Building Covalent Molecular Capsules by Thiol-Michael Addition Click Reaction

Area of Science:

• Supramolecular Chemistry
• Organic Synthesis
• Click Chemistry

Background:

• Thiol-Michael addition (TMA) is an underutilized click chemistry reaction.
• Complex molecular architectures are crucial in supramolecular chemistry.
• Efficient methods for constructing covalent cages and capsules are needed.

Purpose of the Study:

• To develop a rapid and efficient method for synthesizing covalent molecular capsules using TMA.
• To explore the application of TMA in constructing complex supramolecular structures.
• To introduce a sequential click reaction strategy for advanced molecular assembly.

Main Methods:

• Utilizing the thiol-Michael addition (TMA) click reaction for covalent bond formation.
• Employing common supramolecular scaffolds like calixarenes, CTV, and cavitands.
• Developing a 'click&click' sequential procedure combining TMA and copper-catalyzed azide-alkyne cycloaddition (CuAAC).

Main Results:

• A fast and efficient method for covalent molecular capsule synthesis via TMA was established.
• Covalent cages were rapidly synthesized using various supramolecular scaffolds.
• A sequential TMA and CuAAC click reaction strategy ('click&click') was successfully developed for complex structures.

Conclusions:

• The TMA reaction is a powerful tool for the efficient synthesis of covalent molecular capsules and cages.
• The developed 'click&click' procedure offers a facile route to intricate molecular architectures.
• This methodology significantly advances the construction of complex systems in supramolecular chemistry.