Design And Synthesis Of 4-Nitro-4'-N,N-di(glycidyl) Aminoazobenzene

Based on the molecule design, a new D- π -A structure nonlinear optical chromophore molecule [4-Nitro-4'-N,N-di(glycidyl) aminoazobenzene (NGDA) ] has been designed . Azobenzene has large nonlinear coefficient and epoxy makes it easy to dope in polymer. The thermal stability should be improved by reacting or crosslinking with other molecules, than the orientation of the chromophores can be fixed in polymer films.4-Nitro-4'-N,N-di(glycidyl) aminoazobenzene has been researched by ZINDO-SOS, and the facts for molecular nonlinear properties have been analyzed by quantum mechanics. Meanwhile, the results such as the equilibrium bond structure, excited states, frontier orbits, second harmonic generation (SHG) and dipole have been give out, which indicate the molecule designed has very good nonlinear optical properties.4-Nitro-4'-N,N-di(glycidyl) aminoazobenzene has been synthesized by N-alkyl and diazotized, the last yield is 56%. The structure of NGDA has been confirmed by analyzed element analysis, MS, ~1HNMR, GPC, FTIR and UV-Vis spectra.The polymer 1 has been synthesized with NGDA and aniline, then the films of polymer 1 on ITO conducted glass have been poled under electric field. The orientation stability of the chromophores in films was studied by UV-vis spectrum measurement and decreasing and moving to long wave of their absorption peaks have been observed after poled. Then some experiential principals for select theparameters of poled have been summarized by many experiments.A network polymer was synthesized from toluene-2,4-di-iso-cyanate and polymer 1 by crosslinking reaction for better orientation thermal stability of organic non-linear optical films. However, the relaxation of the poled film was not observed after 5 days by poling and crosslinking for lh at 140°C. Another, a new organic and inorganic hybrid has been synthesized by doping NGDA into silica-sol dried and poled under electronic field. Results show that the transparence of films has improved. But there are some small cracks appeared with large doping, it wishes to be ameliorated by bonded the chromophores into inorganic network in future research.