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Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐ p ‐carboquinoid System
Author(s) -
Barry Brian M.,
Soper R. Graeme,
Hurmalainen Juha,
Mansikkamäki Akseli,
Robertson Katherine N.,
McClennan William L.,
Veinot Alex J.,
Roemmele Tracey L.,
WernerZwanziger Ulrike,
Boeré René T.,
Tuon Heikki M.,
Clyburne Jason A. C.,
Masuda Jason D.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711031
Subject(s) - cumulene , dication , chemistry , bromide , cyclic voltammetry , singlet state , benzene , medicinal chemistry , photochemistry , molecule , organic chemistry , electrochemistry , excited state , physics , electrode , nuclear physics
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.