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Phototransformation of 5-nitro-2-furaldehyde in aqueous solution. A laser flash photolysis and product analysis study

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Abstract

Laser flash photolysis of 5-nitro-2-furaldehyde (NFA) in solution shows a short-lived transient absorption with λmax = 475 ± 5 nm, which is relatively insensitive to solvent polarity and is assigned to the lowest triplet state of NFA (3NFA*). In water, the 3NFA* absorption decays to a long-lived absorption, the study of which, at different times after the end of the laser pulse, reveals it to be due to a furyloxyl radical λ max ≈ 375 nm) and to the radical anion NFA’− λmax ≈ 400 nm). These radicals were produced independently to confirm the assignment. The lifetime of 3NFA* depends both on the solvent and the ground-state concentration of NFA. An (n, π*) nature is attributed to 3NFA* on the basis of the propensity of 3NFA* to abstract a hydrogen-atom from the solvent. Kinetic evidence for triplet excimer formation was obtained from the self-quenching of 3NFA* in solvents where the triplet decay is slower. The effect of acidity on the triplet lifetime is discussed with respect to an electron-transfer self-quenching mechanism, assisted by the triplet excimer which is proposed to dissociate into radical ions. Chromatographic and spectroscopic analysis of the photolysed aqueous solution of NFA. enabled the identification of 5-hydroxymethyl-ene-2(5H)-furanone, nitrite ion and an unknown substance as the major photoproducts. Conclusive evidence is presented that the observed 5-hydroxymethylene-2(5H)-furanone is formed from the furyloxyl radical. It is shown that the unknown substance can also be obtained from both the photoreduction of NFA. in propan-2-ol and chemical reduction of NFA. by Fe(s) in water (along with 5-amino-2-furaldehyde) Based on 1H- and 13C-NMR (with 2-D. HMQC) and vibrational absorption spectroscopy, a tentative structure is proposed for the substance of tR 3.69 minutes obtained as a photoreduction product of NFA. in water. Inorganic anions are shown to be one-electron oxidised by 3NFA* (as indicated by the observation of both the radical anion of NFA. and the inorganic radical) with second-order rate constants being dependent on E17 of the inorganic radical. The implications of the results from complete quenching of 3NFA* by inorganic anions, and subsequent product analysis, for the phototransformation mechanism of NFA. in water are discussed.

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    Luis J. A. Martins & João M. M. Ferreira

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Martins, L.J.A., Ferreira, J.M.M. Phototransformation of 5-nitro-2-furaldehyde in aqueous solution. A laser flash photolysis and product analysis study. Photochem Photobiol Sci 16, 721–735 (2017). https://doi.org/10.1039/c6pp00423g

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