Understanding the Chemistry of Strained Alkynes:
At the heart of this research program is the carbon–carbon triple bond, i.e. alkynes, which are versatile structural motifs for a wide range of chemical transformations. Although these reactions represent textbook chemistry which has stood the test of time, the ever increasing efficiency of organic synthetic methods is opening up new avenues for this functional unit. We attempt to harness the intrinsic reactivity of angle-strained alkynes to assemble phenylene scaffolds in a modular manner exploiting macrocyclic ring strain as a driving force for structural transformations. Ultimately, this strategy may provide access to a myriad of fascinating targets: Planar coronoids, twisted molecular architectures, graphitic saddles and curved, flexible π-conjugated nanoribbons and -sheets. Our research is deeply rooted in organic synthesis and the compounds emerging from this program will be subject of interdisciplinary collaborative investigations with the aim to further explore their materials properties and unlock opportunities for future applications. In a broader perspective, strive to develop and apply time and waste-economic synthetic strategies for the preparation of our functional molecular nanocarbons, e.g. transition metal catalyzed cross couplings, olefin metathesis, ‘Click’ reactions, and dynamic covalent chemistry.
Reviving an Old Reaction:
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. 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.