Synthesis of a Porphyrin-Fused π-Electron System

Bis(bicyclic) molecules dimethanochrysene and diethanochrysene were prepared by Diels‐Alder reaction of the naphthodiyne equivalent with cyclopentadiene and 1,3‐cyclohexadiene, respectively. Reaction of dimethanochrysene and 7,9‐diphenyl‐8H‐cyclopent[a]acenaphthylen‐8‐one resulted in the generation of a fluorescent hydrocarbon in unexpected multistep pericyclic reactions. Syn‐oriented diethanochrysene‐connected bisporphyrin tweezers was prepared from the reaction of chrysene‐bridged syn‐dipyrrole with tripyrranedicarbaldehyde. The structure of the receptor and its 1 : 1 complex with C60 or C70 was determined by X‐ray diffraction analysis. The dihedral angles of the bicyclo[2.2.2]octadiene moieties were narrowed by complexation of the receptor with the fullerenes. The binding affinities of the tweezers with C60 and C70 were calculated to be 2.7(4)×104 and 8.01(7)×104 M−1, respectively by UV‐vis and fluorescence spectroscopy.

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Chrysene‐Bridged Porphyrin Tweezers: Chiral Receptors for Fullerenes

Mori

Kawamoto

Uno

2019

ChemPlusChem

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Synthesis of a Porphyrin-Fused π-Electron System

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References 42 publications

Chrysene‐Bridged Porphyrin Tweezers: Chiral Receptors for Fullerenes

Chrysene‐Bridged Porphyrin Tweezers: Chiral Receptors for Fullerenes

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