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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Published on: September 28, 2022

Macrocyclic pentamers functionalised around their periphery as potential building blocks.

Seong Nam¹, David C Ware¹, Penelope J Brothers^1,2

¹School of Chemical Sciences, University of Auckland Private Bag 92019 Auckland 1142 New Zealand p.brothers@auckland.ac.nz.

|May 6, 2022

Summary

Researchers developed a novel five-fold symmetric macrocyclic aromatic pentamer. This fluorine-substituted macrocycle, synthesized in a one-pot procedure, offers potential as pentagonal building blocks for further functionalization.

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Area of Science:

Supramolecular Chemistry
Organic Synthesis
Materials Science

Background:

Macrocyclic compounds are crucial in supramolecular chemistry.
Aromatic pentamers offer unique structural properties.
Existing synthesis methods for such structures can be complex and inefficient.

Purpose of the Study:

To synthesize a novel five-fold symmetric macrocyclic aromatic pentamer.
To introduce peripheral benzyloxy and hydroxyl groups for further functionalization.
To develop an improved, one-pot synthesis method.

Main Methods:

One-pot synthesis of a fluorine-substituted macrocycle.
Utilizing a five-fold symmetric aromatic pentamer core.
Incorporating peripheral benzyloxy and hydroxyl functionalities.

Main Results:

Successful synthesis of the target macrocyclic aromatic pentamer.
Demonstration of a one-pot procedure, improving upon literature methods.
Creation of a molecule with potential as a pentagonal building block.

Conclusions:

The developed one-pot method is an efficient route to the five-fold symmetric macrocyclic aromatic pentamer.
The synthesized macrocycle provides a platform for further functionalization.
This work contributes to the development of novel building blocks for advanced materials.