Construction of mechanically interlocked molecules (MIMs) with highly complexed structure has been remarkably concerned by synthetic chemists. Recently, Prof. Da-Hui Qu group achieved remarkable advance in one-pot synthesis of daisy-chain-containing hetero[4]rotaxane. A paper entitled “One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy” (http://pubs.rsc.org/is/content/articlehtml/2016/sc/c5sc04844c) was published in Chemical Science (2016, 7, 1696) and highlighted as an inside front cover.
MIMs have attracted much attention of synthetic chemists due to the unique interlocked structure. However, little effort has focused on the successful synthesis of a [c2]daisy-chain-containing hetero[n]rotaxane in an efficient and facile one-pot mode, in which the difficulty lies in the “selective” self-assembly in a system simultaneously involving both threading and interpenetration. In this work, three key intermediates are employed to synthesize the target products, and the “self-sorting” behavior among these intermediates provides significant and efficient possibility in making the self-assembly process efficient and homogeneous as a single mode. Subsequent CuAAC click reaction in one pot can obtain the highly symmetrical hetero[4]rotaxane. This self-sorting strategy supports significant methodology for construction of MIMs with highly complexity in structure.
This work was completed by Xin Fu and Qi Zhang collectively. The work was supported by the National Basic Research Program of China, Science Fund for Creative Research Groups.