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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

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Chiral, sequence-definable foldamer-derived macrocycles.

Toyah M C Warnock¹, Sundaram Rajkumar², Matthew P Fitzpatrick¹

¹School of Chemistry and Chemical Engineering, Queen's University Belfast David Keir Building Belfast BT9 5AG UK p.knipe@qub.ac.uk.

Chemical Science

|January 10, 2022

Summary

This summary is machine-generated.

Chemists created new cyclic foldamers inspired by nature. Macrocyclization of foldamer precursors yielded chiral trimers and tetramers with potential for cation binding.

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Area of Science:

Supramolecular Chemistry
Organic Chemistry
Chemical Synthesis

Background:

Foldamers are synthetic oligomers inspired by natural macromolecules.
Macrocyclization is a common strategy in nature for stabilizing conformation but is underexplored in foldamer chemistry.
Developing novel foldamer architectures is crucial for advancing molecular design.

Purpose of the Study:

To introduce a new class of chiral cyclic foldamers through macrocyclization.
To explore different synthetic strategies for creating cyclic foldamers with controlled sequences.
To investigate the structural and functional properties of these novel macrocycles.

Main Methods:

Synthesis of open-chain foldamer precursors.
Macrocyclization via [2 + 2] self-assembly for symmetrical products.
Linear synthesis and cyclization for unsymmetrical trimers.
Structural characterization using X-ray crystallography and Density Functional Theory (DFT) calculations.

Main Results:

Successfully synthesized novel chiral cyclic trimers and tetramers.
Demonstrated controlled synthesis of both symmetrical and unsymmetrical cyclic foldamers.
Determined the distinct conformations of tetramers (near-planar) and trimers (shallow bowl-like).
Showcased the cation-binding capabilities of the macrocycles in a proof-of-concept experiment.

Conclusions:

Macrocyclization is a viable and effective strategy for creating conformationally stabilized foldamers.
The developed cyclic foldamers exhibit unique structural features and functional properties.
These novel macrocycles hold promise for applications in areas such as molecular recognition and sensing.