S.; Coumar, M. S.; Wu, Y. S. J. Med. Chem. 2011, 54, 3076.
[8] Gao, Z. Z.; Yang, L. G.; Bai, D.; Chen, L. X.; 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.)

[1]	Lijuan Xiao, Yanping Zhang, Miao Hong. Research Progress of Lewis Acid and Base Pairs Applied in Materials Chemistry [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 949-960.
[2]	Fen Li, Chuanzhi Liu, Zhiyuan Hu, Panpan Luo, Rongzheng Cui, Yanke Huang, Xinming Liu, Lantao Liu, Wei Wu. Intermolecular Halogen and Hydrogen Bonding-Controlled Self-Assembly of Network Structures [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 705-711.
[3]	Huiming Lu, Lamaocao Ma, Hengchang Ma. Research Progress and Prospect of Aggregation-Induced Emission Supramolecular Luminescence Materials [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4075-4105.
[4]	Ze-Kun Wang, Zi-Yue Xu, Juan-Juan Li, Shang-Bo Yu, Hui Wang, Dong-Sheng Guo, Dan-Wei Zhang, Zhan-Ting Li. Gradient Enhancement of Supramolecular Organic Framework for Solubilization of Hydrophobic Molecules by Two Molecular Containers in Water [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2236-2242.
[5]	Jingjing Guo, Minjie Guo. Progress in Design and Application of Supramolecular Fluorescent Systems Based on Difluoroboron-Dipyrromethene and Macrocyclic Compounds [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2946-2963.
[6]	Hongyu Qian, Pin He, Lu Zhang, Ke Chen, Binbin Xu, Shaoliang Lin. Synthesis and Photo-responsive Self-Assembly of Azobenzene-Containing Molecular Brushes [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2891-2897.
[7]	Changxing Ji, Guangxia Wang, Hua Wang. Progress in Metal-Organic Supramolecular System Based on Subcomponent Self-Assembly [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2261-2279.
[8]	Jinguo Liu, Feng Yin, Jun Hu, Yong Ju. Fabrication and Applications of Supramolecular Chiral Assemblies [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1031-1052.
[9]	Qiang Pei, Aixiang Ding, Jinjin Wu. Supramolecular Assemblies Based on Intramolecular Three-Center Hydrogen Bond and their Applications [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 105-125.
[10]	Yan Zi'ang, Zou Lei, Ma Xiang. Recent Advances in Pure Organic Luminescent Supramolecular Materials [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1814-1822.
[11]	Xiao Tangxin, Zhou Ling, Wei Xiaoyan, Li Zhengyi, Sun Xiaoqiang. Supramolecular Copolymers Driven by Quadruple Hydrogen Bonding and Host-Guest Interactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 944-949.
[12]	Qi Lijie, Ding Yihan, Xiao Tangxin, Wu Haoran, Diao Kai, Bao Cheng, Shen Yong, Li Zhengyi, Sun Xiaoqiang, Wang Leyong. Supramolecular Self-Assembly of Dioxyphenylene Bridged Ureidopyrimidinone Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3847-3852.
[13]	Li Jing, Han Ying, Chen Chuanfeng. Recent Advances in Novel Macrocyclic Arenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3714-3737.
[14]	Zhang Yi, Liu Yu. Supramolecular Assemblies of Multi-Charged Cyclodextrins [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3802-3811.
[15]	Wang Jiao, Yao Hong, Zhou Qi, Kan Xiaotong, Fan Yanqing, Guan Xiaowen, Zhang Youming, Lin Qi, Wei Taibao. Molecule-Responsive Supramolecular Hydrogel Constructed from Pillar[5]arene Based on Host-Guest System [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 175-180.

三种瓜环与苯并吲唑衍生物的超分子自组装

Self-Assembly Modes of Three Cucurbit[n] urils with Benzoindazole Derivative

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments