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

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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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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., Wu, Y. L., Bae, Y. J., Wasielewski, M. R., Zimmerman, P. M., & 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