New chemistry of oxophlorins (oxyporphyrins) and their π-radicals
作者： Richard G. Khoury , Laurent Jaquinod , Roberto Paolesse , Kevin M. Smith
DOI: 10.1016/S0040-4020(99)00319-1
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摘要: Abstract Syntheses of novel 15-substituted-oxophlorins via the MacDonald condensation diformyl-dipyrroketones and 5-substituted-dipyrromethanes are described. The electronic steric features 15-substituent enable facile control over oxidation potential oxophlorins. Introduction an electron-withdrawing group efficiently minimizes formation oxophlorin π-radicals. Stabilization neutral π radicals is promoted by hyperconjugation with a 15-tert-butyl group. A sterically induced stabilization non-aromatic tautomer oxophlorin, so-called “iso-oxophlorin” demonstrated. These species exist also as 15-iso-oxophlorins upon complexation to divalent metals. Radical formation, enhanced mild oxidants such K3FeCN6, yielded pure oligomers stereospecific supramolecular arrays radical dimerizations taking place at 10- 10′-positions.
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