Jia Fei, He Zhenfeng, Yang Liu-Pan, Pan Zhi-Sheng, Yi Min, Jiang Ren-Wang, Jiang Wei
Department of Chemistry , South University of Science and Technology of China , No. 1088 Xueyuan Blvd, Nanshan District , Shenzhen , 518055 , P. R. China . Email:
Institute of Traditional Chinese Medicine and Natural Products , College of Pharmacy , Jinan University , Guangzhou 510632 , P. R. China.
Chem Sci. 2015 Dec 1;6(12):6731-6738. doi: 10.1039/c5sc03251b. Epub 2015 Sep 14.
There are a large number of synthetic macrocyclic receptors in the literature. No particular one is suitable for all guests or purposes. For a broader guest binding scope or multiple purposes, a macrocycle with multiple interconvertible cavities will be advantageous. Here, we report a naphthalene-based macrocyclic receptor with an adaptable cavity, namely oxatub[4]arene. It has four representative conformations resulting from the flipping of naphthalene rings, each with a deep and well-defined cavity. Different guests select one host conformer or a combination of conformers. All the four conformers have been detected and characterized based on 2D NMR spectra and X-ray single crystal structures. Thermodynamically, these conformers constitute a reservoir, that responds to the structural changes of guests, and thus maximizes the association free energies. This smart macrocycle may provide a new platform for the construction of molecular machines and devices or stimuli-responsive materials.
文献中有大量的合成大环受体。没有一种特定的受体适用于所有客体或用途。对于更广泛的客体结合范围或多种用途，具有多个可相互转换空腔的大环将具有优势。在此，我们报道了一种具有可适应空腔的基于萘的大环受体，即氧杂[4]芳烃。它具有因萘环翻转而产生的四种代表性构象，每种构象都有一个深且明确的空腔。不同的客体选择一种主体构象或构象的组合。基于二维核磁共振光谱和X射线单晶结构，已检测并表征了所有四种构象。从热力学角度来看，这些构象构成了一个库，它对客体的结构变化做出响应，从而使缔合自由能最大化。这种智能大环可能为构建分子机器和器件或刺激响应材料提供一个新平台。
