Synthesis and characterization of a new disubstituted polyacetylene containing indolylazo moieties in side chains

A new disubstituted polyacetylene with indolylazo moieties in its side chains (9) was synthesized by a post functionalization strategy, which was difficult, or perhaps impossible, to obtain from the direct polymerization of its corresponding monomer. The polymer is soluble in common solvents and thermally stable. The polymer shows good optical transparency with an absorption maximum at 393 nm and a band edge at ∼530 nm. Its poled film exhibits a resonant d33 value of 17.9 pm/V and its optical nonlinearity is resistant to thermal decay at up to 147 °C. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 5672–5681, 2006

[1]  E. Yashima,et al.  Helicity induction on a poly(phenylacetylene) bearing a phosphonate residue by chiral dendrons , 2004 .

[2]  Craig J. Hawker,et al.  The Convergence of Synthetic Organic and Polymer Chemistries , 2005, Science.

[3]  B. Tang,et al.  Liquid‐crystalline and light‐emitting polyacetylenes , 2003 .

[4]  Eiji Yashima,et al.  Atomic force microscopy observation of a helical poly(phenylacetylene) bearing aza-18-crown-6 ether pendants induced by amino acids , 2004 .

[5]  Jingdong Luo,et al.  Large electro-optic activity and low optical loss derived from a highly fluorinated dendritic nonlinear optical chromophore. , 2002, Chemical communications.

[6]  K. Cheuk,et al.  Syntheses, hydrogen-bonding interactions, tunable chain helicities, and cooperative supramolecular associations and dissociations of poly(phenylacetylene)s bearing L-valine pendants: Toward the development of proteomimetic polyenes , 2003 .

[7]  C. Ober,et al.  Liquid crystalline and rigid-rod networks , 1993 .

[8]  B. Freeman,et al.  Synthesis and Properties of Poly(diphenylacetylenes) Having Hydroxyl Groups , 2005 .

[9]  J. Qin,et al.  Second-order nonlinear optical property of polyphosphazenes containing charge-transporting agents and indole-based chromophore , 2005 .

[10]  Larry R. Dalton,et al.  Polymer-based optical waveguides: Materials, processing, and devices , 2002 .

[11]  Jingui Qin,et al.  Polyphophazene containing indole-based dual chromophores: Synthesis and nonlinear optical characterization , 2002 .

[12]  Larry R. Dalton,et al.  Progress toward Device-Quality Second-Order Nonlinear Optical Materials. 4. A Trilink High μβ NLO Chromophore in Thermoset Polyurethane: A “Guest−Host” Approach to Larger Electrooptic Coefficients , 2001 .

[13]  J. Vicente,et al.  Synthesis, characterization, and metal complexes of polyacetylenes with pendant 2,2′‐bipyridyl groups , 2005 .

[14]  Donald M. Burland,et al.  SECOND-ORDER NONLINEARITY IN POLED-POLYMER SYSTEMS , 1994 .

[15]  Zhang,et al.  Low (Sub-1-volt) halfwave voltage polymeric electro-optic modulators achieved by controlling chromophore shape , 2000, Science.

[16]  Nakjoong Kim,et al.  %Synthesis and Properties of Photorefractive Polymers Containing Indole-Based Multifunctional Chromophore as a Pendant Group , 2000 .

[17]  Jingui Qin,et al.  A New Postfunctional Approach To Prepare Second-Order Nonlinear Optical Polyphophazenes Containing Sulfonyl-Based Chromophore , 2004 .

[18]  Hong Ma,et al.  Functional Dendrimers for Nonlinear Optics , 2001 .

[19]  A. Jen,et al.  Highly efficient and thermally stable nonlinear optical dendrimer for electrooptics. , 2001, Journal of the American Chemical Society.

[20]  Han Peng,et al.  Conjugated Polymers with Linear and Hyperbranched Structures and Advanced Materials Properties , 2004 .

[21]  Yongqiang Dong,et al.  Functionalization of Disubstituted Polyacetylenes through Polymer Reactions: Syntheses of Functional Poly(1-phenyl-1-alkyne)s , 2006 .

[22]  E. Yashima,et al.  Convenient synthesis of fully and partially deuterated stereoregular poly(phenylacetylene)s bearing a carboxy pendant and helicity induction on the polymers with chiral amines and its memory , 2004 .

[23]  Jingui Qin,et al.  Synthesis of novel poly{methyl-[3-(9-indolyl)propyl]siloxane}-based nonlinear optical polymers via postfunctionalization , 2005 .

[24]  B. Tang,et al.  Mechanical properties of substituted polyacetylenes , 1986 .

[25]  Ben Zhong Tang,et al.  Facile Synthesis, Large Optical Nonlinearity, and Excellent Thermal Stability of Hyperbranched Poly(aryleneethynylene)s Containing Azobenzene Chromophores , 2006 .

[26]  J. Vohlídal,et al.  Polymerization of substituted acetylenes by various rhodium catalysts: Comparison of catalyst activity and effect of additives , 2005 .

[27]  Katsuhiro Maeda,et al.  Detection and amplification of chirality by helical polymers. , 2004, Chemistry.

[28]  G. Ruggeri,et al.  Synthesis and characterization of different poly(1-vinylindole)s for photorefractive materials , 2001 .

[29]  Joerg Heber,et al.  Broadband Modulation of Light by Using an Electro-Optic Polymer , 2002, Science.

[30]  Ian D. Williams,et al.  Optically active polyacetylene: Synthesis and helical conformation of a poly(phenylacetylene) carrying L‐alanyl‐L‐alanine pendants , 2005 .

[31]  J. Vohlídal,et al.  Controlled and Living Polymerizations Induced with Rhodium Catalysts. A Review , 2003 .

[32]  T. Satoh,et al.  Metal‐cation‐induced chiroptical switching for poly(phenylacetylene) bearing a macromolecular ionophore as a graft chain , 2005 .

[33]  Fumio Sanda,et al.  Polymerization of substituted phenylacetylenes with a novel, water‐soluble Rh–vinyl complex in water , 2004 .

[34]  T. Masuda,et al.  Synthesis of chiral polyacetylenes carrying amino acids and azobenzenes and transformation of the higher order structure by photoirradiation , 2004 .

[35]  J. Qin,et al.  Synthesis and characterization of indole-containing chromophores for second-order nonlinear optics. , 2006, The journal of physical chemistry. B.

[36]  J. Qin,et al.  Second-order nonlinear optical property of polysiloxane containing indole-based multifunctional chromophore , 2003 .