Conservation of ultrafast photoprotective mechanisms with increasing molecular complexity in sinapoyl malate derivatives

Lewis A Baker (1, 2) , Michael Staniforth (1) , Amandine Flourat (3, 4) , Florent Allais (3, 4) , Vasilios G Stavros (1)

1 Department of Chemistry [University of Warwick]
2 UNIS - University of Surrey
3 ABI - Agro-Biotechnologies Industrielles
4 CEBB - Centre Européen de Biotechnologies et Bioéconomie

Sinapoyl malate is a natural plant sunscreen molecule which protects leaves from harmful ultraviolet radiation. Here, the ultrafast dynamics of three sinapoyl malate derivatives, sinapoyl L-dimethyl malate, sinapoyl L-diethyl malate and sinapoyl L-dit-butyl malate, have been studied using transient electronic absorption spectroscopy, in a dioxane and methanol solvent environment to investigate how well preserved these dynamics remain with increasing molecular complexity. In all cases it was found that, upon photoexcitation, deactivation occurs via a trans-cis isomerisation pathway within~20-30 ps. This cis-photoproduct, formed during photodeactivation, is stable and longed-lived for all molecules in both solvents. The incredible levels of conservation of the isomerisation pathway with increased molecular complexity demonstrate the efficacy of these molecules as ultraviolet photoprotectors, even in strongly perturbing solvents. As such, we suggest these molecules might be well-suited for augmentations to further improve their photoprotective efficacy or chemical compatibility with other components of sunscreen mixtures, whilst conserving their underlying photodynamic properties.

Domaines: Chimie théorique et/ou physique

Lewis A Baker, Michael Staniforth, Amandine Flourat, Florent Allais, Vasilios G Stavros. Conservation of ultrafast photoprotective mechanisms with increasing molecular complexity in sinapoyl malate derivatives. ChemPhysChem, 2020, 21 (17), pp.2006-2011. ⟨10.1002/cphc.202000429⟩. ⟨hal-03473143⟩