Abstract
The synthesis of biomimetic photosynthetic model compounds, composed of 5,10,15-triphenylporphyrins covalently linked to redox active crown ether quinones via different bridges, is described. Using the zinc complex with the flexible butylene spacer in non polar solvents backfolding of the crown ether quinone over the porphyrin plane is observed by 1H NMR chemical shift studies. This conformational effect is supported by molecular modelling calculations. The backfolding is induced by complexation of the acceptor with the central atom since it is not observed in the metal free-base porphyrin derivative. Due to steric constraints the zinc porphyrin cyclohexylene crown ether quinones lack this backfolding. Cyclic voltammetry measurements show a significant shift of the reduction potential of the quinone crown ether moiety in the presence of alkali metal cations.
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