Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐p-carboquinoid System
Abstract
An extended π-system containing two [3]cumulene fragments separated by a p-carboquinoid and stabilized by two capping N-heterocyclic carbenes (NHCs) has been prepared. Mono- and bis(imidazolidinium ethynyl) cations have also been synthesized from the reaction of an NHC with phenylethynyl bromide or 1,4-bis(bromoethynyl)benzene. Cyclic voltammetry coupled with synthetic and structural studies showed that the dication is readily reduced to a neutral, singlet bis-1,4-([3]cumulene)-p-carboquinoid as a result of the π-accepting properties of the capping NHCs.
Main Authors
Format
Articles
Research article
Published
2018
Series
Subjects
Publication in research information system
Publisher
Wiley
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-202204272414Käytä tätä linkitykseen.
Review status
Peer reviewed
ISSN
1433-7851
DOI
https://doi.org/10.1002/anie.201711031
Language
English
Published in
Angewandte Chemie
Citation
- Barry, B. M., Soper, R. G., Hurmalainen, J., Mansikkamäki, A., Robertson, K. N., McClennan, W., Veinot, A. J., Roemmele, T. L., Werner‐Zwanziger, U., Boeré, R. T., Tuononen, H. M., Clyburne, J. A. C., & Masuda, J. D. (2018). Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐p-carboquinoid System. Angewandte Chemie, 57(3), 749-754. https://doi.org/10.1002/anie.201711031
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Funder(s)
Emil Aaltonen Foundation
Additional information about funding
J.D.M., J.A.C.C., and R.T.B. acknowledge the support of individual Discovery Grants from the Natural Sciences and Engineering Research Council as well as individual funding from the Canadian Foundation for Innovation, the Nova Scotia Research and Innovation Trust (J.D.M., J.A.C.C.), and the Government of Alberta (R.T.B.). J.A.C.C. is thankful to the Government of Canada for a Canada Research Chair. H.M.T., A.M., and J.H. acknowledge financial support from the University of Jyväskylä and the Emil Aaltonen Foundation as well as computational resources provided by CSC—IT Centre for Science and the Finnish Grid and Cloud Infrastructure (persistent identifier urn:nbn:fi:research infras2016072533). U.W.-Z. acknowledges support from the NMR-3 facility at Dalhousie University. Michel B. Johnson is acknowledged for collecting the magnetic susceptibility data.
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