Molecular spoked wheels with an all-phenylene backbone and different alkoxy side chain substitution patterns were synthesized using a cobalt-catalyzed [2 + 2 + 2] cycloaddition and subsequent template-directed cyclization via Yamamoto coupling. The two-dimensional organization of the molecules at the solid/liquid interface was investigated by means of scanning tunneling microscopy, allowing imaging of the molecular structure with submolecular resolution. With the right proportion of the flexible alkyl corona to the rigid core, mesomorphic behavior of one compound could be observed over a wide temperature range.

Organic electrode materials for rechargeable batteries are becoming a viable alternative for existing technologies. In particular, redox polymers have shown great performances. While many cathode‐active derivatives are known, the development of their anode‐active counterparts, required for the design of full‐organic batteries, lacks behind. Here we present investigation on the suitability of cyclooctatetraene (COT)‐based aliphatic polymers as anode‐active battery materials, inspired by the known reversible reduction chemistry of COT at low electrochemical potential. We found that both synthesized polystyrene derivatives, side‐group functionalized with COT, showed limited electrochemical reversibility of the reduction processes, whereas reductions proceeded reversibly in model compounds of these polymers. Differential scanning calorimetry measurements and density‐functional theory calculations showed that this incomplete reversibility was due to cross‐linking reactions occurring between COT units in the polymers. For the future of COT‐based redox polymers, we propose a molecular design that prevents these cross‐linking reactions.

Molecular spoked wheels with D3h and Cs symmetry are synthesized by Vollhardt trimerization of C2v-symmetric dumbbell structures with central acetylene units and subsequent intramolecular ring closure. Scanning tunneling microscopy of the D3h-symmetric species at the solid/liquid...

All-phenylene molecular spoked wheels, cutouts of graphenylene-3, have been synthesized by intramolecular Yamamoto coupling of the respective dodecabromides. The uneven number of aromatics at the sides of the wheels requires...

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