A Macrocycle Based on a Heptagon‐Containing Hexa‐peri‐hexabenzocoronene
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‐mem...
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Veröffentlicht in: | Angewandte Chemie International Edition 2020-08, Vol.59 (35), p.15124-15128 |
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Sprache: | eng |
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Zusammenfassung: | 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.
Carbon nanobasket: A new cyclophane bearing two units of heptagon‐containing hexa‐peri‐hexabenzocoronene is presented. The macrocycle offers an unusual aromatic calix‐shaped cavity able to interact with fullerenes. The selective binding of C70 over C60 is demonstrated. |
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ISSN: | 1433-7851 1521-3773 |
DOI: | 10.1002/anie.202003785 |