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Photochemistry without Light: Oxidation of Rubrene in a Microemulsion with a Chemical Source of Singlet Molecular Oxygen (1O2, 1Dg)

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Véronique Nardello , Marie-Josée Marti , Christel Pierlot and Jean-Marie Aubry

ENSCL, Equipe de Recherches "Oxydation et Formulation", BP 108, F-59 652 Villeneuve d''Ascq cedex, France

J. Chem. Educ., 1999, 76 (9), p 1285

DOI: 10.1021/ed076p1285

Publication Date (Web): September 1, 1999

Section:

History, Education, and Documentation

Abstract

This simple experiment illustrates the main features of excited oxygen in the singlet state ¹O₂ (¹D_g): (i) its high oxidizing power and its selectivity towards unsaturated organic compounds, (ii) its low excitation energy which allows its access by various chemical processes and (iii) its long lifetime compared to the other usual excited molecules. In the laboratory experiment presented here, 1O2 is generated through the disproportionation of hydrogen peroxide catalyzed by molybdate ions and is used to carry out the oxidation of a polycyclic aromatic compound, rubrene. As the formation of 1O2 proceeds efficiently only in water, a microemulsion is used as solvent to oxidize this highly hydrophobic substrate. Actually, the microemulsion, which consists of aqueous microdroplets surrounded by a continuous organic phase, allows considerable amounts of hydrophilic reactants (H₂O₂ and MoO₄^2-) and hydrophobic organic substrates to dissolve simultaneously. The typical size of the microdroplets (Âª 10-50 nm) is much smaller than the mean travel distance of ¹O₂ in water (Âª 200 nm). Therefore, ¹O₂ can diffuse, before deactivation by water, into the organic phase where the oxidation of the substrate can take place.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Colloids

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

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Diffusion of Aromatic Hydrocarbons in n-Alkanes and Cyclohexanes
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  The translational diffusion constants, D, of biphenyl, diphenylacetylene, diphenylbutadiyne, anthracene, pyrene, rubrene, perylene, and coronene have been determined in the n-alkanes using capillary flow techniques. Pyrene and rubrene were also studied in ...
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