Aromatic Nanosandwich Obtained by σ-Dimerization of a Nanographenoid π-Radical

Moshniaha L, Żyła-Karwowska M, Chmielewski PJ, Lis T, Cybińska J, Gońka E, Oschwald J, Drewello T, Rivero SM, Casado J, Stȩpień M (2020)

Publication Type: Journal article

Publication year: 2020

Journal

Journal of the American Chemical Society American Chemical Society

Book Volume: 142

Pages Range: 3626-3635

Journal Issue: 7

DOI: 10.1021/jacs.9b13942

Abstract

A 139-π-electron nanographenoid radical was obtained by expanding the periphery of a naphthalimide-azacoronene hybrid with a methine bridge. The radical was isolated in the form of its σ-dimer, which was shown to possess a conformationally restricted two-layer structure both in the solid state and in solution. The dimer is cleaved into its parent radicals when exposed to ultraviolet or visible radiation in toluene solutions but is resistant to thermally induced dissociation. Under inert conditions, the radicals recombine quantitatively into the σ-dimer with observable kinetics, but they are oxidized into a ketone derivative in the presence of atmospheric oxygen. Combined structural, spectroscopic, and theoretical evidence shows that the σ-dimer contains a weak C(sp3)-C(sp3) bond, but is stabilized against thermal dissociation by a very strong dispersive interaction between the overlapping πsurfaces.

Authors with CRIS profile

Johannes Oschwald Professur für Physikalische Chemie Thomas Drewello Professur für Physikalische Chemie

Involved external institutions

University of Wroclaw / Uniwersytet Wrocławski PL Poland (PL) Universidad de Málaga / University of Malaga ES Spain (ES)

How to cite

APA:

Moshniaha, L., Żyła-Karwowska, M., Chmielewski, P.J., Lis, T., Cybińska, J., Gońka, E.,... Stȩpień, M. (2020). Aromatic Nanosandwich Obtained by σ-Dimerization of a Nanographenoid π-Radical. Journal of the American Chemical Society, 142(7), 3626-3635. https://doi.org/10.1021/jacs.9b13942

MLA:

Moshniaha, Liliia, et al. "Aromatic Nanosandwich Obtained by σ-Dimerization of a Nanographenoid π-Radical." Journal of the American Chemical Society 142.7 (2020): 3626-3635.

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