American Chemical Society
Synthesis of a pair of rotamers (9u/9s) of a hexaarylbenzene derivative containing six (cofacially arranged) electroactive 2,5-dimethoxytolyl groups is described. The toroidal electronic stabilization due to the circular arrangement of aryl groups in 9u/9s leads to the observation of multiple (reversible) oxidation waves and lowering of their Eox1 by ∼250 mV relative to model compounds. The binding of K+ to symmetrical rotamer 9s was monitored by an electrochemical method and further confirmed by X-ray crystallography.
Shukla, Ruchi; Lindeman, Sergey V.; and Rathore, Rajendra, "Electron Transfer Prompted Ejection of a Tightly Bound K+ from the Ethereal Cavity of a Hexaarylbenzene-Based Receptor" (2007). Chemistry Faculty Research and Publications. 632.