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Chrysene‐Bridged Porphyrin Tweezers: Chiral Receptors for Fullerenes
Author(s) -
Mori Shigeki,
Kawamoto Naoki,
Uno Hidemitsu
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201900046
Subject(s) - chrysene , porphyrin , fullerene , molecular tweezers , chemistry , tweezers , nanotechnology , supramolecular chemistry , materials science , photochemistry , organic chemistry , molecule , pyrene
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‐8 H ‐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 C 60 or C 70 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 C 60 and C 70 were calculated to be 2.7(4)×10 4 and 8.01(7)×10 4 M −1 , respectively by UV‐vis and fluorescence spectroscopy.