Department of Chemistry, Faculty of Science, Hokkaido University, Kita-ku, Sapporo, Japan.
Chemistry. 2012 Oct 22;18(43):13722-32. doi: 10.1002/chem.201200837. Epub 2012 Sep 20.
Imine-bridged rotaxanes are a new type of rotaxane in which the axle and macrocyclic ring are connected by imine bonds. We have previously reported that in imine-bridged rotaxane 5, the shuttling motion of the macrocycle could be controlled by changing the temperature. In this study, we investigated how the axle and macrocycle structures affect the construction of the imine-bridged rotaxane as well as the dynamic equilibrium between imine-bridged rotaxane 5 and [2]rotaxane 7 by using various combinations of axles (1 A,B), macrocycles (2 a-e), and side-stations (XYL and TEG). In the threading process, the flexibility of the macrocycle and the substituent groups at the para position of the aniline moieties affect the preparation of the threaded imines. The size of the imine-bridging station and the macrocyclic tether affects the hydrolysis of the imine bonds under acidic conditions.
亚胺键桥联轮烷是一种新型轮烷，其中轮烷和大环通过亚胺键连接。我们之前曾报道过，在亚胺键桥联轮烷 5 中，通过改变温度可以控制大环的穿梭运动。在这项研究中，我们通过使用各种轴（1A、B）、大环（2a-e）和侧基（XYL 和 TEG）的组合，研究了轴和大环结构如何影响亚胺键桥联轮烷的构建以及亚胺键桥联轮烷 5 和[2]轮烷 7 之间的动态平衡。在穿线过程中，大环的柔韧性和苯胺部分对位取代基影响了穿线亚胺的制备。亚胺桥联站和大环系绳的大小影响酸性条件下亚胺键的水解。
