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Title: Perinaphthenone phototransformation in a model of leaf epicuticular waxes
Authors: Trivella, Aurelien S.
Monadjemi, Shirin
Worrall, David R.
Kirkpatrick, Iain
Arzoumanian, Emmanuel
Richard, Claire
Keywords: Perinaphthenone
Singlet oxygen
Epicuticular wax
Hydroxyperinaphthenyl radical
Pyrethrum extract
Issue Date: 2014
Publisher: © Elsevier
Citation: TRIVELLA, A.S. ... et al, 2014. Perinaphthenone phototransformation in a model of leaf epicuticular waxes. Journal of Photochemistry and Photobiology B- Biology, 130, pp. 93 - 101.
Abstract: Perinaphthenone (1H-phenalen-1-one, PN) is a reference photosensitizer producing singlet oxygen with a quantum yield close to one in a large variety of solvents. It is also the basic structure of a class of phototoxic phytoalexins. In this work, the PN photoreactivity was studied for the first time in a paraffinic wax, used as model of leaf epicuticular waxes. The PN photodegradation was monitored by UV–Vis spectroscopy. The triplet excited state, singlet oxygen and the hydroxyperinaphthenyl radical were detected by diffuse reflectance laser flash photolysis, near infrared phosphorescence and by EPR spectroscopy, respectively. The PN phototransformation was found to be fivefold faster in the wax than in n-heptane under steady-state irradiation. The hydroxyperinaphthenyl radical formation was observed in aerated irradiated paraffin wax while in n-heptane solution the radical was observed only in the absence of oxygen. These results show that under continuous irradiation, PN is much more easily phototransformed in a solid environment than in solution. Several photoproducts were identified, in particular phenalanone, PN dimers, and oxidized PN-alkanes adducts. Finally, when pyrethrum extract is added into the wax along with PN, the hydroxyperinaphthenyl radical concentration was increased by a factor of 2.4. Such photochemical reactions may occur when systemic pesticides enter the plant cuticle.
Description: This article was accepted for publication in the serial, Journal of Photochemistry and Photobiology B- Biology [© Elsevier]. The definitive version is available at: http://dx.doi.org/10.1016/j.jphotobiol.2013.10.009
Version: Accepted for publication
DOI: 10.1016/j.jphotobiol.2013.10.009
URI: https://dspace.lboro.ac.uk/2134/18469
Publisher Link: http://dx.doi.org/10.1016/j.jphotobiol.2013.10.009
ISSN: 1011-1344
Appears in Collections:Published Articles (Chemistry)

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