Abstract
A number of mixtures of halosquaraines have been synthesized by co-reacting mixtures of N,N-dimethylaniline and N,N-dimethylhaloaniline with dibutyl squarate in water-saturated 1-butanol. Yield decreases as the concentration of N,N-dimethylhaloaniline increases and this decrease is attributable to the low reactivity of N,N-dimethylhaloaniline. This low reactivity is also revealed in the lower than expected halogen incorporation in all the mixtures studied. The chemical composition of each mixture was studied by high-resolution proton NMR spectroscopy and mass spectrometry. The merit of these two techniques in the identification and quantification of individual squaraines in the mixtures is presented and discussed. The xerographic properties of each mixture were studied by xerographic photodischarge technique in bilayer photoreceptor devices; improvement in photosensitivity is observed for squaraine mixtures synthesized from N,N-dimethylaniline (DMA) and 3-fluoro-N,N-dimethylaniline (3-FDMA). At a DMA/3-FDMA ratio of 75/25, the fluorosquaraine composition synthesized exhibits photosensitivity similar to the pure fluorosquaraine synthesized from 3-FDMA. The yield of such a composition is 30%, an improvement of 11% from the pure fluorosquaraine synthesized from 3-FDMA.
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