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Inter- and Intramolecular Aryl-Aryl-Interactions in Partially Fluorinated Ethylenedioxy-Bridged Bisarenes

preprint
submitted on 11.07.2020 and posted on 13.07.2020 by Jan-Henrik Weddeling, Yury Vishnevskiy, Beate Neumann, Hans-Georg Stammler, Norbert W. Mitzel
Several ethylenedioxy-bridged bisarenes with a variety of type and number of aryl groups were synthesized to study non-covalent dispersion-driven inter- and intramolecular aryl-aryl-interactions in the solid state and gas phase. Intramolecular interactions are preferably found in the gas phase. DFT calculations of dispersion-corrected energy scans for rotations around the ethylenedioxy-bridge and optimized structures show larger interacting aromatic groups to increase the dispersion energy. Single molecule structures generally adopt folded conformations with short intramolecular aryl-aryl-contacts. Gas electron diffraction experiments were performed exemplarily for 1-(pentafluorophenoxy)-2-(phenoxy)ethane. A new procedure for structure refinement was developed to deal with the conformational complexity of such molecules. The results are an experimental confirmation of the existence of folded conformations of this molecule with short -intramolecular aryl-aryl distances in the gas phase. Solid-state structures are dominated by stretched structures without intramolecular aryl-aryl-interactions but interactions with neighboring molecules

Funding

DFG MI477/28-2

DFG MI477/35-1

DFG VI 713/1-2

History

Email Address of Submitting Author

yury.vishnevskiy@uni-bielefeld.de

Institution

Lehrstuhl für Anorganische Chemie und Strukturchemie, Fakultät für Chemie, Universität Bielefeld

Country

Germany

ORCID For Submitting Author

0000-0002-7130-6280

Declaration of Conflict of Interest

no conflict of interes

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