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Synthesis of novel T-type nonlinear optical polyester with enhanced thermal stability of second harmonic generation for electro-optic applications

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Abstract

2,5-Di-(2′-hydroxyethoxy)benzylidenemalononitrile (3) was prepared and condensed with terephthaloyl chloride to yield novel T-type polyester (4) containing 2,5-dioxybenzylidenemalononitrile groups as NLO-chromophores, which are parts of the polymer backbones. The resulting polymer 4 was soluble in common organic solvents such as acetone and DMF and showed thermal stability up to 280 °C with T g of 83 °C. The second harmonic generation (SHG) coefficient (d 33) of poled polymer film at the 1,064 nm fundamental wavelength was around 4.46 × 10−9 esu. The dipole alignment exhibited high thermal stability even at 10 °C higher than T g, and there was no SHG decay below 95 °C due to the partial main-chain character of polymer structure, which was acceptable for NLO device applications.

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References

  1. Morisaki Y, Chen H, Chujo Y (2003) Synthesis and properties of novel poly(p, phenylenevinylene)s containing a tricarbonyl(arene)chromium unit in the main chain. Polym Bull 50:39–46

    Article  CAS  Google Scholar 

  2. Navarro RE, Armenta-Villegas L, Perez-Martinez AL, Beristain MF, Ogawa T (2007) Synthesis and characterization of poly(dipropargyloxynaphtoates) containing polar Azo dyes. Polym Bull 58:757–765

    Article  CAS  Google Scholar 

  3. Tsutumi N, Yoshizaki S, Sakai W, Kiyotsukuri T (1995) Nonlinear optical polymers. 1. Novel network polyurethane with azobenzene dye in the main frame. Macromolecules 28:6437–6442

    Article  Google Scholar 

  4. Kato M, Kanda K, Kimura T, Matsuda H, Nakanishi H (1996) Synthesis of polymers bearing azo-dye chromophore with photocrosslinkable moiety for nonlinear optics. Polym Bull 36:407–414

    Article  CAS  Google Scholar 

  5. Han KS, Park SK, Shim SY, Jahng WS, Kim NJ (1998) Self-crosslinkable side-chain copolymer for nonlinear optical application. Bull Korean Chem Soc 19:1165–1168

    CAS  Google Scholar 

  6. Umeyama T, Naka K, Bravo MD, Nakanishi A, Chujo Y (2004) Synthesis and properties of cross-linked poly(vinylene-arsine). Polym Bull 52:191–199

    Article  CAS  Google Scholar 

  7. Yu D, Gharavi A, Yu L (1996) Highly stable copolyimides for second-order nonlinear optics. Macromolecules 29:6139–6142

    Article  CAS  Google Scholar 

  8. Tsutsumi N, Morishima M, Sakai W (1998) Nonlinear optical (NLO) polymers. 3. NLO polyimide with dipole moments aligned transverse to the imide linkage. Macromolecules 31:7764–7769

    Article  CAS  Google Scholar 

  9. Lee HJ, Lee MH, Oh MC, Han SG (1999) Synthesis and properties of nonlinear optical polymers based on poly(ether imides) for electrooptical devices. Polym Bull 42:403–409

    Article  CAS  Google Scholar 

  10. Lin B, Xu X (2007) Preparation and properties of cyano-containing polyimide films based on 2,6-bis(4-aminophenoxy)-benzonitrile. Polym Bull 59:243–250

    Article  CAS  Google Scholar 

  11. Lee JH, Lee KS (2000) A hyperbranched nonlinear optical polyester with polar chromophores. Bull Korean Chem Soc 21:847–848

    CAS  Google Scholar 

  12. Lee SH, Kim YK, Won YH (1999) Nonlinear optical properties of poly-p-(phenylene terephthalates) with side group chromophores. Macromolecules 32:342–347

    Article  CAS  Google Scholar 

  13. Lee JY, Jung WT, Lee WJ (2006) Molecular design, synthesis and electro-optic properties of novel Y-type polyesters with high thermal stability of second harmonic generation. Polym Int 55:248–256

    Article  CAS  Google Scholar 

  14. Kim JH, Lee JY, Won DS, Rhee BK (2007) Synthesis and nonlinear optical properties of novel Y-type polyesters with enhanced thermal stability of second harmonic generation. Macromol Res 15:506–512

    CAS  Google Scholar 

  15. Kim JY, Won DS, Lee JY (2008) Preparation and nonlinear optical properties of novel polyesters with enhanced thermal stability of second harmonic generation. Bull Korean Chem Soc 29:181–186

    Article  CAS  Google Scholar 

  16. Kim JY, Lee GY, Lee JY (2008) Preparation and nonlinear optical properties of novel Y-type polyesters with highly enhanced thermal stability of second harmonic generation. Eur Polym J 44:1814–1821

    Article  CAS  Google Scholar 

  17. Won DS, Lee GY, Lee JY (2008) Preparation of a novel Y-type nonlinear optical polyester with high, second harmonic generation thermal stability. Dyes Pigments 78:225–230

    CAS  Google Scholar 

  18. Cisneros JI (1998) Optical characterization of dielectric and semiconductor thin film by use of transmission data. Appl Opt 37:5262–5270

    Article  CAS  Google Scholar 

  19. Herman WN, Hayden LM (1995) Maker fringes revisited: second-harmonic generation from birefringent or absorbing materials. J Opt Soc Am B 12:416–427

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by the 2008 Inje University research grant.

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Authors and Affiliations

  1. Department of Chemistry, Institute of Basic Science, Inje University, 607 Obang-dong, Gimhae, 621-749, South Korea

    Dong-Seon Won, Won-Taek Jung & Ju-Yeon Lee

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  1. Dong-Seon Won
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  2. Won-Taek Jung
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  3. Ju-Yeon Lee
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Correspondence to Ju-Yeon Lee.

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Won, DS., Jung, WT. & Lee, JY. Synthesis of novel T-type nonlinear optical polyester with enhanced thermal stability of second harmonic generation for electro-optic applications. Polym. Bull. 62, 433–443 (2009). https://doi.org/10.1007/s00289-008-0036-5

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  • DOI: https://doi.org/10.1007/s00289-008-0036-5

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