Octulene: A Hyperbolic Molecular Belt that Binds Chloride Anions

Marcin A. Majewski, Yongseok Hong, Tadeusz Lis, Janusz Gregoliński, Piotr J. Chmielewski, Joanna Cybińska, Dongho Kim, Marcin Stępień

Research output: Contribution to journalArticle

27 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)14072-14076
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number45
DOIs
Publication statusPublished - 2016 Nov 2

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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    Majewski, M. A., Hong, Y., Lis, T., Gregoliński, J., Chmielewski, P. J., Cybińska, J., Kim, D., & Stępień, M. (2016). Octulene: A Hyperbolic Molecular Belt that Binds Chloride Anions. Angewandte Chemie - International Edition, 55(45), 14072-14076. https://doi.org/10.1002/anie.201608384