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 Stepień

Research output: Contribution to journalArticle

10 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
Pages (from-to)14474-14480
Number of pages7
JournalJournal of the American Chemical Society
Volume140
Issue number43
DOIs
Publication statusPublished - Oct 31 2018

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Fully Conjugated [4]Chrysaorene. Redox-Coupled Anion Binding in a Tetraradicaloid Macrocycle'. Together they form a unique fingerprint.

  • 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., & Stepień, M. (2018). Fully Conjugated [4]Chrysaorene. Redox-Coupled Anion Binding in a Tetraradicaloid Macrocycle. Journal of the American Chemical Society, 140(43), 14474-14480. https://doi.org/10.1021/jacs.8b09385