Mediation of retinal photoisomerization by adduct formation with tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)-europium(II).

Several retinal isomers are shown to form adducts in isooctane solution with a lanthanide beta-diketonate complex, tris(6,6,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium(III) [Eu(fod)3]. The adducts are characterized by an absorption band whose lambda max at approximately 420 nm is red-shifted by approximately 60 nm from the lowest-energy absorption band in the free retinal isomers. Irradiation into this adduct band leads to photoisomerization. For example, photolysis of a 1 mM all-trans-retinal/3 mM Eu(fod)3 isooctane solution at 514.5 nm leads, with reasonable quantum efficiency (phi greater than or equal to 0.05), to isomeric mixtures that are considerably different from these produced with UV excitation in the absence of Eu(fod)3. Particularly noteworthy for a photolysis conducted in a nonpolar solvent is the presence of an appreciable quantity of 11-cis-retinal in the adduct photolysate.