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2-Acetylindan-1,3-dione and its Cu2+ and Zn2+ complexes as promising sunscreen agents

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Synopsis In continuation of a previous spectroscopic and quantum chemical study on 2-acetylindan-1,3-dione (2AID), the spectral properties and photostability of 2AID and its Cu and Zn complexes in different solvents are reported. Comparison is made with the photostability of two commercially available sunscreens: benzophenone-3 and octylmethoxycinnamate. 2AID exhibits a higher photostability, high molar absorption coefficient (42 000 m cm) at and broad-spectrum UV-protection properties. The hypothesis that the strong intramolecular H-bonding is responsible for the higher photostability was confirmed by studying the photodegradation upon irradiation with UV light of 2AID in hydrogen bond-breaking solvent, DMSO. The data obtained show that 2AID undergoes rapid degradation in this solvent.It is found that Cu and Zn−2AID complexes show higher photostability in DMSO than 2AID itself.

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Résumé

A la suite d'une étude préalable en Chimie Spectroscopique et quantique, portant sur le 2-Acetylindan-1,3 dione (2AID), les propriétés spectrales et de photo stabilité du 2AID et ses complexes de Cu2+ et Zn2+ dans différents solvants sont rapportées ici. La comparaison avec la photo stabilité de 2 filtres solaires commerciaux – Benzophenone-3 et l'Octylmethoxycinnamate a été conduite. Le 2AID montre une photo stabilité supérieure, un coefficient d'extinction élevé (42 000 m−1 cm−1) à sa λ max et des propriétés de protection à large spectre.

L'hypothèse que la forte liaison Hydrogène intramoléculaire est responsable de la plus forte photo stabilité a été confirmée par l'étude de sa photo dégradation sous irradiation UV du 2AID dans un milieu solvant dissociant ces liaisons, le DMSO.

Il est montré, de plus, que les complexes de Cu2+ et Zn2+ du 2AID sont plus photo stables dans ce solvant que le 2AID seul.
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Keywords: 2-acetylindan-1; 3-dione; Cu2+ and Zn2+ complexes; intramolecular proton transfer; photostability; sunscreen

Document Type: Research Article

Affiliations: 1: Department of Chemistry, University of Sofia, 1126 Sofia, and 2: Institute of Organic Chemistry, Bulgarian Academy of Sciences, 1113 Sofia, Bulgaria

Publication date: February 1, 2002

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