Benzoin Condensation: Reviving an Old Reaction for New Anode Materials in Organic Batteries

Taking into account their manifold benefits, organic batteries are forecast to replace the currently established lithium-ion technology based on inorganic materials in near future. To meet the expectations associated with this technology, various parameters can be fine-tuned by device engineering, though ultimately, the most integral component is represented by the active materials used. At the bottom line, an ideal organic material would be a highly redox stable, comprises a maximum number of functional units per mass, and can be prepared via cost effective and environmentally benign methods. Our vision is that carbonyl-containing molecules and polymers prepared via Benzoin condensation can deliver such next generation anode materials. On the way to this ultimate target, the most important challenges will be addressed in this proof-of-principle study. Beyond this background, the Schaub group (functional molecular materials) and the Scheiba group (carbon-based materials for electrochemical energy storage) join forces to systematically explore this new avenue. Specifically, starting from readily available polyaldehyde precursors, an efficient access to redox active 1,2-diketone containing macrocycles and polymers will be disclosed and the ad hoc prepared materials tested as anodes in organic batteries. With this approach we not only strive to revive an old, yet conceptually simple and appealing class of redox active materials, but also develop an economically efficient and environmentally benign synthetic route for their preparation.