Details

Autor(en) / Beteiligte

• 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.
• Tuononen, Heikki M.
• Clyburne, Jason A. C.
• Masuda, Jason D.

Titel

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

Ist Teil von

• Angewandte Chemie International Edition, 2018-01, Vol.57 (3), p.749-754

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2018

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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. Accumulating cumulenes: Two‐electron reduction of a bis(imidazolidinium ethynyl) dication derived from an N‐heterocyclic carbene (NHC) and 1,4‐bis(bromoethynyl)benzene gave the extended bis‐1,4‐([3]cumulene)‐p‐carboquinoid 1 with no change in the overall distance between the NHC moieties. Cyclic voltammetry coupled with synthetic and structural studies showed that the π‐accepting properties of the capping NHCs may play a role in the reduction of the dication.