Epoxy-Based Nonlinear Optical Polymers Functionalized with Tricyanovinyl Chromophores

Two types of new nonlinear optical polymers have been synthesized by postreaction of an epoxy-based polymer prepared from the diglycidyl ether of bisphenol A and aniline. The new polymers DGEBA-AZO-TCV and DGEBA-AN-TCV were synthesized by azo coupling of the epoxy polymer with 4-(tricyanovinyl)aniline and by reacting the epoxy polymer with tetracyanoethylene, respectively. Using an azo coupling reaction to functionalize the polymer allows introduction of the tricyanovinyl (TCV) group and extension of the conjugation length to take place in a single-step reaction. In both synthetic routes, TCV groups are introduced at the last stage of the polymer preparation, thus preventing the exposure of the TCV chromophores to harsh reaction conditions. The d 33 values for polymers DGEBA-AN-TCV and DGEBA-AZO-TCV were determined to be 27 and 66 pm/V at 1.542 μm, respectively, after corona poling. The two polymers retained 65% and 83% of the initial d 33 values after they had been heated at 80 °C for 1000 h.