Collarenes, in which alternating benzenoid and 1,4-cyclohexadiene rings are fused to form belt-shaped hydrocarbons, show exceptional promise as molecular containers in supramolecular chemistry. However, the experimental investigation of their host-guest chemistry remains largely untapped. Herein, we report multimodal complexation behaviors between 20collarene and a series of fullerenes. 20Collarene is capable of complexing both C60 and C70 to form inclusion complexes, as confirmed by proton nuclear magnetic resonance spectroscopy, isothermal titration calorimetry, high-resolution mass spectrometry, and single-crystal X-ray crystallography. The strong binding affinities for fullerenes (Ka up to 105 M-1) lead to host-guest complexes that display ultrafast charge separation and a stable charge-separated state. Moreover, 20collarene possesses a shape-adaptable cavity when complexing with two fullerene derivatives, PC61BM and DPC61Py, via different complexation modes. Specifically, 20collarene exhibits fully encapsulated host-guest complexation with PC61BM, whereas it engages in solvent-synergistic complexation with DPC61Py. This work systematically establishes the host-guest chemistry of 20collarene with a rigid yet adaptive cavity, thereby laying a crucial foundation in the field of collarene-based supramolecular chemistry and guiding its future development toward functional materials.
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