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Substituent position effects on sunscreen photodynamics : a closer look at methyl anthranilate

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Rodrigues, Natércia das Neves, Cole-Filipiak, Neil C., Turner, Matthew A. P., Krokidi, Konstantina, Thornton, Georgia L., Richings, Gareth, Hine, Nicholas and Stavros, Vasilios G. (2018) Substituent position effects on sunscreen photodynamics : a closer look at methyl anthranilate. Chemical Physics , 515 . pp. 596-602. doi:10.1016/j.chemphys.2018.08.001 ISSN 0301-0104.

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Official URL: http://dx.doi.org/10.1016/j.chemphys.2018.08.001

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Abstract

Towards the development of a bottom-up rationale for sunscreen design, the effects of substituent position on the ultrafast photodynamics of the sunscreen precursor methyl anthranilate (MA, an ortho compound) were evaluated by studying para- and meta-MA in vacuum. Time-resolved ion yield (TR-IY) measurements reveal a long-lived S1 excited state (≫ 1.2 ns) for para-MA, proposed to be the result of a weakly fluorescent, bound excited state. In the case of meta-MA, TR-IY transients reveal a much faster (∼2 ns) excited state relaxation, possibly due to multiple low-lying S1/S0 conical intersections of prefulvenic character. While meta-MA may not be an ideal sunscreen ingredient due to a low ultraviolet absorbance, its comparatively efficient relaxation mechanism may constitute an alternative to common sunscreen relaxation pathways. Thus, our results should prompt further studies of prefulvenic relaxation pathways in potential sunscreen agents.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
R Medicine > RS Pharmacy and materia medica
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
Faculty of Science, Engineering and Medicine > Science > Physics
Library of Congress Subject Headings (LCSH): Sunscreens (Cosmetics), Photochemistry
Journal or Publication Title: Chemical Physics
Publisher: Elsevier BV
ISSN: 0301-0104
Official Date: 14 November 2018
Dates:
DateEvent
14 November 2018Published
3 August 2018Available
2 August 2018Accepted
Volume: 515
Page Range: pp. 596-602
DOI: 10.1016/j.chemphys.2018.08.001
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Open Access (Creative Commons)
Date of first compliant deposit: 20 August 2018
Date of first compliant Open Access: 3 August 2019
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
EP/L015307/1[EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
EP/P02209X/1[EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
EP/J007153 [EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
EP/N010825[EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266
UNSPECIFIED[RS] Royal Societyhttp://dx.doi.org/10.13039/501100000288
UNSPECIFIEDLeverhulme Trusthttp://dx.doi.org/10.13039/501100000275
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