Efficient immobilization of 9,10-anthraquinonyl moiety at solid interfaces through 2-(bromomethyl)anthraquinone one-electron cleavage

We report here a new and very efficient method for the coverage of different carbon materials with 9,10-anthraquinone attached via a methylene linker. The method is based on one-electron reduction of 2-(bromomethyl)anthraquinone (AQ-CH2-Br) to a free radical AQ–CH2 which was readily achieved using propylene carbonate (PC) as solvent containing tetrabutylammonium iodide. This way, the radical AQ–CH2 adds to the abovementioned carbons forming very stable and dense covalently bound anhraquinonyl methane layers (Г ≈ 2 × 10− 9 mol cm− 2). The grafting could be performed by constant potential electrolyses (q < 0.5 × 10− 3 C mm− 2).

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Facile grafting of 9,10-anthraquinone moiety onto carbon surface. ► Easy generation of 2-methylanthraquinone free radical as key intermediate. ► Dense and chemically stable layers of methyl-anthraquinone on glassy carbon. ► The generation of anthraquinone anion-radical can be governed by the choice of the electrolyte cation.