Second order nonlinear optical networks with excellent poling stability from a new trifunctional thiophene based chromophore

Two new trifunctional thiophene based dyes suited for crosslinking were synthesised from the same structural core, i.e. 4-[[5-[(4-nitrophenyl)azo]-2-thienyl]azo]benzenamine. Crystal structure and second order nonlinear optical properties were determined on a related difunctional dye that can be considered as a representative and simplified model of the trifunctional compounds, determining on it the mu beta value of 4950 x 10(-48) esu (6111 x 10(-80) C-2 m(4) V-2). The presence of three acrylic or hydroxyl functional groups in the dyes allowed to incorporate the chromophoric fragment into two different kinds of crosslinked materials possessing "frozen" long-lasting dipole order. The traditional guest-host approach used for one of them was exceeded by covalently anchoring the chromophore to a functionalised polymer in a three-dimensional unique network. In this way a promising NLO active material was obtained. The value of the d(33) coefficient (determined by SHG measurement using the Maker fringe technique) was 11 pm/V for the poled/crosslinked film. Very good thermal and temporal stability of the chromophore poling-induced dipole alignment was attained. (C) 2008 Elsevier B.V. All rights reserved.