期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 18, 页码 7421-7427出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b01797
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资金
- National Science Center of Poland [DEC-2015/19/B/ST5/00612]
- MINECO/FEDER of the Spanish Government [CTQ2015-69391-P]
- Ministere de l'Education Nationale, de la Recherche et de la Technologie
- Centre National de la Recherche Scientifique (CNRS)
- Rennes Metropole
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.
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