摘要/Abstract

设计、合成了医药中间体3-吡啶基苯并吲唑衍生物（DIHY）作为客体分子，并利用¹H NMR、质谱、等温量热滴定和紫外吸收光谱法考察了主体对称四甲基六元瓜环（TMeQ[6]）、七元瓜环（Q[7]）以及八元瓜环（Q[8]）和与其相互作用的结构特征.结果表明，这三种具有不同空腔大小的瓜环与DIHY之间具有不同的作用模式.TMeQ[6]-DIHY体系中，客体分子位于瓜环的端口处；Q[7]-DIHY体系中，客体分子DIHY的4，5-二氢-2H-苯并吲唑部分进入到瓜环的空腔内部，而吡啶基团位于瓜环的端口形成1：1的类轮烷结构；Q[8]-DIHY体系中，2个客体分子DIHY的4，5-二氢-2H-苯并吲唑部分以"面对面"的堆叠方式进入到Q[8]的空腔中，而吡啶基团位于瓜环的端口，自组装形成1：2的超分子结构.
关键词: 瓜环, 类轮烷, 超分子
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


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