A Macrocycle Based on a Heptagon-Containing Hexa-peri-hexabenzocoronene.

Angew Chem Int Ed Engl

Departamento 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.

Published: August 2020

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 C and C with estimated binding constants of K =420±2 m and K =(6.49±0.23)×10  m , respectively. As a result, the macrocycle can selectively bind C in the presence of an excess of a mixture of C and C .

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http://dx.doi.org/10.1002/anie.202003785DOI Listing

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