Kaizerman-Kane Dana, Hadar Maya, Tal Noam, Dobrovetsky Roman, Zafrani Yossi, Cohen Yoram
School of Chemistry, Sackler Faculty of Exact sciences, Tel Aviv University, Ramat Aviv, 69978, Tel Aviv, Israel.
Department of Organic Chemistry, Israel Institute for Biological Research, Ness-Ziona, 740000, Israel.
Angew Chem Int Ed Engl. 2019 Apr 8;58(16):5302-5306. doi: 10.1002/anie.201900217. Epub 2019 Mar 14.
We describe the preparation of the first water-soluble pH-responsive supramolecular hexagonal boxes (SHBs) based on multiple charge-assisted hydrogen bonds between peramino-pillar[6]arenes 2 with the molecular "lid" mellitic acid (1 a). The interaction between 2 and 1 a, as well as the other "lids" pyromellitic and trimesic acids (1 b and 1 c, respecively) were studied by a combination of experimental and computational methods. Interestingly, the addition of 1 a to the complexes of the protonated form of pillar[6]arene 2, that is, 3, with bis-sulfonate 4 a or 4 b, immediately led to guest escape along with the formation of closed 1 a 2 supramolecular boxes. Moreover, the process of the openning and closing of the supramolecular boxes along with threading and escaping of the guests, respectively, was found to be reversible and pH-responsive. This study paves the way for the easy and modular preparation of different SHBs that may have myriad applications.
我们描述了基于全氨基柱[6]芳烃2与分子“盖子”苯六甲酸（1a）之间的多重电荷辅助氢键制备首个水溶性pH响应超分子六角盒（SHB）的过程。通过实验和计算方法相结合，研究了2与1a以及其他“盖子”均苯四甲酸和偏苯三酸（分别为1b和1c）之间的相互作用。有趣的是，将1a添加到质子化形式的柱[6]芳烃2（即3）与双磺酸盐4a或4b的配合物中，会立即导致客体逸出，并形成封闭的1a 2超分子盒。此外，发现超分子盒的打开和关闭过程分别伴随着客体的穿入和逸出，是可逆的且对pH有响应。这项研究为简便且模块化地制备可能具有多种应用的不同SHB铺平了道路。
