Chloroanthraquinone as a grafted probe molecule to investigate grafting yield on carbon powder

Spontaneous grafting of chloroanthraquinone (ClAQ) groups on Black Pearls carbon by reduction of the corresponding in-situ generated diazonium cations was successfully achieved. The presence of an halogen atom on the quinone molecule allowed the use of different spectroscopic characterization techniques to determine the accurate quinone content of the modified carbon. Electrochemical characterization highlighted that the presence of chlorine atom on the grafted molecule did not affect the electrochemical response or the grafting reaction efficiency. The amount of ClAQ molecules at the carbon surface after grafting was determined by cyclic voltammetry, together with thermogravimetric analysis coupled mass spectroscopy, X-ray photoelectron spectroscopy and elemental analysis. The ClAQ mass loadings estimated from the four techniques are in very good agreement and confirm that the grafted moieties are all electrochemically active and accessible. Finally, the grafting of quinone-type molecule using the reduction of diazonium cations does not affect the electroactivity of the grafted groups and cyclic voltammetry can be considered as a reliable technique to evaluate the mass loading of grafted quinone groups on porous carbon. Thus ClAQ can be used as a grafted probe molecule to investigate grafting yield on carbon powder, and this approach can be extended to functionalized electrodes used in an increasing number of electrochemical energy storage devices.