In this two-session experiment for an organic chemistry lab, students prepare a macrocyclic host compound─namely, a pillar[5]arene─by means of a templated 1,4-dimethoxybenzene/formaldehyde cyclo-oligomerization (session 1), and then, they explore its molecular recognition properties toward the 1,8-diaminooctane guest with the aid of ¹H NMR spectroscopy (session 2). The acid-catalyzed synthesis of decamethyl-pillar[5]arene provides, in good yield, a product sufficiently pure to be directly used in the subsequent NMR titration experiment. The two-session experiment targets advanced chemistry students, whereas the 4 h synthesis of the macrocycle (session 1) may be included in an introductory organic chemistry laboratory course. This experiment links concepts spanning from classical S_EAr reactions to macrocycle synthesis down to host–guest chemistry, NMR spectroscopy, and data treatment, providing a useful connection between organic chemistry synthesis and supramolecular chemistry.

中文翻译：

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十甲基柱[5]芳烃：合成及识别性质

在这个有机化学实验室的两节实验中，学生通过模板化 1,4-二甲氧基苯/甲醛环低聚制备大环主体化合物（即柱[5]芳烃）（第 1 节），然后，他们借助¹ H NMR 光谱探索了其对 1,8-二氨基辛烷客体的分子识别特性（第 2 部分）。十甲基柱[5]芳烃的酸催化合成以良好的收率提供了足够纯的产物，可直接用于后续的 NMR 滴定实验。两节实验针对的是高级化学学生，而 4 小时的大环合成（第 1 节）可能包含在介绍性有机化学实验室课程中。该实验将经典 S _E Ar 反应、大环合成、主客体化学、核磁共振波谱和数据处理等概念联系起来，在有机化学合成和超分子化学之间提供了有用的联系。