Electro-mechanically switchable hydrocarbons based on [8]annulenes

Magdalena Tasić, Jakov Ivković, Göran Carlström, Michaela Melcher, Paolo Bollella, Jesper Bendix, Lo Gorton, Petter Persson, Jens Uhlig and Daniel Strand ()
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Magdalena Tasić: Lund University
Jakov Ivković: Lund University
Göran Carlström: Lund University
Michaela Melcher: Lund University
Paolo Bollella: Lund University
Jesper Bendix: University of Copenhagen
Lo Gorton: Lund University
Petter Persson: Lund University
Jens Uhlig: Lund University
Daniel Strand: Lund University

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-28384-8

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