A1 Journal article (refereed)
Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐p-carboquinoid System (2018)

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

JYU authors or editors

Publication details

All authors or editors: Barry, Brian M.; Soper, R. Graeme; Hurmalainen, Juha; Mansikkamäki, Akseli; Robertson, Katherine N.; McClennan, William, L.; Veinot, Alex J.; Roemmele, Tracey L.; Werner‐Zwanziger, Ulrike; Boeré, René T.; et al.

Journal or series: Angewandte Chemie

ISSN: 1433-7851

eISSN: 1521-3773

Publication year: 2018

Publication date: 15/01/2018

Volume: 57

Issue number: 3

Pages range: 749-754

Publisher: Wiley

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.1002/anie.201711031

Publication open access: Not open

Publication channel open access: 

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/80741

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.

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Ministry reporting: Yes

Preliminary JUFO rating: 3