Design and synthesis of a bis-macrocyclic host and guests as building blocks for small molecular knots
Elizabeth A Margolis1, Rebecca J Keyes1, Stephen D Lockey1
1Department of Chemistry, Franklin & Marshall College, PO Box 3003, Lancaster, PA 17601, USA.
Abstract:
The thread-link-cut (TLC) approach has previously shown promise as a novel method to synthesize molecular knots. The modular second-generation approach to small trefoil knots described herein involves electrostatic interactions between an electron-rich bis-macrocyclic host compound and electron-deficient guests in the threading step. The bis-macrocyclic host was synthesized in eight steps and 6.6% overall yield. Ammonium and pyridinium guests were synthesized in 4-5 steps. The TLC knot-forming sequence was carried out and produced a product with the expected molecular weight, but, unfortunately, further characterization did not produce conclusive results regarding the topology of the product.
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction


