Journal
DALTON TRANSACTIONS
Volume -, Issue 17, Pages 2662-2669Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b406009a
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Ligands bearing two salicylidene imine moieties substituted in ortho and para positions by tert-butyl groups have been electrochemically oxidized into mono- and bis-phenoxyl radicals. The process involves an intramolecular proton coupled to electron transfer and affords a radical in which the oxygen atom is hydrogen-bonded to a protonated ammonium or iminium group. A weak intramolecular dipolar interaction exists between the two phenoxyl moieties in the bis-radical species. The copper(II) complexes of these ligands have been characterized and electrochemically oxidized. The monophenoxyl radical species are X- band EPR silent. The bis-phenoxyl radical species exhibits a (S=3/2) ground state: it arises from a ferromagnetic exchange coupling between the two spins of the radicals and that of the copper( II) when the spacer is rigid enough; a flexible spacer such as ethylidene induces decomplexation of at least one phenoxyl group. Metal coordination is more efficient than hydrogen-bonding to enhance the chemical stability of the mono- phenoxyl radicals.
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