Abstract
Getting connected: The formation of pseudorotaxane assemblies between a designed macrocyclic halogen bonding (XB) acceptor (red in scheme) and a series of XB donor threading components was templated by a single halogen bond. The strength of the XB assembly between the pyridine macrocycle and iodopyridinium thread was utilized in the ring-closing metathesis clipping synthesis of a [2]catenane.
Highlights
Interlocked molecules have captured chemists imagination owing to their nontrivial topology and the promise of their potential nanotechnological uses as molecular machines[1] and in chemical sensor applications.[2]
By incorporating a suitable neutral Lewis base XB acceptor, such as pyridine,[7b,9] into a macrocyclic framework, we demonstrate that a single charge-assisted XB interaction can be utilized for pseudorotaxane assembly and, importantly, in the synthesis of a novel interlocked catenane
An acyclic positively charged XB-donor component threads through a complementary XBaccepting pyridine-containing macrocycle, thereby forming an orthogonal interpenetrative assembly that is stabilized by a charge-assisted XB interaction
Summary
Interlocked molecules have captured chemists imagination owing to their nontrivial topology and the promise of their potential nanotechnological uses as molecular machines[1] and in chemical sensor applications.[2]. A range of bromo- and iodofunctionalized triazolium and pyridinium compounds were chosen as potential threading components, containing terminal vinyl functional groups, which after successful pseudorotaxane assembly with macrocycle 1, could be used for catenane synthesis through ring-closing metathesis (RCM) cyclization (Scheme 1).
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