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Redox Switching in Ethenyl- Bridged Bisphospholes
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
2014 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 49, 16083-16087 p.Article in journal (Refereed) Published
Abstract [en]

A 2e(-)/2H(+) redox platform has been implemented in the ethenyl-bridged bisphosphol-3-ol 1 to afford the first phospholes that feature chemically reversible oxidations. Oxidation of the title compounds to the corresponding bisphosphol-3-one 2 leads to a change in conjugation topology and a concomitant hypsochromic shift of the lowest-energy absorption maximum by 100nm. Electrochemical oxidation proceeds without any detectable intermediates, whereas the deprotonated form of 1 can be observed in an aprotic medium during the reduction of 2. This dianionic intermediate 3 is characterized by end absorptions that are bathochromically shifted by circa 200nm compared to those of 2.

Place, publisher, year, edition, pages
2014. Vol. 20, no 49, 16083-16087 p.
Keyword [en]
conjugation, cyclic voltammetry, electrochromism, phosphaorganic chemistry
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-240068DOI: 10.1002/chem.201405525ISI: 000345515700008PubMedID: 25346007OAI: oai:DiVA.org:uu-240068DiVA: diva2:775966
Available from: 2015-01-05 Created: 2015-01-05 Last updated: 2017-12-05Bibliographically approved

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Arkhypchuk, Anna I.Mijangos, EdgarLomoth, ReinerOtt, Sascha

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