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Angew Chem Int Ed Engl. 2017 Oct 16;56(43):13259-13263. doi: 10.1002/anie.201707716. Epub 2017 Sep 19.

Intramolecular π-π Interactions in Flexibly Linked Partially Fluorinated Bisarenes in the Gas Phase.

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Lehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2, Fakultät für Chemie, Universität Bielefeld, Universitätsstrasse 25, 33615, Bielefeld, Germany.


Three compounds with phenyl and pentafluorophenyl rings bridged by (CH2 )3 and (CH2 )2 SiMe2 units were synthesized by hydrosilylation and C-C coupling reactions. Their solid-state structures are dominated by intermolecular π stacking interactions, primarily leading to dimeric or chain-type aggregates. Analysis of free molecules in the gas phase by electron diffraction revealed the most abundant conformer to be significantly stabilized by intramolecular π-π interactions. For the silicon compounds, structures characterized by σ-π interactions between methyl and pentafluorophenyl groups are second lowest in energy and cannot be excluded completely by the gas electron diffraction experiments. C6 H5 (CH2 )3 C6 F5 , in contrast, is present as a single conformer. The gas-phase structures served as a reference for the evaluation of a series of (dispersion-corrected) quantum-chemical calculations.


bridged arenes; dispersion interactions; gas electron diffraction; intermolecular π stacking; intramolecular π stacking


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