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Issue 3, 2012
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Aromatic aldols and 1,5-diketones as optimized fragrance photocages

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Abstract

Aromatic aldols and 1,5-diketones with abstractable γ-hydrogen atoms are highly photoactive cage molecules for the release of fragrance carbonyl compounds (aldehydes and Michael ketones, respectively). Aldols 3a–d are easily accessible by Mukaiyama addition and are cleaved to form the substrates with high quantum yields under solar radiation. By tuning the properties of the chromophores, a series of δ-damascone cages 5 were developed that can be used for selective and fast (5a,e) or slow (5b,d) release of fragrances under air and solar irradiation. The intermediates of the Norrish II process were observed by laser transient absorption spectroscopy.

Graphical abstract: Aromatic aldols and 1,5-diketones as optimized fragrance photocages

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Publication details

The article was received on 07 Sep 2011, accepted on 12 Jan 2012 and first published on 10 Feb 2012


Article type: Paper
DOI: 10.1039/C2PP05286E
Citation: Photochem. Photobiol. Sci., 2012,11, 587-592
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    Aromatic aldols and 1,5-diketones as optimized fragrance photocages

    A. G. Griesbeck, O. Hinze, H. Görner, U. Huchel, C. Kropf, U. Sundermeier and T. Gerke, Photochem. Photobiol. Sci., 2012, 11, 587
    DOI: 10.1039/C2PP05286E

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