Wavepacket insights into the photoprotection mechanism of the UV filter methyl anthranilate

Rodrigues, Natércia d.  N.; Cole-Filipiak, Neil C.; Blodgett, Karl N.; Abeysekera, Chamara; Zwier, Timothy S.; Stavros, Vasilios G.

doi:10.1038/s41467-018-07681-1

Title: Wavepacket insights into the photoprotection mechanism of the UV filter methyl anthranilate

Journal Article · 04 December 2018 · Nature Communications

DOI: https://doi.org/10.1038/s41467-018-07681-1 · OSTI ID:1624130

Rodrigues, Natércia d. N. ^[1];

^[2];

^[3]; Abeysekera, Chamara ^[3]; Zwier, Timothy S. ^[3]; Stavros, Vasilios G. ^[4]

University of Warwick, Coventry (United Kingdom), Department of Chemistry; DOE/OSTI
Sandia National Lab. (SNL-CA), Livermore, CA (United States), Combustion Research Facility; University of Warwick, Coventry (United Kingdom), Department of Chemistry
Purdue Univ., West Lafayette, IN (United States), Dept. of Chemistry
University of Warwick, Coventry (United Kingdom), Department of Chemistry

Meradimate is a broad-spectrum ultraviolet absorber used as a chemical filter in commercial sunscreens. Herein, we explore the ultrafast photodynamics occurring in methyl anthranilate (precursor to Meradimate) immediately after photoexcitation with ultraviolet radiation to understand the mechanisms underpinning Meradimate photoprotection. Using time-resolved photoelectron spectroscopy, signal from the first singlet excited state of methyl anthranilate shows an oscillatory behavior, i.e., quantum beats. Our studies reveal a dependence of the observed beating frequencies on photoexcitation wavelength and photoelectron kinetic energy, unveiling the different Franck-Condon overlaps between the vibrational levels of the ground electronic, first electronic excited, and ground cationic states of methyl anthranilate. By evaluating the behavior of these beats with increasing photon energy, we find evidence for intramolecular vibrational energy redistribution on the first electronic excited state. Such energy redistribution hinders efficient relaxation of the electronic excited state, making methyl anthranilate a poor choice for an efficient, efficacious sunscreen chemical filter.

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Research Organization:: Purdue Univ., West Lafayette, IN (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: FG02-96ER14656

OSTI ID:: 1624130

Journal Information:: Nature Communications, Journal Name: Nature Communications Journal Issue: 1 Vol. 9; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

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Wavepacket insights into the photoprotection mechanism of the UV filter methyl anthranilate d. N. Rodrigues, Natércia; Cole-Filipiak, Neil C.; Blodgett, Karl N. Zenodo https://doi.org/10.5281/zenodo.1472500	dataset	January 2018
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Photophysics of the sunscreen ingredient menthyl anthranilate and its precursor methyl anthranilate: A bottom-up approach to photoprotection Rodrigues, N. D. N.; Cole-Filipiak, N. C.; Horbury, M. D. Journal of Photochemistry and Photobiology A: Chemistry, Vol. 353 https://doi.org/10.1016/j.jphotochem.2017.11.042	journal	February 2018
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A Perspective on the Ultrafast Photochemistry of Solution-Phase Sunscreen Molecules Baker, Lewis A.; Greenough, Simon E.; Stavros, Vasilios G. The Journal of Physical Chemistry Letters, Vol. 7, Issue 22 https://doi.org/10.1021/acs.jpclett.6b02104	journal	November 2016
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UV-induced DNA damage and repair: a review Sinha, Rajeshwar P.; Häder, Donat-P. Photochemical & Photobiological Sciences, Vol. 1, Issue 4 https://doi.org/10.1039/b201230h	journal	March 2002
Deducing anharmonic coupling matrix elements from picosecond time-resolved photoelectron spectra: application to S1 toluene at low vibrational energy Davies, Julia A.; Green, Alistair M.; Reid, Katharine L. Physical Chemistry Chemical Physics, Vol. 12, Issue 33 https://doi.org/10.1039/c0cp00102c	journal	January 2010
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Time-resolved velocity map ion imaging study of NH3 photodissociation Wells, Kym L.; Perriam, Gareth; Stavros, Vasilios G. The Journal of Chemical Physics, Vol. 130, Issue 7 https://doi.org/10.1063/1.3072763	journal	February 2009
Toward real-time charged-particle image reconstruction using polar onion-peeling Roberts, G. M.; Nixon, J. L.; Lecointre, J. Review of Scientific Instruments, Vol. 80, Issue 5 https://doi.org/10.1063/1.3126527	journal	May 2009
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Evolution under the sun: optimizing light harvesting in photosynthesis Ruban, A. V. Journal of Experimental Botany, Vol. 66, Issue 1 https://doi.org/10.1093/jxb/eru400	journal	October 2014
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Torsional Motion of the Chromophore Catechol following the Absorption of Ultraviolet Light Young, J. D.; Staniforth, M.; Paterson, M. J. Physical Review Letters, Vol. 114, Issue 23 https://doi.org/10.1103/PhysRevLett.114.233001	journal	June 2015
The Protective Role of Melanin Against UV Damage in Human Skin† Brenner, Michaela; Hearing, Vincent J. Photochemistry and Photobiology, Vol. 84, Issue 3 https://doi.org/10.1111/j.1751-1097.2007.00226.x	journal	November 2007
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UV Radiation and the Skin D'Orazio, John; Jarrett, Stuart; Amaro-Ortiz, Alexandra International Journal of Molecular Sciences, Vol. 14, Issue 6 https://doi.org/10.3390/ijms140612222	journal	June 2013
Wavepacket insights into the photoprotection mechanism of the UV filter methyl anthranilate d. N. Rodrigues, Natércia; Cole-Filipiak, Neil C.; Blodgett, Karl N. Zenodo https://doi.org/10.5281/zenodo.1472500	dataset	January 2018

Cited By (4)

Ultrafast photodissociation dynamics of 2-ethylpyrrole: adding insight to experiment with ab initio multiple cloning Green, James A.; Makhov, Dmitry V.; Cole-Filipiak, Neil C. Physical Chemistry Chemical Physics, Vol. 21, Issue 7 https://doi.org/10.1039/c8cp06359a	journal	January 2019
Ultrafast photodissociation dynamics of pyrazole, imidazole and their deuterated derivatives using ab initio multiple cloning Symonds, Christopher C.; Makhov, Dmitry V.; Cole-Filipiak, Neil C. Physical Chemistry Chemical Physics, Vol. 21, Issue 19 https://doi.org/10.1039/c9cp00039a	journal	January 2019
Vibronic spectroscopy of methyl anthranilate and its water complex: hydrogen atom dislocation in the excited state Blodgett, Karl N.; Sun, Dewei; Fischer, Joshua L. Physical Chemistry Chemical Physics, Vol. 21, Issue 38 https://doi.org/10.1039/c9cp04556b	journal	January 2019
Applications of ultrafast spectroscopy to sunscreen development, from first principles to complex mixtures Holt, Emily L.; Stavros, Vasilios G. International Reviews in Physical Chemistry, Vol. 38, Issue 2 https://doi.org/10.1080/0144235x.2019.1663062	journal	April 2019

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