Boosting the Host-Guest Binding by Programming the Curvature in Geodesic Nanoribbons

Area of Science:

• Supramolecular Chemistry
• Organic Synthesis
• Materials Science

Background:

• Curvature in aromatic systems is key for self-assembly and host-guest interactions in geodesic polyarenes.
• Synthesizing curved aromatics is challenging, limiting studies on their binding properties.

Purpose of the Study:

• To design and synthesize a polyarene with programmed curvature matching C60.
• To investigate how curvature affects binding affinity and selectivity for fullerenes.

Main Methods:

• Stepwise introduction of five-membered rings to create curved polyarenes.
• Cyclodehydrofluorination as the most effective synthetic route.
• Binding studies with C60 and C70 fullerenes, including experimental and theoretical analyses.

Main Results:

• A novel all-carbon host with C60 curvature was synthesized.
• Curvature tuning dramatically increased binding affinity and selectivity for fullerenes.
• A linear correlation was found between buried surface area and binding energy.
• Selective C70 recognition was achieved through a 2:1 complex with high binding affinity and positive cooperativity.

Conclusions:

• The developed curved polyarenes offer high binding affinities for fullerenes, comparable to macrocyclic hosts.
• Curvature complementarity is crucial for selective fullerene recognition.
• This work provides a foundation for designing geodesic polyarenes and fullerene-based self-assembled materials.