Issue 3, 2012
From the journal:

Photochemical & Photobiological Sciences

Aromatic aldols and 1,5-diketones as optimized fragrance photocages†

Axel G. Griesbeck,*a   Olga Hinze,a   Helmut Görner,b   Ursula Huchel,c   Christian Kropf,c   Uta Sundermeierc  and  Thomas Gerkec  

* Corresponding authors

a Department of Chemistry, University of Cologne, Greinstr, 4, 50939 Köln, Germany

b Max-Planck-Institut für Bioanorganische Chemie, 45413 Mülheim an der Ruhr, Germany

c Henkel AG & Co. KGaA, Henkelstr, 67, 40589 Düsseldorf, Germany
E-mail: griesbeck@uni-koeln.de

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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Article information

DOI
https://doi.org/10.1039/C2PP05286E
Article type
Paper
Submitted
07 Sep 2011
Accepted
12 Jan 2012
First published
10 Feb 2012

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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