Tasić Magdalena, Ivković Jakov, Carlström Göran, Melcher Michaela, Bollella Paolo, Bendix Jesper, Gorton Lo, Persson Petter, Uhlig Jens, Strand Daniel
Centre for Analysis and Synthesis, Department of Chemistry, Lund University, Box 124, SE-221 00, Lund, Sweden.
Department of Analytical Chemistry/Biochemistry, Lund University, Box 124, SE-221 00, Lund, Sweden.
Nat Commun. 2022 Feb 14;13(1):860. doi: 10.1038/s41467-022-28384-8.
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.
