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Supramolecular control of [2 + 2] photodimerization via hydrogen bonding

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Abstract

The use of supramolecular catalysis to control the photoinduced dimerization of styrene, cinnamate, and stilbene chromophores is reported. The strategy employs the formation of a 2 : 1 supramolecular assembly in the presence of 5,5-dihexylbarbituric acid (DHB). A 3- to 10-fold increase in dimerization efficiency is observed in its presence, concomitant with accrued selectivity for the syn photodimers. The origin of the regioselectivity in the presence of DHB is discussed in terms of topochemical control within the supramolecular architecture.

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Authors and Affiliations

  1. Groupe de Chimie Supramoléculaire, Biomimétisme et Nanosciences, Université Bordeaux I, LCOO CNRS UMR 5802, 33405, Talence, France

    Vincent Darcos, Kirsten Griffith, Xavier Sallenave, Jean-Pierre Desvergne & Dario M. Bassani

  2. Laboratoire de Chimie Inorganique et Matériaux Moléculaires, Université Pierre et Marie Curie, CNRS UMR 7071, 75252, Paris, France

    Carine Guyard-Duhayon & Bernold Hasenknopf

Authors
  1. Vincent Darcos
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  2. Kirsten Griffith
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  3. Xavier Sallenave
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  4. Jean-Pierre Desvergne
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  5. Carine Guyard-Duhayon
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  6. Bernold Hasenknopf
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  7. Dario M. Bassani
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Correspondence to Dario M. Bassani.

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This paper is dedicated to Professor Fred Lewis on the event of his 60th birthday.

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Darcos, V., Griffith, K., Sallenave, X. et al. Supramolecular control of [2 + 2] photodimerization via hydrogen bonding. Photochem Photobiol Sci 2, 1152–1161 (2003). https://doi.org/10.1039/b307525g

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