Redox switching in ethenyl-bridged bisphospholes.


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.

DOI: 10.1002/chem.201405525

Cite this paper

@article{Arkhypchuk2014RedoxSI, title={Redox switching in ethenyl-bridged bisphospholes.}, author={Anna I Arkhypchuk and Edgar Mijangos and Reiner Lomoth and Sascha Ott}, journal={Chemistry}, year={2014}, volume={20 49}, pages={16083-7} }