Fully Conjugated [4]Chrysaorene. Redox-Coupled Anion Binding in a Tetraradicaloid Macrocycle

Hanna Gregolińska, Marcin Majewski, Piotr J. Chmielewski, Janusz Gregoliński, Alan Chien, Jiawang Zhou, Yi Lin Wu, Youn Jue Bae, Michael R Wasielewski, Paul M. Zimmerman, Marcin Stȩpień

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

[4]Chrysaorene, a fully conjugated carbocyclic coronoid, is shown to be a low-bandgap π-conjugated system with a distinct open-shell character. The system shows good chemical stability and can be oxidized to well-defined radical cation and dication states. The cavity of [4]chrysaorene acts as an anion receptor toward halide ions with a particular selectivity toward iodides (Ka = 207 ± 6 M-1). The interplay between anion binding and redox chemistry is demonstrated using a 1H NMR analysis in solution. In particular, a well-resolved, paramagnetically shifted spectrum of the [4]chrysaorene radical cation is observed, providing evidence for the inner binding of the iodide. The radical cation-iodide adduct can be generated in thin solid films of [4] chrysaorene by simple exposure to diiodine vapor.

Original languageEnglish
JournalJournal of the American Chemical Society
DOIs
Publication statusAccepted/In press - Jan 1 2018

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Iodides
Oxidation-Reduction
Anions
Cations
Negative ions
Positive ions
Chemical stability
Energy gap
Vapors
Nuclear magnetic resonance
Ions

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Gregolińska, H., Majewski, M., Chmielewski, P. J., Gregoliński, J., Chien, A., Zhou, J., ... Stȩpień, M. (Accepted/In press). Fully Conjugated [4]Chrysaorene. Redox-Coupled Anion Binding in a Tetraradicaloid Macrocycle. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.8b09385

Fully Conjugated [4]Chrysaorene. Redox-Coupled Anion Binding in a Tetraradicaloid Macrocycle. / Gregolińska, Hanna; Majewski, Marcin; Chmielewski, Piotr J.; Gregoliński, Janusz; Chien, Alan; Zhou, Jiawang; Wu, Yi Lin; Bae, Youn Jue; Wasielewski, Michael R; Zimmerman, Paul M.; Stȩpień, Marcin.

In: Journal of the American Chemical Society, 01.01.2018.

Research output: Contribution to journalArticle

Gregolińska, H, Majewski, M, Chmielewski, PJ, Gregoliński, J, Chien, A, Zhou, J, Wu, YL, Bae, YJ, Wasielewski, MR, Zimmerman, PM & Stȩpień, M 2018, 'Fully Conjugated [4]Chrysaorene. Redox-Coupled Anion Binding in a Tetraradicaloid Macrocycle', Journal of the American Chemical Society. https://doi.org/10.1021/jacs.8b09385
Gregolińska, Hanna ; Majewski, Marcin ; Chmielewski, Piotr J. ; Gregoliński, Janusz ; Chien, Alan ; Zhou, Jiawang ; Wu, Yi Lin ; Bae, Youn Jue ; Wasielewski, Michael R ; Zimmerman, Paul M. ; Stȩpień, Marcin. / Fully Conjugated [4]Chrysaorene. Redox-Coupled Anion Binding in a Tetraradicaloid Macrocycle. In: Journal of the American Chemical Society. 2018.
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