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36h

Microphotochemistry - Photochemistry in Microstructured Reactors

Michael Oelgemöller1, Sonia Gallagher2, Su Bee Tan2, Fei Chen2, and Mirek Macka2. (1) School of Pharmacy and Molecular Sciences, James Cook University, Townsville, Australia, (2) School of Chemical Sciences, Dublin City University, Dublin, Ireland

There has been increased interest shown in the area of microphotochemistry as it can be utilised for a wide range of synthetic applications.[1,2] Generally speaking, micro-photoreactors have a number of advantages over conventional batch photoreactors, which also makes them more beneficial for ‘green chemistry':

We have demonstrated the potential of microphotochemistry using various model photoreactions, i.e. photoinduced electron transfer reactions involving phthalimides[3] or furanones.[4] All reactions were studied in a commercially available glass reactor (Figure) and were compared to results obtained using conventional Rayonet chamber reactors.

Figure: A glass microreactor (Dwell device, mikroglas) under a UV exposure panel. A five Euro-cent coin is used to illustrate the size of the reactor.

In almost all cases examined the reactions performed in the microreactor gave far higher conversions and consequently yields thus proving the superiority of the microphotochemistry concept.

In an extension of this work, we have demonstrated that photochemical additions to furanones can be achieved in microcapillaries using LEDs.

This research project was funded by Science Foundation Ireland (SFI) and the Environmental Protection Agency (EPA).

[1] Y. Matsushita, T. Ichimura, N. Ohba, S. Kiumada, K. Sakeda, T. Suzuki, H. Tanibata, T. Murata, Pure Appl. Chem., 2007, 79, 1959.

[2] E. Coyle, M. Oelgemöller, Photochem. Photobiol. Sci., 2008, 7, 1313.

[3] (a) M. Oelgemöller, P. Cygon, J. Lex, A. G. Griesbeck, Heterocycles, 2003, 59, 669; (b) A. G. Griesbeck, W. Kramer, M. Oelgemöller, Synlett, 1999, 1169.

[4] (a) S. Bertrand, N. Hoffmann, J.-P. Pete, Eur. J. Org. Chem., 2000, 2227; (b) N. Hoffmann, Tetrahedron: Asymm., 1994, 5, 879.