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Electro-mechanically switchable hydrocarbons based on [8]annulenes

Tasić, Magdalena LU ; Ivković, Jakov LU ; Carlström, Göran LU orcid ; Melcher, Michaela LU ; Bollella, Paolo ; Bendix, Jesper ; Gorton, Lo LU ; Persson, Petter LU ; Uhlig, Jens LU and Strand, Daniel LU (2022) In Nature Communications 13(1).
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... (More)

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.

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author
; ; ; ; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Nature Communications
volume
13
issue
1
article number
860
publisher
Nature Publishing Group
external identifiers
  • scopus:85124679898
  • pmid:35165264
ISSN
2041-1723
DOI
10.1038/s41467-022-28384-8
language
English
LU publication?
yes
additional info
Publisher Copyright: © 2022, The Author(s).
id
39656855-d80a-45a3-9166-9986b97d36d9
date added to LUP
2022-03-28 12:39:37
date last changed
2025-01-01 21:12:57
@article{39656855-d80a-45a3-9166-9986b97d36d9,
  abstract     = {{<p>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.</p>}},
  author       = {{Tasić, Magdalena and Ivković, Jakov and Carlström, Göran and Melcher, Michaela and Bollella, Paolo and Bendix, Jesper and Gorton, Lo and Persson, Petter and Uhlig, Jens and Strand, Daniel}},
  issn         = {{2041-1723}},
  language     = {{eng}},
  number       = {{1}},
  publisher    = {{Nature Publishing Group}},
  series       = {{Nature Communications}},
  title        = {{Electro-mechanically switchable hydrocarbons based on [8]annulenes}},
  url          = {{http://dx.doi.org/10.1038/s41467-022-28384-8}},
  doi          = {{10.1038/s41467-022-28384-8}},
  volume       = {{13}},
  year         = {{2022}},
}