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

26 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

Fingerprint

Hydrocarbons
Benzene
Anions
Chlorides
Negative ions
Methylene Chloride
Dichloromethane
Energy gap
Networks (circuits)

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Majewski, M. A., Hong, Y., Lis, T., Gregoliński, J., Chmielewski, P. J., Cybińska, J., ... 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
Majewski, Marcin A. ; Hong, Yongseok ; Lis, Tadeusz ; Gregoliński, Janusz ; Chmielewski, Piotr J. ; Cybińska, Joanna ; Kim, Dongho ; Stępień, Marcin. / Octulene : A Hyperbolic Molecular Belt that Binds Chloride Anions. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 45. pp. 14072-14076.
@article{7971f33a4cc04c3fa891405d57ecedc0,
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 {\AA} 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.",
author = "Majewski, {Marcin A.} and Yongseok Hong and Tadeusz Lis and Janusz Gregoliński and Chmielewski, {Piotr J.} and Joanna Cybińska and Dongho Kim and Marcin Stępień",
year = "2016",
month = "11",
day = "2",
doi = "10.1002/anie.201608384",
language = "English",
volume = "55",
pages = "14072--14076",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "45",

}

Majewski, MA, Hong, Y, Lis, T, Gregoliński, J, Chmielewski, PJ, Cybińska, J, Kim, D & Stępień, M 2016, 'Octulene: A Hyperbolic Molecular Belt that Binds Chloride Anions', Angewandte Chemie - International Edition, vol. 55, no. 45, pp. 14072-14076. https://doi.org/10.1002/anie.201608384

Octulene : A Hyperbolic Molecular Belt that Binds Chloride Anions. / Majewski, Marcin A.; Hong, Yongseok; Lis, Tadeusz; Gregoliński, Janusz; Chmielewski, Piotr J.; Cybińska, Joanna; Kim, Dongho; Stępień, Marcin.

In: Angewandte Chemie - International Edition, Vol. 55, No. 45, 02.11.2016, p. 14072-14076.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Octulene

T2 - A Hyperbolic Molecular Belt that Binds Chloride Anions

AU - Majewski, Marcin A.

AU - Hong, Yongseok

AU - Lis, Tadeusz

AU - Gregoliński, Janusz

AU - Chmielewski, Piotr J.

AU - Cybińska, Joanna

AU - Kim, Dongho

AU - Stępień, Marcin

PY - 2016/11/2

Y1 - 2016/11/2

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84990848005&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84990848005&partnerID=8YFLogxK

U2 - 10.1002/anie.201608384

DO - 10.1002/anie.201608384

M3 - Article

AN - SCOPUS:84990848005

VL - 55

SP - 14072

EP - 14076

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 45

ER -

Majewski MA, Hong Y, Lis T, Gregoliński J, Chmielewski PJ, Cybińska J et al. Octulene: A Hyperbolic Molecular Belt that Binds Chloride Anions. Angewandte Chemie - International Edition. 2016 Nov 2;55(45):14072-14076. https://doi.org/10.1002/anie.201608384