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

被引:91
作者
Luo, JD
Cheng, YJ
Kim, TD
Hau, S
Jang, SH
Shi, ZW
Zhou, XH
Jen, AKY [1 ]
机构
[1] Univ Washington, Dept Mat Sci & Engn, Seattle, WA 98195 USA
[2] Univ Washington, Dept Chem, Seattle, WA 98195 USA
关键词
D O I
10.1021/ol060178b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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/N, respectively, at the measuring wavelength of 1.31 mu m.
引用
收藏
页码:1387 / 1390
页数:4
相关论文
共 45 条
  • [1] Integration of electro-optic polymer modulators with low-loss fluorinated polymer waveguides
    Ahn, SW
    Steier, WH
    Kuo, YH
    Oh, MC
    Lee, HJ
    [J]. OPTICS LETTERS, 2002, 27 (23) : 2109 - 2111
  • [2] From molecules to opto-chips: organic electro-optic materials
    Dalton, LR
    Steier, WH
    Robinson, BH
    Zhang, C
    Ren, A
    Garner, S
    Chen, AT
    Londergan, T
    Irwin, L
    Carlson, B
    Fifield, L
    Phelan, G
    Kincaid, C
    Amend, J
    Jen, A
    [J]. JOURNAL OF MATERIALS CHEMISTRY, 1999, 9 (09) : 1905 - 1920
  • [3] Synthesis of functional olefins using the Wittig-Horner reaction in different media
    Durantini, EN
    [J]. SYNTHETIC COMMUNICATIONS, 1999, 29 (23) : 4201 - 4222
  • [4] Synthesis and nonlinearity of triene chromophores containing the cyclohexene ring structure
    Ermer, S
    Lovejoy, SM
    Leung, DS
    Warren, H
    Moylan, CR
    Twieg, RJ
    [J]. CHEMISTRY OF MATERIALS, 1997, 9 (06) : 1437 - 1442
  • [5] PENTADIENYL CARBOXAMIDE DERIVATIVES AS ANTAGONISTS OF PLATELET-ACTIVATING FACTOR
    GUTHRIE, RW
    KAPLAN, GL
    MENNONA, FA
    TILLEY, JW
    KIERSTEAD, RW
    MULLIN, JG
    LEMAHIEU, RA
    ZAWOISKI, S
    ODONNELL, M
    CROWLEY, H
    YAREMKO, B
    WELTON, AF
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (08) : 1820 - 1835
  • [6] A novel lattice-hardening process to achieve highly efficient and thermally stable nonlinear optical polymers
    Haller, M
    Luo, JD
    Li, HX
    Kim, TD
    Liao, Y
    Robinson, BH
    Dalton, LR
    Jen, AKY
    [J]. MACROMOLECULES, 2004, 37 (03) : 688 - 690
  • [7] Synthesis of new electrooptic chromophores and their structure-property relationship
    He, MQ
    Leslie, T
    Garner, S
    DeRosa, M
    Cites, J
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2004, 108 (25) : 8731 - 8736
  • [8] Synthesis of chromophores with extremely high electro-optic activities. 2. Isophorone- and combined isophorone-thiophene-based chromophores
    He, MQ
    Leslie, TM
    Sinicropi, JA
    Garner, SM
    Reed, LD
    [J]. CHEMISTRY OF MATERIALS, 2002, 14 (11) : 4669 - 4675
  • [9] JEN AKY, 2005, P SOC PHOTO-OPT INS, V5935, P49
  • [10] Very large electro-optic coefficients from in situ generated side-chain nonlinear optical polymers -: art. no. 071109
    Kang, JW
    Kim, TD
    Luo, J
    Haller, M
    Jen, AKY
    [J]. APPLIED PHYSICS LETTERS, 2005, 87 (07)