Title

Electron Transfer Prompted Ejection of a Tightly Bound K+ from the Ethereal Cavity of a Hexaarylbenzene-Based Receptor

Document Type

Article

Language

eng

Publication Date

2007

Publisher

American Chemical Society

Source Publication

Organic Letters

Source ISSN

1523-7060

Abstract

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.

Comments

Organic Letters, Vol. 9, No. 7 (2007): 1291-1294. DOI.

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