The facile synthesis and optical nonlinearity of hyperbranched polyaspartimides with azobenzene dyes

Dyes and Pigments

Volumn 82, Issue 1, 2009, Pages 31-39

  Tsai, Cheng Che ^a   Chao, Tsung Yi ^a   Lin, Hsun Lien ^a   Liu, Yue Hua ^a   Chang, Huey Ling ^b   Liu, Ying Ling ^c   Jeng, Ru Jong ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

^b NATIONAL CHIN YI UNIVERSITY OF TECHNOLOGY   (Taiwan)

^c CHUNG YUAN CHRISTIAN UNIVERSITY   (Taiwan)

Author keywords

Azobenzene dye; Electro optical coefficient; Hyperbranched polymer; Michael addition reaction; Nonlinear optical; Polyaspartimides

Indexed keywords

ADDITION REACTIONS; AMINES; CHEMICAL REACTIONS; DENDRIMERS; ETHANE; FLUORINE; NONLINEAR OPTICS; ORGANIC COMPOUNDS; ORGANIC POLYMERS; ORGANIC SOLVENTS; POLYMERS; STRUCTURAL OPTIMIZATION; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL); THREE DIMENSIONAL;

AZOBENZENE DYE; ELECTRO-OPTICAL COEFFICIENT; HYPERBRANCHED POLYMER; MICHAEL ADDITION REACTION; NONLINEAR OPTICAL; POLYASPARTIMIDES;

POLYMER BLENDS;

AZO DYE; CATALYST; CHEMICAL REACTION; SOLUBILITY; SOLVENT;

EID: 60449110494     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2008.10.013     Document Type: Article

References (63)

