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

Article abstract of DOI:10.1021/jacs.8b09385

[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 (K_a = 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.

Full text of DOI:10.1021/jacs.8b09385

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Article
Fully Conjugated [4]Chrysaorene. Redox-Coupled
Anion Binding in a Tetraradicaloid Macrocycle
Hanna Gregoli#ska, Marcin Majewski, Piotr J. Chmielewski, Janusz Gregoli#ski, Alan Chien, Jiawang
Zhou, Yi-Lin Wu, Youn Jue Bae, Michael R. Wasielewski, Paul M. Zimmerman, and Marcin St#pie#
J. Am. Chem. Soc., Just Accepted Manuscript • DOI: 10.1021/jacs.8b09385 • Publication Date (Web): 05 Oct 2018
Downloaded from http://pubs.acs.org on October 5, 2018
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