Title

A Versatile Synthesis of Electroactive Stilbenoprismands for Effective Binding of Metal Cations

Document Type

Article

Language

eng

Publication Date

2009

Publisher

American Chemical Society

Source Publication

The Journal of Organic Chemistry

Source ISSN

0022-3263

Abstract

A versatile synthesis of a new class of polyaromatic receptors (stilbenoprismands) containing a Δ-shaped cavity similar to that of the π-prismand together with an intimately coupled electroactive stilbenoid moiety was accomplished via an efficient intramolecular McMurry coupling reaction. The presence of the Δ-shaped cavity in stilbenoprismands allows an efficient binding of a single silver cation as probed by 1H NMR spectroscopy. Electron-rich stilbenoprismands undergo a ready oxidation to their highly robust cation−radical and dicationic salts. X-ray structure determination of a representative dicationic stilbenoprismand showed that the charges were largely localized on the tetraarylethylene moiety, which results in a twisting of the ethylenic C═C bond by ∼35°. Moreover, the electronic coupling among the stilbenoid and π-prismand moieties in various stilbenoprismands was briefly probed by optical methods.

Comments

The Journal of Organic Chemistry, Vol. 74, No. 5 (2009): 2080-2087. DOI.

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