Supramolecular compounds from multiple ugi multicomponent macrocyclizations: peptoid-based cryptands, cages, and...

Area of Science:

• Supramolecular Chemistry
• Organic Synthesis
• Materials Science

Background:

• Developing efficient synthetic routes for complex macromulticyclic structures like cryptands, cages, and cryptophanes is crucial for advancing supramolecular chemistry.
• Trifunctional building blocks offer versatile platforms for constructing intricate molecular architectures.
• The synthesis of receptors with tailored recognition motifs is key for applications in catalysis and coordination chemistry.

Purpose of the Study:

• To develop the first 3-fold multicomponent macrocyclizations for synthesizing cryptands, cages, and cryptophanes.
• To create a straightforward, efficient, and diversity-oriented method for producing complex macromulticycles.
• To enable the construction of combinatorial libraries of synthetic receptors with potential applications.

Main Methods:

• Utilized trifunctional building blocks in a one-pot, 3-fold multicomponent macrocyclization strategy.
• Incorporated peptoid tethers with additional recognition motifs into the macrocyclic structures.
• Developed a method for forming up to 20 new bonds in a single synthetic step.

Main Results:

• Successfully synthesized cryptands, cages, and cryptophanes with peptoid tethers and recognition motifs.
• Demonstrated the efficiency and diversity-oriented nature of the developed macrocyclization strategy.
• Achieved the formation of up to 20 new bonds in one pot, creating complex macromulticyclic cavities.
• Showcased the ability to create asymmetric macromulticyclic cavities.

Conclusions:

• The developed 3-fold multicomponent macrocyclization is a powerful tool for accessing complex macromulticycles.
• This strategy is suitable for building combinatorial libraries of synthetic receptors for various applications.
• The method offers a straightforward and efficient route to diverse supramolecular structures.