Poly[(4‐N‐ethylene‐N‐ethylamino)‐α‐cyanocinnamate]: A nonlinear optical polymer with a chromophoric mainchain. I. Synthesis and spectral characterization

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Abstract
Poly[(4‐N‐ethylene‐N‐ethylamino)‐α‐cyanocinnamate] was prepared by solution esterification of (4‐N‐ethyl‐N‐(2‐hydroxyethyl) amino)‐α‐Cyanocinnamic acid and by melt transesterification of ethyl (4‐N‐ethyl‐N‐(2‐hydroxyethyl) amino)‐α‐cyanocinnamate. The melt transesterification generally yielded polymer with a number‐average molecular weight of about 10,200 by gel permeation chromatography (GPC) versus polystyrene standards. The polymer was found to be amorphous with a glass transition temperature of about 103°C by differential scanning calorimetry (DSC). The solution esterification generally gave a polymer with a number‐average molecular weight of about 2200 by GPC versus polystyrene standards. This polymer was found to have a glass transition temperature varying between 60 and 90°C by DSC. The infrared (IR) spectrum of the polymer made from both methods were analyzed in detail. The1H‐ and13C‐NMR spectra of the meltsynthesized ethyl cinnamate derivative polymer are consistent with the reported structure.