title: Octulene: A Hyperbolic Molecular Belt that Binds Chloride Anions.
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)×104m-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.
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland.
authors.forename: Marcin A
authors.initials: MA
authors.lastname: Majewski
authors.affiliation: Department of Chemistry, Yonsei University, 50 Yonsei-ro, Seoul, 120-749, Korea.
authors.forename: Yongseok
authors.initials: Y
authors.lastname: Hong
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland.
authors.forename: Tadeusz
authors.initials: T
authors.lastname: Lis
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland.
authors.forename: Janusz
authors.initials: J
authors.lastname: Gregoliński
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland.
authors.forename: Piotr J
authors.initials: PJ
authors.lastname: Chmielewski
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland.
authors.forename: Joanna
authors.initials: J
authors.lastname: Cybińska
authors.affiliation: Department of Chemistry, Yonsei University, 50 Yonsei-ro, Seoul, 120-749, Korea. dongho@yonsei.ac.kr.
authors.forename: Dongho
authors.initials: D
authors.lastname: Kim
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland. marcin.stepien@chem.uni.wroc.pl.
authors.forename: Marcin
authors.initials: M
authors.lastname: Stępień
keywords: anion binding; aromaticity; hydrocarbons; organic synthesis; photophysics