engleski

Light induced decomposition of ferrocenoyl- nucleobases

When dissolved in organic solvents, e.g. DMSO, and exposed to light, ferrocenoyl-substituted nucleobases start to decompose and the release of free nucleobase occurs, whereas the ferrocene moiety degrades. The photochemical reaction of N9-ferrocenoyl-(6-benzyloxy)purine and N1-ferrocenoyl-5-fluorouracyl in DMSO was studied by NMR spectroscopy in different reaction conditions. DMSO-assisted displacement of cyclopentadiene ring from ferrocene moiety occurs and ring-delegated iron complexes form. The reaction rate and order depend on reaction conditions (dissolved gasses, water from solvent) and molar absorption (extinction) coefficients of ferrocene conjugates. Pseudo-first order kinetics occurs when the red lamp (λ = 645 nm) is used to trigger the reaction, whereas the pseudo-zero order kinetics is observed when the blue lamp (λ = 405 nm) is used. When the nucleobase moiety is replaced by the N, N-diphenyl-carboxamide, the light-sensitivity is also observed. In the contrary when the ferrocene moiety is replaced by a benzene ring, as in N7-4-fluorobenzoyl-purine, the compound is not light-sensitive.

ferrocene, nucleobase, photochemical reaction

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