Related Experiment Video
Updated: Feb 17, 2026
Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Belt-Shaped [20]Collarene with a Rigid Yet Adaptable Cavity for Multimodal Fullerene Complexation
Yifei Zhang1,2, Ting Liu1,2, Ke Liu3
1State Key Laboratory of Soil Pollution Control and Safety, Stoddart Institute of Molecular Science, Department of Chemistry, Zhejiang University, Hangzhou 310058, P. R. China.
Abstract:
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 [20]collarene and a series of fullerenes. [20]Collarene 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, [20]collarene possesses a shape-adaptable cavity when complexing with two fullerene derivatives, PC61BM and DPC61Py, via different complexation modes. Specifically, [20]collarene 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 [20]collarene 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.
Related Concept Videos
01:23Collar Bearings
01:27¹H NMR: Long-Range Coupling
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
02:02Chair Conformation of Cyclohexane
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
01:20Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
01:16Structure of Conjugated Dienes
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
02:11Conformations of Cyclohexane
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...