Dendronized Polymers with High FTC-chromophore Loading Density: Large Second-order Nonlinear Optical Effects, Good Temporal and Thermal Stability

Meng Jin; Zhao-Chen Zhu; Qiu-Yan Liao; Qian-Qian Li; Zhen Li

doi:10.1007/s10118-019-2307-z

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Dendronized Polymers with High FTC-chromophore Loading Density: Large Second-order Nonlinear Optical Effects, Good Temporal and Thermal Stability

ARTICLE | Updated：2019-09-24

- Dendronized Polymers with High FTC-chromophore Loading Density: Large Second-order Nonlinear Optical Effects, Good Temporal and Thermal Stability
- Chinese Journal of Polymer Science Vol. 38, Issue 2, Pages: 118-125(2020)
- Affiliations：
  
  a.Department of Chemistry, Sauvage Center for Molecular Sciences, Wuhan University, Wuhan 430072, China
  b.Institute of Molecular Aggregation Science, Tianjin University, Tianjin 300072, China
- Author bio：
  
  qianqian-alinda@163.com (Q.Q.L.)
  lizhen@whu.edu.cn,lichemlab@163.com (Z.L.)
- Funds：
- DOI：10.1007/s10118-019-2307-z
  CLC：
- Received：04 May 2019，
  
  Revised：2019-5-23，
  
  Accepted：25 May 2019，
  
  Online First：24 September 2019，
  
  Published：2020-02
- Accepted：
Scan QR Code
Jin, M.; Zhu, Z. C.; Liao, Q. Y.; Li, Q. Q.; Li, Z. Dendronized polymers with high FTC-chromophore loading density: large second-order nonlinear optical effects, good temporal and thermal stability. Chinese J. Polym. Sci. 2020, 38, 118–125.

Meng Jin, Zhao-Chen Zhu, Qiu-Yan Liao, et al. Dendronized Polymers with High FTC-chromophore Loading Density: Large Second-order Nonlinear Optical Effects, Good Temporal and Thermal Stability[J]. Chinese Journal of Polymer Science, 2020, 38(2): 118-125.
Jin, M.; Zhu, Z. C.; Liao, Q. Y.; Li, Q. Q.; Li, Z. Dendronized polymers with high FTC-chromophore loading density: large second-order nonlinear optical effects, good temporal and thermal stability. Chinese J. Polym. Sci. 2020, 38, 118–125. DOI： 10.1007/s10118-019-2307-z.

Meng Jin, Zhao-Chen Zhu, Qiu-Yan Liao, et al. Dendronized Polymers with High FTC-chromophore Loading Density: Large Second-order Nonlinear Optical Effects, Good Temporal and Thermal Stability[J]. Chinese Journal of Polymer Science, 2020, 38(2): 118-125. DOI： 10.1007/s10118-019-2307-z.

摘要

Abstract

In this study

two new dendronized nonlinear optical (NLO) polymers were synthesized with high FTC chromophore loading density by introduction of high generation chromophore dendrons on the side chains. Due to their suitable molecular weights

both of them possessed good solubility in common solvents. They also inherited the advantages of dendrimers (large NLO coefficient)

especially for

PG2

whose NLO coefficient

value was as high as 282 pm·V

–1

. Also

PG2

had a good temporal stability with 80% of its maximum value being retained at the temperature as high as 129 °C.

关键词

Keywords

references

Dalton, L. R.; Sullivan, P. A.; Bale, D. H . Electric field poled organic electro-optic materials: state of the art and future prospects . Chem. Rev. , 2010 . 110 25 - 55 . DOI: 10.1021/cr9000429 http://doi.org/10.1021/cr9000429 .

Bai, Y.; Song, N. H.; Gao, J. P.; Sun, X.; Wang, X. M.; Yu, G. M.; Wang, Z. Y . A new approach to highly electrooptically active materials using cross-linkable, hyperbranched chromophore-containing oligomers as a macromolecular dopant . J. Am. Chem. Soc. , 2005 . 127 2060 - 2061 . DOI: 10.1021/ja042854f http://doi.org/10.1021/ja042854f .

Luo, J. D.; Huang, S.; Shi, Z. W.; Polishak, B. M.; Zhou, X. H.; Jen, A. K. Y . Tailored organic electro-optic materials and their hybrid systems for device applications . Chem. Mater. , 2011 . 23 544 - 553 . DOI: 10.1021/cm1022344 http://doi.org/10.1021/cm1022344 .

Yu, D.; Gharavi, A.; Yu, L. P . Novel aromatic polyimides for nonlinear optics . J. Am. Chem. Soc. , 1995 . 117 11680 - 11686 . DOI: 10.1021/ja00152a008 http://doi.org/10.1021/ja00152a008 .

Wu, W. B.; Tang, R.; Li, Q. Q.; Li, Z . Functional hyperbranched polymers with advanced optical, electrical and magnetic properties . Chem. Soc. Rev. , 2015 . 44 3997 - 4022 . DOI: 10.1039/C4CS00224E http://doi.org/10.1039/C4CS00224E .

Bhattacharjee, Y. L, S.; Dalton, L. R . Antiparallel-aligned neutral ground state and zwitterionic chromophores as a nonlinear optical material . J. Am. Chem. Soc. , 2006 . 128 6847 - 6853 . DOI: 10.1021/ja057903i http://doi.org/10.1021/ja057903i .

Huang, W.; Jin, Z. A.; Shi, Z. W.; Intemann, J. J.; