Convenient synthesis of [3]catenane by olefin metathesis dimerizations

Hydrogen-Bond-Mediated Template Synthesis of Rotaxanes, Catenanes, and Knotanes

“…In what was coined a "magic ring" experiment, Grubbs et al were able to demonstrate the reaction to be reversible. Starting with a closed macrocycle containing a double bond, the incorporation of the axle occurred with almost quantitative yields when a metathesis catalyst was added.A similar approach to [3]catenanes was recently reported [106]. (iii) The formation of disulfide bridges can be used to connect two pseudorotaxanes whose axle bears one stopper and is terminated at the opposite end by a thio group.…”

Highly efficient synthesis of [3]rotaxane assisted by preorganisation of pseudorotaxane using bis(crown ether)s

“…12 We previously reported that the olefin metathesis reaction provided a powerful tool to prepare [3]catenane. 13 In the course of this study, the metathesis reaction has been applied to the synthesis of rotaxane. 14 Inspired by the concept of preorganization, we describe here a full account of tether-assisted synthetic methodology of [3]rotaxane via olefin metathesis.…”

Self‐Assembly with Block Copolymers through Metal Coordination of SCS–PdII Pincer Complexes and Pseudorotaxane Formation

“…The hydrogen-bonding system is based on the threading of a dialkyl-A C H T U N G T R E N N U N G ammonium cation 2 into a dibenzo [24]crown-8 (DB24C8) macrocyle 3 to form a pseudorotaxane. [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42] Since the discovery of rotaxane formation resulting from the threading of an ammonium cation into a crown ether macrocycle in 1995, [43] a number of interactions between ammonium cat-A C H T U N G T R E N N U N G ions and crown ether macrocycles have been studied, result-ing in a myriad of supramolecular structures [44][45][46][47][48][49][50] and the evolution [51] of a "molecular meccano kit". The driving force for the formation of threadlike structures from dialkylammonium cations and crown ether macrocyles is the formation of strong hydrogen bonds between the acidic NH 2 + protons and the oxygen atoms in the ring of the crown ether macrocyle.…”