Direct Photooxidation and Xanthene-Sensitized Oxidation of Naphthols: Quantum Yields and Mechanism

Oelgemoeller M, Mattay J, Goerner H (2011)
The Journal of Physical Chemistry A 115(3): 280-285.

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The photoinduced oxidation of 1-naphthol to 1,4-naphthoquinone and of 5-hydroxy-1-naphthol to 5-hydroxy-1,4-naphthoquinone was studied by steady-state and time-resolved techniques. The direct photooxidation of naphthols in methanol or water takes place by reaction of the naphoxyl radical ((center dot)ONaph) with the superoxide ion radical (O-2(center dot-)), the latter of which results from the reaction of the solvated electron with oxygen after photoionization. The sensitized oxidation takes place by energy transfer from the xanthene triplet state to oxygen. From the two oxygen atoms, which are consumed, one is incorporated into the naphthol molecule giving naphthoquinone and the second gives rise to water. The effects of eosin, erythrosin, and rose bengal in aqueous solution, pH, and the oxygen and naphthol concentrations were studied. The quantum yield of the photosensitized transformation was determined, which increases with the naphthol concentration and is largest at pH > 10. The quantum yield of oxygen uptake is similar. The pathway involving singlet molecular oxygen is suggested to operate for the three sensitizers. The alternative pathway via electron transfer from the naphthol to the xanthene triplet state and subsequent reaction of (center dot)ONaph with O2(center dot-), the latter of which is formed by scavenging of the xanthene radical anion by oxygen, does also contribute.
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Oelgemoeller M, Mattay J, Goerner H. Direct Photooxidation and Xanthene-Sensitized Oxidation of Naphthols: Quantum Yields and Mechanism. The Journal of Physical Chemistry A. 2011;115(3):280-285.
Oelgemoeller, M., Mattay, J., & Goerner, H. (2011). Direct Photooxidation and Xanthene-Sensitized Oxidation of Naphthols: Quantum Yields and Mechanism. The Journal of Physical Chemistry A, 115(3), 280-285.
Oelgemoeller, M., Mattay, J., and Goerner, H. (2011). Direct Photooxidation and Xanthene-Sensitized Oxidation of Naphthols: Quantum Yields and Mechanism. The Journal of Physical Chemistry A 115, 280-285.
Oelgemoeller, M., Mattay, J., & Goerner, H., 2011. Direct Photooxidation and Xanthene-Sensitized Oxidation of Naphthols: Quantum Yields and Mechanism. The Journal of Physical Chemistry A, 115(3), p 280-285.
M. Oelgemoeller, J. Mattay, and H. Goerner, “Direct Photooxidation and Xanthene-Sensitized Oxidation of Naphthols: Quantum Yields and Mechanism”, The Journal of Physical Chemistry A, vol. 115, 2011, pp. 280-285.
Oelgemoeller, M., Mattay, J., Goerner, H.: Direct Photooxidation and Xanthene-Sensitized Oxidation of Naphthols: Quantum Yields and Mechanism. The Journal of Physical Chemistry A. 115, 280-285 (2011).
Oelgemoeller, Michael, Mattay, Jochen, and Goerner, Helmut. “Direct Photooxidation and Xanthene-Sensitized Oxidation of Naphthols: Quantum Yields and Mechanism”. The Journal of Physical Chemistry A 115.3 (2011): 280-285.
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