Spiropyrans are photochromic compounds that can isomerize in response to UV/vis irradiation as a result of a reversible heterolytic cleavage of the spiro C-O bond followed by cis�trans isomerisation which generates a metastable merocyanine.1 The presence of a negatively charged phenolic oxygen in the zwitterionic open form produces a moiety that can act as a chelating site for a variety of metal ions. By functionalising a photochromic compound with a suitable metal-binding site, it is therefore possible to affect light-induced release of the metal ion and thus a regenerable sensing system.We have developed a novel reversible spiropyran-based photoregenerable receptor that is selective towards zinc(II) ions over a series of biologically and environmentally relevant cations. 1H-NMR studies confirm that the closed form is converted to the open trans-merocyanine complex upon addition of zinc ions.                                                                                   1.   (a) F. M Raymo and S. Giordani, J. Am. Chem. Soc., 2001, 123, 4651. (b) S. Giordani and F.M. Raymo Org. Lett., 2003, 5, 3559-3562.

Spiropyran as a reversible Zn selective receptor

239th National Meeting (2010)

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