This research extends I.M. Heilbron et al.'s report of the solid state reversed photochromicity of cinnamaldehyde semicarbazones, investigating the effect on the photochromicity of switching the alkene with an alkyne. Phenylpropynal was prepared in 60% from phenylacetylene and DMF, and used to form the phenylpropynal semicarbazone in 33% after recrystallization. Surprisingly, a mixture of 1:1 syn and anti isomers was formed. The phenylpropynal will also be used to prepare (by a Wittig reaction) an extended conjugation system of an enyne. The syntheses of phenylpropynals with substitutents on the aryl ring were attempted via both a vinyl phosphate route and a Sonogashira coupling route

Alkynyl versions of cinnamaldehye semicarbazone and their photochromicity

247th National Meeting (2014)

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