Unsubstituted Bambusurils: Post-Macrocyclization Modification of Versatile Intermediates.

Area of Science:

• Supramolecular Chemistry
• Organic Synthesis

Background:

• Bambusurils are macrocyclic compounds with potential applications in molecular recognition and host-guest chemistry.
• Functionalization of macrocycles is key to tailoring their properties for specific applications.

Purpose of the Study:

• To isolate and characterize a new bambusuril derivative, (H)BU[6], lacking substituents on its ureidic nitrogen atoms.
• To demonstrate the utility of (H)BU[6] as a precursor for synthesizing other bambusuril derivatives.

Main Methods:

• Deprotection of the precursor (PMB)BU[6] to yield (H)BU[6].
• Characterization of the isolated (H)BU[6] macrocycle.
• Functionalization of (H)BU[6] via propargylation.
• Copper-catalyzed click reaction on the propargylated macrocycle.

Main Results:

• Successful isolation and full characterization of the new bambusuril derivative (H)BU[6].
• Demonstration of facile propargylation of (H)BU[6].
• Successful application of the copper-catalyzed click reaction to the functionalized macrocycle, showcasing its synthetic versatility.

Conclusions:

• The newly synthesized (H)BU[6] is a valuable and accessible building block for diverse bambusuril derivatives.
• The synthetic route highlights the potential for creating complex functionalized macrocycles from simple precursors.
• (H)BU[6] opens new avenues for developing tailored bambusuril-based materials and systems.