Abstract
Abstract The photochromic and thermochromic properties in various classes of the Schiff bases of salicylaldehydes with benzylamine and thenylamine were investigated in the crystalline state at various temperatures. The reaction involved is an intramolecular hydrogen transfer where the enol-keto tautomeric species are in equilibrium. In all of the series studied, the salicylaldimino group that takes part in the reaction has the same geometry in the crystalline state: a strong intramolecular hydrogen bond that “locks” it into the planar configuration. It is suggested that what determines thermochromic or photochromic behaviour is not planarity or non planarity, respectively, of the molecules, but rather the electron density of the lone pair of the imino nitrogen atom.
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