Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes

Marvin Linnemannstöns; Beate Neumann; Hans-Georg Stammler; Norbert W. Mitzel

doi:10.1055/s-0039-1690785

Synthesis, Table of Contents

Synthesis 2020; 52(07): 1025-1034
DOI: 10.1055/s-0039-1690785

paper

Synthesis and Structural Diversity of Triaryl(phenylethyl)silanes

Marvin Linnemannstöns

,

Beate Neumann

,

Hans-Georg Stammler

,

Norbert W. Mitzel∗

Universität Bielefeld, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie und Strukturchemie, Universitätsstraße 25, 33615 Bielefeld, Germany Email: mitzel@uni-bielefeld.de

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Abstract

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Abstract

Starting from trichloro(phenylethyl)silane, six differently fluorinated triaryl(phenylethyl)silanes were synthesized by salt elimination reactions and their structures were determined by X-ray diffraction analysis. Tris(pentafluorophenyl)(phenylethyl)silane reveals a folded structure due to intramolecular π-stacking interactions, while those with a lower degree of fluorination show either intermolecular π-stacking or no interplay between the aryl groups. A similar folded structure was observed for (4-methylphenethyl)tris(pentafluorophenyl)silane and [2-(naphth-2-yl)ethyl]tris(pentafluorophenyl)silane, both generated from the corresponding trichlorosilanes. In contrast, the inversely fluorinated [2-(pentafluorophenyl)ethyl]triphenylsilane only revealed intermolecular π-stacking interactions. Compounds with tetrafluoropyridyl substituents behave differently; with these compounds, π-stacking is only observed between the fluorinated units. All compounds were analyzed by NMR and IR spectroscopy, elemental analyses and single-crystal X-ray diffraction, and found to have strong H/C/N/F···F and N···C contacts.

Key words

inter/intramolecular π-stacking - solid-state structures - London dispersion - bridged arenes - fluorinated arenes

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References

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