Synthesis of Calix

Area of Science:

• Supramolecular Chemistry
• Organic Synthesis
• Crystal Engineering

Background:

• Calix[4]arene derivatives are versatile macrocyclic hosts.
• Triflates of calix[4]arenes are key intermediates in organic synthesis.
• Palladium-catalyzed reactions offer efficient synthetic routes.

Purpose of the Study:

• To synthesize and characterize various p-tert-butylcalix[4]arene triflates.
• To investigate the reactivity of these triflates under palladium-catalyzed conditions.
• To explore the formation and structural characterization of novel clathrate complexes.

Main Methods:

• Synthesis of p-tert-butylcalix[4]arene mono-, bis-, tris-, and tetrakistriflates.
• Palladium-catalyzed carbonylative coupling reactions.
• Suzuki-Miyaura coupling and deoxygenation reactions.
• X-ray crystallography for structural determination.

Main Results:

• Formation of p-tert-butylcalix[4]arene triflates (3, 2, 4, 5) achieved.
• A novel 1:1 clathrate (6) of benzophenone and calixarene derivative 3 was synthesized.
• The first nonsolvent-derived clathrate of a calix[4]arene derivative was structurally characterized by X-ray crystallography.
• A triethylamine clathrate with 3 was observed during deoxygenation.

Conclusions:

• The study successfully synthesized and characterized novel calixarene triflates.
• The formation and structural elucidation of a unique nonsolvent-derived benzophenone clathrate demonstrate new supramolecular assembly possibilities.
• Palladium-catalyzed reactions provide effective pathways for functionalizing calix[4]arenes and forming inclusion complexes.