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Inne
Octulene: a hyperbolic molecular belt that binds chloride anions.
Autorzy
Rok wydania
2016
Czasopismo
Angewandte Chemie - International Edition
Numer woluminu
55
Strony
14072-14076
DOI
10.1002/anie.201608384
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
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.
Słowa kluczowe
anion binding, aromaticity, hydrocarbons, organic synthesis, photophysics
Adres publiczny
http://dx.doi.org/10.1002/anie.201608384
Strona internetowa wydawcy
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