Journal of the Brazilian Chemical Society
Print version ISSN 0103-5053
NEUMANN, Miguel G et al. Photooxidative degradation of QTX (a thioxanthone derivative). J. Braz. Chem. Soc. [online]. 2011, vol.22, n.2, pp. 217-222. ISSN 0103-5053. http://dx.doi.org/10.1590/S0103-50532011000200005.
The photooxidative degradation of QTX (2-hydroxy-3-(3,4-dimethyl-9-oxo-9H-thioxanthen-2-yloxy)-N,N,N-trimethyl-1-propanium chloride) has been investigated and photoproducts from QTX degradation in aqueous solution were characterized using HPLC/ESI-MS. The photooxidation of the dye was monitored by electronic absorption spectroscopy. The spectrum of the dye shows bands at 273 and 402 nm. During irradiation, the intensity of these bands decreases together with the appearance of a band at 310-340 nm, typical of oxidized QTX. The chromatograms show the presence of new peaks due to photoproducts of QTX degradation that were identified by mass spectroscopy. The peaks at m/z 388, 420 and 270 were attributed to photoproducts, whereas the peak at m/z 372 is due to QTX. The peak at m/z 388 corresponds to the formation of a sulfoxide group and that at m/z 420 suggested the formation of a sulfone with a hydroxyl on the methyl group. The peak at m/z 270 suggests that oxygen reacts with QTX abstracting a hydrogen atom from the carbon bonded the hydroxyl, together with the release of the amino group.
Keywords : substituted thioxanthones; photodegradation; QTX; photopolymerization; photosensitizers; photoinitiators.