Tetrakis(2-methyl-5-methylthiothien-3-yl)ethene (1) exhibits incomplete photochromism in the powder state, KBr pellet, the amorphous state and a polystyrene film. In contrast, 1 in the single crystalline state does not show any photoreactivity. This chromic system involves three possible photon-modes involving the starting open isomer 1, the corresponding closed isomer trans- 2 and the rearranged isomer trans- 3. Unfortunately, efforts to control the interconversions between these isomers, especially the rearrangement of trans- 2 to trans- 3, have not been fruitful. A possible mechanism for photocyclization of 1 to form trans- 2 is also discussed on the basis of the results of density functional theory calculations together with that for the 1,2-dyotropic rearrangement of trans- 2 to give trans- 3.
Research on Chemical Intermediates – Springer Journals
Published: Oct 14, 2009
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