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Updated: Aug 5, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Multi-Macrocyclic Nanohoops Bearing Carbazole-Embedded Cycloparaphenylenes as Geometry-Adaptive Hosts Toward
Wansong Shang1, Li Jin1,2, Yang-Yang Zhang3
1Beijing National Laboratory For Molecular Sciences, CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China.
Abstract:
Curved conjugated molecules with strained non-planar geometries show unique properties valuable for supramolecular chemistry and optoelectronics, but their synthesis and modification remain challenging. We introduce carbazole-embedded cycloparaphenylenes (CPPs) as versatile building blocks to overcome these limitations. Using Suzuki coupling and regioselective bromination, we created a functionalizable macrocyclic synthon. This enabled controlled multi-component couplings to construct trimacrocyclic (TMC) and pentamacrocyclic (PMC) curved π-systems. Structural analyses reveal TMC adopts a well-defined C-shape that self-assembles into tubes, while PMC shows a deformed conformation. Their optical and electronic properties are size-dependent, featuring strong fluorescence and stepwise oxidation to open-shell polycations. Supramolecular studies show TMC acts as an adaptive host, forming distinct 1:1 complexes with C60 (host-guest recognition-induced host cavity expansion) and C70 (encapsulation without conformational change). In comparison, PMC forms 2:1 (guest:host) complexes with C60 or C70. Crystallographic and computational data indicate recognition is governed by the geometrically defined C-shaped cavity rather than the macrocycle's electron-rich nature.
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