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Updated: Sep 16, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
A Self-Cyclocondensation Approach for the Synthesis of a Cycloparaphenylene-End-Capped Molecular Cylinder
Zhuofan Xu1, Xingchi Liu1, Chang Ge1
1Institute of Molecular Plus, Tianjin University and Haihe Laboratory of Sustainable Chemical Transformations, 92 Weijin Road, Tianjin 300072, P. R. China.
Abstract:
The synthesis of molecular cylinders is challenging due to their intrinsic strain and the complexity of the structure. Here we report an efficient self-cyclocondensation approach for the construction of molecular cylinder MC3, taking advantage of a cycloparaphenylene precursor comprising both diamine and diketone moieties within the macrocyclic skeleton. The tilted cylindrical geometry of MC3 was revealed by X-ray single crystal analysis, and variable temperature NMR analysis suggested a dynamic time-averaged structure in the solution phase. MC3 exhibits distinct optical properties, including solvatofluorochromism and a moderate fluorescence quantum yield, associated with the CT characteristics of the excited state. The building block in this study may be further employed for the construction of polymeric structures and fully fused cylindrical structures.
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