5 years ago

Stabilizing Fluorine–π Interactions

Stabilizing Fluorine–π Interactions
Josef M. Maier, Mark D. Smith, Christopher J. Yehl, Ken D. Shimizu, Erik C. Vik, Perry J. Pellechia, Ping Li, Brent E. Dial, Amanda E. Rickher
A series of N-arylimide molecular balances were designed to study and measure fluorine–aromatic (F–π) interactions. Fluorine substituents gave rise to increasingly more stabilizing interactions with more electron-deficient aromatic surfaces. The attractive F–π interaction is electrostatically driven and is stronger than other halogen–π interactions. Attractive fluorine: The F–π interaction between a fluorine substituent and an aromatic surface was measured by using a series of molecular balances. This interaction was found to be slightly repulsive with electron-rich surfaces but strongly attractive with electron-poor and cationic surfaces.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702950

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