Novel chromophore with tricyanocyclopentenone electronic acceptor and its application in organic EO polymers

Novel organic second nonlinear optical chromophoreGL-1 based on tricyanocyclopentenone (TCNP) electronic acceptorgroup were designed and synthesized in this paper. The structure of chromophoreGL-1 is characterized by mass spectrum and nuclear magnetic resonance spectroscopy. ChromophoreFTC based on traditional tricyanofuran (TCF) electronic acceptorwas also prepared as the contrast. Their delocalized energy levels were estimated by UV–Vis spectra. Their thermal properties were studied by thermogravimetric analysis. Obviously, chromophoreGL-1 showed lower delocalized energy levels and higher thermal decomposition temperature (just about 286 °C). Electro-optics polymers prepared based on chromophoreGL-1 showed the largest SHG coefficients of about 119 pm/V, which was about two times higher than chromophoreFTC (about 68 pm/V). These advantages of chromophoreGL-1 are attributed to the improvement of first order hyperpolarizabilityand the attenuatation of intermolecular dipole interaction by the introduction of tricyanocyclopentenone electronic acceptor. And in another word, tricyanocyclopentenone electronic acceptormay be a promising way to drastically change the nonlinear opticalfeatures of the titled compounds and show a direction of designing new electron acceptorin the field of nonlinear opticalmaterials.