Facile synthesis of highly efficient phenyltetraene-based nonlinear optical chromophores for electrooptics.

[reaction: see text] A facile synthetic route has been developed to convert an electron-rich, sterically hindered dialkylaminodienone into a conjugated dialkylaminotrienal with good yield. The derived dialkylaminotetraene-type nonlinear optical chromophores possess an all-trans conformation and can be functionalized with fluoro-dendron to provide proper shape modification for poling. Polymers doped with two examples of these chromophores in high concentrations have been poled to afford ultra-large electrooptic coefficients (r(33)) of 208 and 262 pm/V, respectively, at the measuring wavelength of 1.31 mum.

[1]  Inflation parameters from Gauss-Bonnet braneworld , 2004, astro-ph/0409106.

[2]  Larry R. Dalton,et al.  Importance of intermolecular interactions in the nonlinear optical properties of poled polymers , 2000 .

[3]  A. Jen,et al.  A side-chain dendronized nonlinear optical polyimide with large and thermally stable electrooptic activity , 2004 .

[4]  Larry R. Dalton,et al.  Synthesis and Characterization of Sterically Stabilized Second-Order Nonlinear Optical Chromophores , 1999 .

[5]  Cheng Zhang,et al.  Integration of electro-optic polymer modulators with low-loss fluorinated polymer waveguides. , 2002, Optics letters.

[6]  A. Jen,et al.  Highly Efficient and Thermally Stable Electro‐optic Polymer from a Smartly Controlled Crosslinking Process , 2003 .

[7]  S. Ho,et al.  Organic electro-optic modulator using transparent conducting oxides as electrodes. , 2005, Optics express.

[8]  S. Barlow,et al.  Synthesis and stability studies of conformationally locked 4-(diarylamino)aryl- and 4-(dialkylamino)phenyl-substituted second-order nonlinear optical polyene chromophores , 2003 .

[9]  A. Jen,et al.  Focused Microwave‐Assisted Synthesis of 2,5‐Dihydrofuran Derivatives as Electron Acceptors for Highly Efficient Nonlinear Optical Chromophores , 2003 .

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

[11]  Bruce H. Robinson,et al.  Monte Carlo Statistical Mechanical Simulations of the Competition of Intermolecular Electrostatic and Poling-Field Interactions in Defining Macroscopic Electro-Optic Activity for Organic Chromophore/Polymer Materials† , 2000 .

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

[13]  S. Garner,et al.  Synthesis of Chromophores with Extremely High Electro-optic Activities. 2. Isophorone- and Combined Isophorone−Thiophene-Based Chromophores , 2002 .

[14]  C. C. Teng,et al.  Simple reflection technique for measuring the electro‐optic coefficient of poled polymers , 1990 .

[15]  Jingdong Luo,et al.  Replica-molded electro-optic polymer Mach–Zehnder modulator , 2004 .

[16]  J. Perry,et al.  Relation Between Bond-Length Alternation and Second Electronic Hyperpolarizability of Conjugated Organic Molecules , 1993, Science.

[17]  Mario Bertolotti,et al.  On the measurement of the electro-optic properties of poled side-chain copolymer films with a modified Teng–Man technique , 1999 .

[18]  A. Jen,et al.  Design and synthesis of chromophores and polymers for electro-optic and photorefractive applications , 1997, Nature.

[19]  Larry R. Dalton,et al.  Low Vπ electrooptic modulators from CLD-1 : Chromophore design and synthesis, material processing, and characterization , 2001 .

[20]  R. Twieg,et al.  Synthesis and nonlinearity of triene chromophores containing the cyclohexene ring structure , 1997 .

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

[22]  M. Larciprete,et al.  Measurement of the electro-optic properties of poled polymers at λ=1.55 μm by means of sandwich structures with zinc oxide transparent electrode , 2003 .

[23]  Liang Zuo,et al.  Crystal structure and phase transformation in Ni53Mn25Ga22 shape memory alloy from 20Kto473K , 2005 .

[24]  Larry R. Dalton,et al.  Electric Poling and Relaxation of Thermoset Polyurethane Second-Order Nonlinear Optical Materials: Role of Cross-Linking and Monomer Rigidity , 2001 .

[25]  Larry R. Dalton,et al.  Highly Efficient and Thermally Stable Electro‐Optical Dendrimers for Photonics , 2002 .

[26]  Bruce H. Robinson,et al.  A Novel Lattice-Hardening Process To Achieve Highly Efficient and Thermally Stable Nonlinear Optical Polymers , 2004 .

[27]  Larry R. Dalton,et al.  Nanoscale architectural control and macromolecular engineering of nonlinear optical dendrimers and polymers for electro-optics , 2004 .

[28]  Jingdong Luo,et al.  Design, Synthesis, and Properties of Highly Efficient Side‐Chain Dendronized Nonlinear Optical Polymers for Electro‐Optics , 2002 .

[29]  A. Jen,et al.  A new synthetic approach for nonlinear optical chromophores possessing enhanced thermal stability , 1996 .

[30]  O. A. Shlyakhtin,et al.  Recent progress in cryochemical synthesis of oxide materials , 1999 .

[31]  Mark A. Ratner,et al.  Design, Synthesis, and Properties of Molecule‐Based Assemblies with Large Second‐Order Optical Nonlinearities , 1995 .

[32]  E. Durantini.  Synthesis of Functional Olefins Using the Wittig-Horner Reaction in Different Media , 1999 .

[33]  Larry R. Dalton,et al.  Resonance enhanced THz generation in electro-optic polymers near the absorption maximum , 2004 .

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

[35]  Min-Cheol Oh,et al.  Flexible low-voltage electro-optic polymer modulators , 2003 .

[36]  Seth R. Marder,et al.  Large First Hyperpolarizabilities in Push-Pull Polyenes by Tuning of the Bond Length Alternation and Aromaticity , 1994, Science.