View More View Less
  • 1 Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 66-342, 02139, Cambridge, MA, USA
  • 2 Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, 02215, Boston, MA, USA
Restricted access

Abstract

In an effort to utilize microfluidics to enable photochemistry, we have devised a method for fabrication of devices with UV-transmissive glass. The photochemical device is successfully incorporated into a system utilizing high-pressure capillary mercury lamps and cooling system. We have demonstrated the ability to carry out photochemical transformations with substantial rate acceleration. Furthermore, we highlight the ability to carry out analytical-scale reactions on a pulse flow automated system while modulating wavelength and residence time to identify optimal photochemical reaction conditions. The analytical conditions were also successfully converted to continuous-flow preparative scale.

  • 1. Coxon, J. M.; Halton, B. Organic Photochemistry; Cambridge University Press: Cambridge, 1987.

  • 2. (a) Hoffmann, N. Chem. Rev. 2008, 108, 10521103.

    (b)Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 20032020.

  • 3. M. Fagnoni D. Dondi D. Ravelli A. Albini 2007 Chem. Rev 107 27252756.

  • 4. P. Esser B. Pohlmann H.-D. Scharf 1994 Angew. Chem. Int. Ed 33 2009.

  • 5. Horspool, W. H. Synthetic Organic Photochemistry; Springer: New York, 1984.

  • 6. H. Lu M. A. Schmidt K. F. Jensen 2001 Lab Chip 1 2228.

  • 7. (a) Webb, D.; Jamison, T. F. Chem. Sci. 2010, 1, 675680.

    (b)Wirth, T. Microreactors in Organic Synthesis and Catalysis; Wiley-VCH: Weinheim, 2008.

    (c)Hartman, R. L.; Jensen, K. F. Lab Chip 2009, 9, 2495.

    (d)Mason, B. P.; Price, K. E.; Steinbacher, J. L.; Bogdan, A. R.; McQuade, D. T. Chem. Rev. 2007, 107, 23002318.

    (e)Geyer, K.; Gustavson, T.; Seeberger, P. H. Synlett 2009, 15, 2382.

    (f)Kirschning, A.; Solodenko, W.; Mennecke, K. Chem. Eur. J. 2006, 12, 5972.

    (g)Watts, P.; Wiles, C. Chem. Commun. 2007, 443467.

    (h)Baxendale, I. R.; Ley, S. V.; Mansfield, A. C.; Smith, C. D. Angew. Chem. Int. Ed. 2009, 48, 40174021.

    (i)Kockmann, N.; Gottsponer, M.; Zimmermann, B.; Roberge, D. M. Chem. Eur. J. 2008, 14, 74707477. ( j) Yoshida, J.-I.; Nagaki, A.; Yamada, T. Chem. Eur. J. 2008, 14, 74507459.

    • Search Google Scholar
    • Export Citation
  • 8. J. R. Goodell ; J. P. McMullen N. Zaborenko J. R. Maloney C. X. Ho K. F. Jensen J. A. Porco A. B. Beeler 2009 J. Org. Chem 74 61696180.

  • 9. (a) Hook, B. D. A.; Dohle, W.; Hirst, P. R.; Pickworth, M.; Berry, M. B.; Booker-Milburn, K. I. J. Org. Chem. 2005, 70, 75587564.

    (b)Sakeda, K.; Wakabayashi, K.; Matsushita, Y.; Ichimura, T.; Suzuki, T.; Wada, T.; Inoue, Y. J. Photochem. Photobiol. Chem. 2007, 192, 166171.

    • Search Google Scholar
    • Export Citation

    (c)Coyle, E. E.; Oelgemoller, M. Photochem. Photobiol. Sci. 2008, 7, 13131322.

    (d)Vasudevan, A.; Villamil, C.; Trumbull, J.; Olson, J.; Sutherland, D.; Pan, J.; Djuric, S. Tetrahedron Lett. 2010, 51, 40074009.

  • 10. Matsushita, Y.; Kumada, S.; Wakabayashi, K.; Sakeda, K.; Ichimura, T. Chem. Lett. 2006, 35, 410411. Schott, Glass 8337B Technical Data. www.us.schott.com/tubing/media/selector/datasheets/english/Glass_8337b_datasheet_english.pdf.

    • Search Google Scholar
    • Export Citation
  • 11. Madou, M. J. Fundamentals of Microfabrication: The Science of Miniaturization; Boca Raton, FL: CRC Press, 2002.

  • 12. J. W. Hanifin E. Cohen 1969 J. Am. Chem. Soc 91 44944499.

  • 13. (a) Zimmerman, H. E.; Wilson, J. W. J. Am. Chem. Soc. 1964, 86, 4036.

    (b)Zimmerman, H. E.; Hancock, K. G. J. Am. Chem. Soc. 1968, 90, 3749.

    (c)Schuster, D. I.; Brown, R. H.; Resnick, B. M. J. Am. Chem. Soc. 1978, 100, 45044512.

    (d)Schuster, D. I.; Rao, J. M. J. Org. Chem. 1981, 46, 15151521.

  • 14. S. C. Shim D. S. Kim D. J. Yoo T. Wada Y. Inoue 2002 J. Org. Chem 67 57185726.

  • 15. D. R. Coulson N. C. Yang 1966 J. Am. Chem. Soc 88 45114512.

  • 16. (a) Fisch, M. H.; Richards, J. H. J. Am. Chem. Soc. 1968, 90, 15471553.

    (b)Natarajan, A.; Tsai, C. K.; Khan, S. I.; McCarren, P.; Houk, K. N.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2007, 129, 98469847.