Journal of the American Chemical Society p. 14474 - 14480 (2018)
Update date:2022-08-16
Topics:
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.
Stepień, Marcin
[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.
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