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

Corresponding author: Xiao Xin, gyhxxiaoxin@163.com
Received Date: 26 July 2018
Revised Date: 11 September 2018
Available Online: 14 November 2018
Fund Project: the Science and Technology Fund of Guizhou Province 2016-1030the National Natural Science Foundation of China 21561007Project 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)the National Natural Science Foundation of China 21861011the Innovation Program for High-Level Talents of Guizhou Province 2016-5657the Major Program for Creative Research Groups of Guizhou Provincial Education Department 2017-028

Figures(7)

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.

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

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