We report an anti-folded bowl-shaped bisdibenzocorannulene (BDBC)f eaturing an ew chair-cyclohexane-like hexagon as abridge of two dibenzocorannulene moieties.The neutral compound showed multiple redox-active properties and could be converted to the corresponding redox states through chemical reduction or oxidation.C hemical reduction of BDBC by stoichiometric addition of metallic potassium in the presence of [18]crown-6 ether,p rovided ar adical anion BDBCC À and adianion BDBC 2À ,respectively;while chemical oxidation by silver hexafluoroantimonate(V), converted the neutral compound to an open-shell singlet diradical dication (BDBCCC) 2+ .T he structural consequences of both electronreduction and oxidation were closely related to the release of ring-strain of the bowl-shaped p-scaffold and imposed steric hindrance of the hexagonal bridge.I na ddition, the unusual open-shell nature of the dication could mainly be attributed to the changing of localized antiaromaticity in the closed-shell structure to delocalized character in the biradical, and thus the emergence of weakly bonded p-electrons.
We report an anti‐folded bowl‐shaped bisdibenzocorannulene (BDBC) featuring a new chair‐cyclohexane‐like hexagon as a bridge of two dibenzocorannulene moieties. The neutral compound showed multiple redox‐active properties and could be converted to the corresponding redox states through chemical reduction or oxidation. Chemical reduction of BDBC by stoichiometric addition of metallic potassium in the presence of [18]crown‐6 ether, provided a radical anion BDBC.− and a dianion BDBC2−, respectively; while chemical oxidation by silver hexafluoroantimonate(V), converted the neutral compound to an open‐shell singlet diradical dication (BDBC..)2+. The structural consequences of both electron‐reduction and oxidation were closely related to the release of ring‐strain of the bowl‐shaped π‐scaffold and imposed steric hindrance of the hexagonal bridge. In addition, the unusual open‐shell nature of the dication could mainly be attributed to the changing of localized antiaromaticity in the closed‐shell structure to delocalized character in the biradical, and thus the emergence of weakly bonded π‐electrons.
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