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Fully Conjugated [4]Chrysaorene. Redox-Coupled Anion Binding in a Tetraradicaloid Macrocycle
- Source :
- Journal of the American Chemical Society. 140(43)
- Publication Year :
- 2018
-
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.
- Subjects :
- chemistry.chemical_classification
010405 organic chemistry
Chemistry
Iodide
General Chemistry
Conjugated system
010402 general chemistry
Photochemistry
01 natural sciences
Biochemistry
Redox
Catalysis
0104 chemical sciences
Adduct
Dication
Colloid and Surface Chemistry
Radical ion
Chemical stability
Anion binding
Subjects
Details
- ISSN :
- 15205126 and 00027863
- Volume :
- 140
- Issue :
- 43
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi.dedup.....6e3e7e69a2fd884a0c673e25270c0cb5