Ultramacrocyclization via selective catenation in water

Area of Science:

• Supramolecular Chemistry
• Organic Chemistry

Background:

• Macrocyclic compounds are crucial in various scientific fields.
• Synthesizing large macrocycles, especially in water, presents significant challenges.

Purpose of the Study:

• To develop a novel method for synthesizing ultra-large macrocycles.
• To demonstrate the feasibility of ultramacrocyclization in aqueous media.

Main Methods:

• Self-assembly of cyclic [2]catenane dimers via selective hydrazone condensation.
• Utilizing both one-pot and post-functionalization strategies.
• Employing aqueous media for the synthesis.

Main Results:

• Successfully synthesized two distinct cyclic [2]catenane dimers.
• Each dimer consists of two 36-membered rings, forming an ultra-large macrocycle (>50 atoms).
• Demonstrated efficient cyclization in pure water.

Conclusions:

• Catenation provides a novel and effective strategy for ultramacrocyclization.
• Hydrazone condensation in aqueous media is a viable route for constructing complex macrocyclic architectures.
• This approach opens new avenues for designing and synthesizing large molecular structures in environmentally friendly conditions.