Redox Switching in Ethenyl‐Bridged Bisphospholes |
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Authors: | Dr Anna I Arkhypchuk Dr Edgar Mijangos Dr Reiner Lomoth Dr Sascha Ott |
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Institution: | Department of Chemistry, ?ngstr?m Laboratories, Uppsala University, Box 523, 75120 Uppsala (Sweden) |
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Abstract: | 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 100 nm. 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 200 nm compared to those of 2 . |
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Keywords: | conjugation cyclic voltammetry electrochromism phosphaorganic chemistry |
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