Synthesis of functionalized organic second-order nonlinear optical chromophores for electrooptic applications

被引:55
作者
Thayumanavan, S
Mendez, J
Marder, SR [1 ]
机构
[1] CALTECH, Beckman Inst, Pasadena, CA 91125 USA
[2] CALTECH, Jet Prop Lab, Pasadena, CA 91125 USA
[3] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
关键词
D O I
10.1021/jo981707v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The design and syntheses of functionalized second-order nonlinear optical chromophores, suitable for covalent incorporation into functionalized high-performance polymers, are described. The chromophores with hydroxy alkyl functionality have diarylamino groups as the donor moiety and a styryl thiophene moiety as the conjugated bridge. The triarylamine parts of the molecules were synthesized using palladium-catalyzed C-N bond forming reactions. The conjugated bridge was assembled using the Wittig reaction. The acceptor groups were installed in the last steps of the syntheses.
引用
收藏
页码:4289 / 4297
页数:9
相关论文
共 59 条
  • [1] Chromophores with strong heterocyclic acceptors: A poled polymer with a large electro-optic coefficient
    Ahlheim, M
    Barzoukas, M
    Bedworth, PV
    BlanchardDesce, M
    Fort, A
    Hu, ZY
    Marder, SR
    Perry, JW
    Runser, C
    Staehelin, M
    Zysset, B
    [J]. SCIENCE, 1996, 271 (5247) : 335 - 337
  • [2] [Anonymous], POLED POLYM THEIR AP
  • [3] LARGE AND STABLE NONLINEAR-OPTICAL EFFECTS OBSERVED FOR A POLYIMIDE COVALENTLY INCORPORATING A NONLINEAR-OPTICAL CHROMOPHORE
    BECKER, MW
    SAPOCHAK, LS
    GHOSEN, R
    XU, CZ
    DALTON, LR
    SHI, YQ
    STEIER, WH
    JEN, AKY
    [J]. CHEMISTRY OF MATERIALS, 1994, 6 (02) : 104 - 106
  • [4] Synthesis and relative thermal stabilities of diphenylamino- vs piperidinyl-substituted bithiophene chromophores for nonlinear optical materials
    Bedworth, PV
    Cai, YM
    Jen, A
    Marder, SR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) : 2242 - 2246
  • [5] Large quadratic hyperpolarizabilities with donor-acceptor polyenes exhibiting optimum bond length alternation: Correlation between structure and hyperpolarizability
    BlanchardDesce, M
    Alain, V
    Bedworth, PV
    Marder, SR
    Fort, A
    Runser, C
    Barzoukas, M
    Lebus, S
    Wortmann, R
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (07) : 1091 - 1104
  • [6] Intramolecular charge transfer and enhanced quadratic optical non-linearities in push-pull polyenes
    BlanchardDesce, M
    Alain, V
    Midrier, L
    Wortmann, R
    Lebus, S
    Glania, C
    Kramer, P
    Fort, A
    Muller, J
    Barzoukas, M
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1997, 105 (2-3) : 115 - 121
  • [7] Bosshard C., 1995, Organic nonlinear optical materials, P256
  • [8] Chemia D. S., 1987, Nonlinear optical properties of organic molecules and crystals
  • [9] FACILE APPROACH TO NONLINEAR-OPTICAL SIDE-CHAIN AROMATIC POLYIMIDES WITH LARGE 2ND-ORDER NONLINEARITY AND THERMAL-STABILITY
    CHEN, TA
    JEN, AKY
    CAI, YM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) : 7295 - 7296
  • [10] Two-step synthesis of side-chain aromatic polyimides for second-order nonlinear optics
    Chen, TA
    Jen, AKY
    Cai, YM
    [J]. MACROMOLECULES, 1996, 29 (02) : 535 - 539