Electro-mechanically switchable hydrocarbons based on [8]annulenes.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 35165264.
- Also identified by DOI 10.1038/s41467-022-28384-8 and PMC identifier 8844043.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
Abstract
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) π-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.