Electro-mechanically switchable hydrocarbons based on [8]annulenes

Pure hydrocarbons with shape and conjugation properties that can be switched by external stimuli is an intriguing prospect in the design of new responsive materials and single-molecule electronics. Here, we develop an oligomeric [8]annulene-based material that combines a remarkably efficient topological switching upon redox changes with structural simplicity, stability, and straightforward synthesis: 5,12-alkyne linked dibenzo[a,e]cyclooctatetraenes (dbCOTs). Upon reduction, the structures accommodate a reversible reorganization from a pseudo-conjugated tub-shape to a conjugated aromatic system. This switching in oligomeric structures gives rise to multiple defined states that are deconvoluted by electrochemical, NMR, and optical methods. The combination of stable electromechanical responsivity and ability to relay electrons stepwise through an extended (pseudo-conjugated) pi-system in partially reduced structures validate alkyne linked dbCOTs as a practical platform for developing new responsive materials and switches based on [8]annulene cores.

Automated summary

This study presents a material based on oligomeric [8]annulene that can efficiently switch its shape upon redox changes. The material has a simple structure, stability, and can be easily synthesized. The switching in the oligomeric structures leads to multiple defined states, which can be characterized using electrochemical, NMR, and optical methods. The material shows stable electromechanical responsivity and the ability to relay electrons stepwise through a (pseudo-conjugated) pi-system in partially reduced structures, making it a practical platform for developing new responsive materials and switches based on [8]annulene cores.