1. Haller M., Luo J.D., Li H.X., Kim T.D., Liao Y., Robinson B., et al. A novel lattice-hardening process to achieve highly efficient and thermally stable nonlinear optical polymers. Macromolecules 37 3 (2004) 688-690
2. Chen L., Qian G., Gui Y., Jin X., Wang Z., and Wang M.J. Hybrid materials covalently incorporated with isophorone-based dyes through sol-gel process for nonlinear optical applications. Journal of Physical Chemistry B 110 39 (2006) 19176-19182
3. Zhang C., Dalton L.R., Oh M.C., Zhang H., and Steier W. Low Vπ electrooptic modulators from CLD-1: chromophore design and synthesis, material processing, and characterization. Chemistry of Materials 13 9 (2001) 3043-3050
4. Verbiest T., Houbrechts S., Kauranen M., Clays K., and Persoons A. Second-order nonlinear optical materials: recent advances in chromophore design. Journal of Materials Chemistry 7 11 (1997) 2175-2189
5. Zhang C.Z., Lu C., Zhu J., Lu G.Y., Wang X., Shi Z.W., et al. The second-order nonlinear optical materials with combined nonconjugated D-π-A units. Chemistry of Materials 18 26 (2006) 6091-6093
6. Dalton L.R., Harper A., Ren A., Wang W., Todorova G., Chen J., et al. Polymeric electro-optic modulators: from chromophore design to integration with semiconductor very large scale integration electronics and silica fiber optics. Industrial and Engineering Chemistry Research 38 1 (1999) 8-33
7. Ma H., Chen B., Sassa T., Dalton L.R., and Jen A.K.Y. Highly efficient and thermally stable nonlinear optical dendrimer for electrooptics. Journal of the American Chemical Society 123 5 (2001) 986-987
8. Ma H., and Jen A.K.Y. Functional dendrimers for nonlinear optics. Advanced Materials 13 15 (2001) 1201-1205
9. Do J.Y., Park S.K., Ju J.J., Park S., and Lee M.H. Electro-optic materials: hyperbranched chromophores attached linear polyimide and dendritic polyesters. Polymers for Advanced Technologies 16 2-3 (2005) 221-226
10. Robinson B.H., and Dalton L.R. 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. Journal of Physical Chemistry A 104 20 (2000) 4785-4795
11. Sullivan P.A., Akelaitis A.J.P., Lee S.K., McGrew G., Lee S.K., Choi D.H., et al. Novel dendritic chromophores for electro-optics: influence of binding mode and attachment flexibility on electro-optic behavior. Chemistry of Materials 18 2 (2006) 344-351
12. Zhu Z., Li Z., Tan Y., Li Z., Li Q., Zeng Q., et al. New hyperbranched polymers containing second-order nonlinear optical chromophores: synthesis and nonlinear optical characterization. Polymer 47 23 (2006) 7881-7888
13. Ma H., Wu J., Herguth P., Chen B., and Jen A.K.Y. A novel class of high-performance perfluorocyclobutane-containing polymers for second-order nonlinear optics. Chemistry of Materials 12 5 (2000) 1187-1189
14. Do J.Y., and Ju J.J. Polyester dendrimers carrying NLO chromophores: synthesis and optical characterization. Macromolecular Chemistry and Physics 206 13 (2005) 1326-1331
15. Fréchet J.M.J., Henmi M., Gitsov I., Aoshima S., Leduc M.R., and Grubbs R.B. Self-condensing vinyl polymerization: an approach to dendritic materials. Science 269 (1995) 1080-1083
16. Li Z., Qin A., Lam J.W.Y., Dong Y., Dong Y., Ye C., et al. Facile synthesis, large optical nonlinearity, and excellent thermal stability of hyperbranched poly(aryleneethynylene)s containing azobenzene chromophores. Macromolecules 39 4 (2006) 1436-1442
17. Hecht S., and Fréchet J.M.J. Dendritic encapsulation of function. Angewandte Chemie International Edition 40 1 (2001) 74-91
18. Ma H., Liu S., Luo J., Suresh S., Liu L., Kang S.H., et al. Highly efficient and thermally stable electro-optical dendrimers for photonics. Advanced Functional Materials 12 9 (2002) 565-574
19. 2 type polycondensation with substitution effect. Polymer 47 4 (2006) 1473-1479
20. Chang H.L., Chao T.Y., Yang C.C., Dai S.A., and Jeng R.J. Second-order nonlinear optical hyperbranched polymers via facile ring-opening addition reaction of azetidine-2,4-dione. European Polymer Journal 43 9 (2007) 3988-3996
21. Xie J., Deng X., Cao Z., Shen Q., Zhang W., and Shi W. Synthesis and second-order nonlinear optical properties of hyperbranched polymers containing pendant azobenzene chromophores. Polymer 48 20 (2007) 5988-5993
22. Xie J., Hu L., Shi W., Deng X., Cao Z., and Shen Q. Synthesis and nonlinear optical properties of hyperbranched polytriazole containing second-order nonlinear optical chromophores. Journal of Polymer Science Part B: Polymer Physics 46 12 (2008) 1140-1148
23. Jeng R.J., Chang C.C., Chen C.P., Chen C.T., and Su W.C. Thermally stable crosslinked NLO materials based on maleimides. Polymer 44 1 (2003) 143-155
24. Jeng R.J., Hung W.Y., Chen C.P., and Hsiue G.H. Organic/inorganic NLO materials based on reactive polyimides and a bulky alkoxysilane dye via sol/gel process. Polymers for Advanced Technologies 14 1 (2003) 66-75
25. Lu J., and Yin J. Synthesis and characterization of photocrosslinkable, side-chain, second-order nonlinear optical poly(ester imide)s with great film-forming ability and long-term dipole orientation stability. Journal of Polymer Science Part A: Polymer Chemistry 41 2 (2003) 303-312
26. Bell V.L., and Young P.R. Isomeric bismaleimides and polyaspartimides. Journal of Polymer Science Part A: Polymer Chemistry 24 10 (1986) 2647-2655
27. Wu C.S., Liu Y.L., and Chiu Y.S. Synthesis and characterization of new organosoluble polyaspartimides containing phosphorus. Polymer 43 6 (2002) 1773-1779
28. Liaw D.J., Liaw B.Y., and Chen J.J. Synthesis and characterization of new soluble polyaspartimides derived from bis(3-ethyl-5-methyl-4-maleimidophenyl)-methane and various diamines. Polymer 42 3 (2001) 867-872
29. Tungare A.V., and Martin G.C. Analysis of the curing behavior of bismaleimide resins. Journal of Applied Polymer Science 46 7 (1992) 1125-1135
30. 15N NMR investigation. Macromolecules 31 20 (1998) 6776-6782
