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Updated: Dec 21, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
A Macrocycle Based on a Heptagon-Containing Hexa-peri-hexabenzocoronene
Vicente G Jiménez1, Arthur H G David1, Juan M Cuerva1
1Departamento de Química Orgánica, Unidad de Excelencia de Química aplicada a Biomedicina y Medio Ambiente, Facultad de Ciencias, Universidad de Granada, Avda. Fuente Nueva, s/n, 18071, Granada, Spain.
Abstract:
A cyclophane is reported incorporating two units of a heptagon-containing extended polycyclic aromatic hydrocarbon (PAH) analogue of the hexa-peri-hexabenzocoronene (HBC) moiety (hept-HBC). This cyclophane represents a new class of macrocyclic structures that incorporate for the first time seven-membered rings within extended PAH frameworks. The saddle curvature of the hept-HBC macrocycle units induced by the presence of the nonhexagonal ring along with the flexible alkyl linkers generate a cavity with shape complementarity and appropriate size to enable π interactions with fullerenes. Therefore, the cyclophane forms host-guest complexes with C60 and C70 with estimated binding constants of Ka =420±2 m-1 and Ka =(6.49±0.23)×103 m-1 , respectively. As a result, the macrocycle can selectively bind C70 in the presence of an excess of a mixture of C60 and C70 .
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