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Supramolecular control of [2 + 2] photodimerization via hydrogen bonding
Vincent Darcos1, Kirsten Griffith, Xavier Sallenave
1Groupe de Chimie Supramoléculaire, Biomimétisme et Nanosciences, Université Bordeaux I, LCOO CNRS UMR 5802, 33405 Talence, France.
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.