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Lemniscular [16]cycloparaphenylene: a radially conjugated figure-eight aromatic molecule.
Autorzy
Rok wydania
2019
Czasopismo
Journal of the American Chemical Society
Numer woluminu
141
Strony
7421-7427
DOI
10.1021/jacs.9b01797
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
A cycloparaphenylene-based molecular lemniscate (CPPL) was obtained in a short synthesis involving masked p-phenylene equivalents. The strained figure-eight geometry of CPPL is sustained by the incorporated 9,9′-bicarbazole subunit, which also acts as a stereogenic element. The shape of the distorted [16]cycloparaphenylene nanohoop embedded in CPPL is accurately approximated with a Booth lemniscate. The structure of CPPL, investigated using NMR and Raman spectroscopic methods, revealed strain-dependent features, consistent with the variable curvature of the ring. The electronic and optical properties of CPPL combine features more characteristic of smaller cycloparaphenylenes, such as a reduced optical bandgap and red-shifted fluorescence. CPPL was resolved into enantiomers, which are configurationally stable and provide strong chiroptical responses, including circularly polarized luminescence.
Adres publiczny
http://dx.doi.org/10.1021/jacs.9b01797