31. 2 monomer containing a crown ether and two paraquat moieties. Journal of the American Chemical Society 126 45 (2004) 14738-14739
32. 2 monomers. Macromolecules 38 4 (2005) 1131-1140
33. 2 monomer and postpolymerization modification. Macromolecules 38 21 (2005) 8657-8663
34. 2B monomers. Macromolecules 38 2 (2005) 297-306
35. 3 approach. Macromolecules 35 14 (2002) 5372-5381
36. 3 monomer system. Journal of Polymer Science Part A: Polymer Chemistry 42 7 (2004) 1735-1744
37. Liu Y.L., Tsai S.H., Wu C.S., and Jeng R.J. Preparation and characterization of hyperbranched polyaspartimides from bismaleimides and triamines. Journal of Polymer Science Part A: Polymer Chemistry 42 23 (2004) 5921-5928
38. Saadeh H., Gharavi A., Tu D., and Yu L.P. Polyimides with a diazo chromophore exhibiting high thermal stability and large electrooptic coefficients. Macromolecules 30 18 (1997) 5403-5407
39. Balcerzak E.S., Grabiec E., Sek D., and Miniewicz A. New azobenzene chromophores as monomers for synthesis of polyesters. Polymer Journal 35 (2003) 851-858
40. Mandal B.K., Jeng R.J., Kumar J., and Tripathy S.K. New photocrosslinkable polymers for second-order nonlinear optical processes. Macromolecular Rapid Communications 12 11 (1991) 607-612
41. Chang H.L., Lin H.L., Wang Y.C., Dai S.A., Su W.C., and Jeng R.J. Thermally stable NLO poly(amide-imide)s via sequential self-repetitive reaction. Polymer 48 7 (2007) 2046-2055
42. Teng C.C., and Man H.T. Simple reflection technique for measuring the electro-optic coefficient of poled polymers. Applied Physics Letters 56 18 (1990) 1734-1737
43. Shi W., Fang C.S., Pan Q.W., Gu Q.T., Xu D., Wei H.Z., et al. Measurement of the optical transmission modes and losses of the poled guest-host polymer NAEC/PEK-c planar waveguides. Optics and Lasers in Engineering 33 1 (2000) 21-28
44. Shi W., Fang C.S., Sui Y., Yin J., Pan Q.W., Gu Q.T., et al. Poling optimization and optical loss measurement of the polyetherketone polymer films. Solid State Communications 116 2 (2000) 67-71
45. Shi W., Fang C.S., Sui Y., Yin J., Pan Q.W., Gu Q.T., et al. Thermal stability and transmission losses of the poled polyimide side-chain thin films. Optics Communications 183 1-4 (2000) 299-306
46. Liu Y.L., Jeng R.J., and Chiu Y.S. Triphenylphosphine oxide-based bismaleimide and poly(bismaleimide): synthesis, characterization, and properties. Journal of Polymer Science Part A: Polymer Chemistry 39 10 (2001) 1716-1725
47. Borah J., Mahapatra S.S., Saikia D., and Karak N. Physical, thermal, dielectric and chemical properties of a hyperbranched polyether and its linear analog. Polymer Degradation and Stability 91 12 (2006) 2911-2916
48. Vogtle F., Gestermann S., Hesse R., Schwierz H., and Windisch B.F. Functional dendrimers. Progress in Polymer Science 25 7 (2000) 987-1041
49. Voit B. New developments in hyperbranched polymers. Journal of Polymer Science Part A: Polymer Chemistry 38 14 (2000) 2505-2525
50. Sendijarevic I., McHugh A.J., Markoski L.J., and Moore J.S. Eliminating variations in elemental composition in studies on the physical properties of linear to hyperbranched etherimide copolymers. Macromolecules 34 25 (2001) 8811-8813
51. Sui Y., Liu Y.G., Yin J., Gao J., Zhu Z.K., Huang D.Y., et al. Study on side-chain second-order nonlinear optical polyimides based on novel chromophore-containing diamine. 1. Synthesis and characterization. Journal of Polymer Science Part A: Polymer Chemistry 37 23 (1999) 4330-4336
52. Stutz H. The glass temperature of dendritic polymers. Journal of Polymer Science Part B: Polymer Physics 33 3 (1995) 333-340
53. Sunder A., Bauer T., Mülhaupt R., and Frey H. Synthesis and thermal behavior of esterified aliphatic hyperbranched polyether polyols. Macromolecules 33 4 (2000) 1330-1337
54. Kwak G., and Masuda T. Synthesis, characterization and optical properties of a novel si-containing σ-π-conjugated hyperbranched polymer. Macromolecular Rapid Communications 23 1 (2002) 68-72
55. Sun M., and Bo Z. Tuning the optical properties of hyperbranched polymers through the modification of the end groups. Journal of Polymer Science Part A: Polymer Chemistry 45 1 (2007) 111-124
56. Song N., Men L., Gao J.P., Bai Y., Beaudin A.M.R., Yu G., et al. Cross-linkable zwitterionic polyimides with high electrooptic coefficients at telecommunication wavelengths. Chemistry of Materials 16 19 (2004) 3708-3713
57. Luo J.D., Haller M., Li H.X., Tang H.Z., and Jen A.K.Y. A side-chain dendronized nonlinear optical polyimide with large and thermally stable electrooptic activity. Macromolecules 37 2 (2004) 248-250
58. Bai Y.W., Song N.H., Gao J.P., Sun X., Wang X.M., Yu G.M., et al. A new approach to highly electrooptically active materials using cross-linkable, hyperbranched chromophore-containing oligomers as a macromolecular dopant. Journal of the American Chemical Society 127 7 (2005) 2060-2061
59. Tsutsumi N., Moridhima M., and Sakai W. Nonlinear optical (NLO) polymers. 3. NLO polyimide with dipole moments aligned transverse to the imide linkage. Macromolecules 31 22 (1998) 7764-7769
60. Clays K., and Coe B.J. Design strategies versus limiting theory for engineering large second-order nonlinear optical polarizabilities in charged organic molecules. Chemistry of Materials 15 3 (2003) 642-648
61. Barto R.R., Frank C.W., Bedworth P.V., Taylor R.E., Anderson W.W., Ermer S., et al. Bonding and molecular environment effects on near-infrared optical absorption behavior in nonlinear optical monoazo chromophore-polymer materials. Macromolecules 39 22 (2006) 7566-7577
62. Chen C.P., Huang G.S., Jeng R.J., Chou C.C., Su W.C., and Chang H.L. Low loss second-order non-linear optical crosslinked polymers based on a phosphorus-containing maleimide. Polymers for Advanced Technologies 15 10 (2004) 587-592
63. Kim E., Cho S.Y., Yeu D.M., and Shin S.Y. Low optical loss perfluorinated methacrylates for a single-mode polymer waveguide. Chemistry of Materials 17 5 (2005) 962-966