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Complexation of an Anthracene‐Triptycene Nanocage Host with Fullerene Guests through CH⋅⋅⋅π Contacts
Author(s) -
Kajiyama Kazuki,
Tsurumaki Eiji,
Wakamatsu Kan,
Fukuhara Gaku,
Toyota Shinji
Publication year - 2021
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000816
Subject(s) - triptycene , anthracene , fullerene , chemistry , host–guest chemistry , selectivity , toluene , molecule , hydrocarbon , titration , fluorescence , inclusion compound , photochemistry , crystallography , polymer chemistry , supramolecular chemistry , organic chemistry , physics , quantum mechanics , catalysis
Abstract A bicyclic anthracene macrocycle containing two triptycene units at the bridgehead positions was synthesized by Ni‐mediated coupling of the corresponding precursor as a cage‐shaped aromatic hydrocarbon host. This cage host formed an inclusion complex with C 60 or C 70 guest in 1 : 1 ratio in solution. The association constants ( K a ) determined by the fluorescence titration method were 1.3×10 4 and 3.3×10 5 L mol −1 for the C 60 and C 70 complexes, respectively, at 298 K in toluene. DFT calculations revealed that the guest molecules were included in the middle of the cavity with several CH⋅⋅⋅π contacts. The strong affinity of the cage host for the fullerene guests and the high selectivity toward C 70 are discussed on the basis of spectroscopic and structural data.