Dendronized tricyanopyrroline‐based chromophores in nonlinear optical active host polymer

Abstract

We synthesized new nonlinear optical (NLO) chromophores containing a 3,5‐bis(3,5‐bisbenzyloxy‐benzyloxy)‐benzoate dendron. Tricyanopyrroline (TCP)‐based chromophores were designed and prepared by virtue of its strong electron withdrawing property. A soluble polyimide containing 6‐({4‐[2‐(1‐allyl‐4‐cyano‐5‐dicyanomethylene‐2‐oxo‐2,5‐dihydro‐1H‐pyrrol‐3‐yl)‐vinyl]‐phenyl}‐butyl‐amino)‐hexanoyl group in the side chain was also prepared as an NLO active host polymer. A benzoate dendron was tethered at two different binding positions of the chromophore to yield two different guest molecules. Thin‐film composites of these dendronized chromophores dissolved in the NLO active polyimide host were employed to fabricate the electro‐optic (EO) samples. The EO properties of new NLO polyimides containing dendronized chromophores were compared with those of the sample with nondendronized plain chromophores. The effect of a bulky dendron on the EO properties was investigated using an in situ reflection technique. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 5064–5076, 2008

Synthesis and electro-optic properties of novel X-type polyester containing dioxynitrobenzylidenecyanoacetate with highly enhanced thermal stability of dipole alignment

“…A potential NLO polymer must contain highly polarizable conjugated electronic systems constituted by electron donor and acceptor moieties, and has to be mechanically very strong and thermally stable with a high glass-transition temperature (T g ). In the synthesis of NLO polymers for electro-optic device applications, stabilization of electrically induced dipole alignment is one of important considerations, and several approaches to minimize the randomization have been proposed, such as the use of cross-linked systems [13][14][15][16][17][18][19][20][21], the utilization of polymers with high T g polyimides [22][23][24][25][26][27][28][29], and H-shape polymers [30]. Various polyesters with NLO chromophores in the main chain [31,32] or side chain [33,34] have been prepared and their NLO properties studied.…”

Synthesis and Nonlinear Optical Properties of Novel Polyester with Enhanced Second Harmonic Generation Thermal Stability

“…In the developments of NLO polymers for electro-optic device applications, stabilization of electrically induced dipole alignment is one of important criteria; in this context, two approaches have been proposed to minimize the randomization of dipole alignment, namely the use cross-linking method [7][8][9][10] and the utilization of high T g polymers such as polyimides. [11][12][13][14][15][16] Various polyesters with NLO chromophores in the main chain 17 or in side chain [18][19] have been prepared and their properties studied. In general, main-chain NLO polymers have good thermal stability of dipole alignments, but they often do not dissolve in organic solvents, and their intractability make them unusable to fabricate stable films.…”

Synthesis and Properties of Novel Y-type Nonlinear Optical Polyester Containing Dioxynitroazobenzene Group with Enhanced Thermal Stability of Dipole Alignment

“…In the developments of NLO polymers for electro-optic device applications, stabilization of electrically induced dipole alignment is one of important considerations; in this context, two approaches to minimize the randomization have been proposed, namely the use of cross-linked systems [5][6][7][8] and the utilization of polymers with high glass transition temperature (T g ) such as polyimides. [9][10][11][12][13][14] Various polyesters with NLO chromophores in the main chain 15,16 or side chain 17,18 have been prepared and their NLO properties studied. Polyesters with amino-sulfone azobenzene chromophores in the main chain generate strong and stable reversible birefringence.…”