A Macrocycle Based on a Heptagon-Containing Hexa-peri-hexabenzocoronene
Vicente G. Jiménez
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
Search for more papers by this authorArthur H. G. David
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
Search for more papers by this authorProf. Juan M. Cuerva
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
Search for more papers by this authorCorresponding Author
Dr. Victor Blanco
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
Search for more papers by this authorCorresponding Author
Dr. Araceli G. Campaña
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
Search for more papers by this authorVicente G. Jiménez
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
Search for more papers by this authorArthur H. G. David
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
Search for more papers by this authorProf. Juan M. Cuerva
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
Search for more papers by this authorCorresponding Author
Dr. Victor Blanco
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
Search for more papers by this authorCorresponding Author
Dr. Araceli G. Campaña
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
Search for more papers by this authorAbstract
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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