A Versatile Synthesis of Electroactive Stilbenoprismands for Effective Binding of Metal Cations
American Chemical Society
The Journal of Organic Chemistry
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.
Lindeman, Sergey V.; Rathore, Rajendra; and Debroy, Paromita, "A Versatile Synthesis of Electroactive Stilbenoprismands for Effective Binding of Metal Cations" (2009). Chemistry Faculty Research and Publications. 612.
Accepted version. The Journal of Organic Chemistry, Vol. 74, No. 5 (2009): 2080-2087. DOI. © 2009 American Chemical Society. Used with permission.