Chrysene‐Bridged Porphyrin Tweezers: Chiral Receptors for Fullerenes

Abstract

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.

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

“…In 2019, Uno et al prepared 1,5-naphthodiyne equivalent 15-86 and subjected it to the Diels–Alder reactions with cyclopentadiene and 1,3-cyclohexadiene, obtaining cycloadducts 15-87 and 15-88 , respectively (Scheme b) . Both reactions resulted in 1:1 mixtures of syn - and anti -isomers.…”