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Design and Synthesis of Soluble Thermally Stable Nonlinear Optical Chromophores Based on the Dicyanomethylenepyran Moiety

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Abstract

For several years we have been developing polyimide-based electro-optic materials based on commercially available components. In 1992, we described a proof-of-principle all-polyimide triple stack Mach-Zehnder modulator using DCM (4-(dicyanomethylene)-2-methyl-6-(p-di-methylaminostyryl)-4H-pyran) in Amoco Ultradei 3112 polyimide as the active core layer with Amoco Ultradei 4212 polyimide cladding layers.1 During the course of our work we found that some commercial preparations of DCM contained a significant amount of a less soluble, more thermally stable impurity which we identified as the bis condensation product arising from the synthesis of DCM itself.2 This impurity, DAD, and several analogs were synthesized, and their physical and NLO properties were investigated.3 Figure 1 shows the synthetic scheme used for their preparation.

© 1995 Optical Society of America

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