Gregolinska, Hanna, Majewski, Marcin, Chmielewski, Piotr J., Gregolinski, Janusz, Chien, Alan, Zhou, Jiawang, Wu, Yi-Lin  ORCID: https://orcid.org/0000-0003-0253-1625, Bae, Youn Jue, Wasielewski, Michael R., Zimmerman, Paul M. and Stepien, Marcin
2018.
Fully conjugated [4] chrysaorene. Redox-coupled anion binding in a tetraradicaloid macrocycle.
Journal of the American Chemical Society
140
(43)
, pp. 14474-14480.
10.1021/jacs.8b09385
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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.
| Item Type: | Article |
|---|---|
| Date Type: | Publication |
| Status: | Published |
| Schools: | Schools > Chemistry |
| Publisher: | American Chemical Society |
| ISSN: | 0002-7863 |
| Date of First Compliant Deposit: | 31 July 2019 |
| Date of Acceptance: | 5 October 2018 |
| Last Modified: | 17 Jul 2025 21:45 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/124621 |
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