A Three-Dimensional Capsule-like Carbon Nanocage as a Segment Model of Capped Zigzag [12,0] Carbon Nanotubes: Synthesis, Characterization, and Complexation with C70

Article abstract of DOI:10.1002/anie.201804031

Herein we report the synthesis and photophysical and supramolecular properties of a novel three-dimensional capsule-like hexa-peri-hexabenzocoronene (HBC)-containing carbon nanocage, tripodal-[2]HBC, which is the first synthetic model of capped zigzag [12,0] carbon nanotubes (CNTs). Tripodal-[2]HBC was synthesized by the palladium-catalyzed coupling of triboryl hexabenzocoronene and L-shaped cyclohexane units, followed by nickel-mediated C?Br/C?Br coupling and subsequent aromatization of the cyclohexane moieties. The physical properties of tripodal-[2]HBC and its supramolecular host–guest interaction with C₇₀ were further studied by UV/Vis and fluorescence spectroscopy. Theoretical calculations revealed that the strain energy of tripodal-[2]HBC was as high as 55.2 kcal mol^?1.