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Design and synthesis of a bis-macrocyclic host and guests as building blocks for small molecular knots.

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.

SUBMITTER: Margolis EA

PROVIDER: S-EPMC7509378 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Design and synthesis of a bis-macrocyclic host and guests as building blocks for small molecular knots.

Margolis Elizabeth A EA Keyes Rebecca J RJ Lockey Stephen D SD Fenlon Edward E EE

Beilstein journal of organic chemistry 20200918

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 s ...[more]

PMID: 33014171

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