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- Title
Octulene: A Hyperbolic Molecular Belt that Binds Chloride Anions.
- Authors
Majewski, Marcin A.; Hong, Yongseok; Lis, Tadeusz; Gregoliński, Janusz; Chmielewski, Piotr J.; Cybińska, Joanna; Kim, Dongho; Stępień, Marcin
- Abstract
Octulene, the higher homologue of kekulene and septulene, was synthesized using the fold-in method. This new hydrocarbon macrocycle contains a large 24-membered inner circuit, which is peripherally fused to 24 benzene rings. Such an arrangement produces considerable hyperbolic distortion of the π-conjugated surface. The consequences of distortion in octulene were explored using photophysical methods, which revealed a reduced electronic band gap and greater flexibility of the π system. Octulene contains a functional cavity with a diameter larger than 5.5 Å that is capable of efficiently binding the chloride anion in a nonpolar solvent ( Ka= 2.2(4)×104 m−1, 1 % dichloromethane (DCM) in benzene). The octulene-chloride interaction is stabilized by eight weak C(sp2)H⋅⋅⋅Cl bonds, providing the first example of a hydrocarbon-based anion receptor.
- Subjects
HYDROCARBON synthesis; ANIONS; CHLORIDES; MACROCYCLIC compound synthesis; BENZENE; DICHLOROMETHANE
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 45, p14278
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201608384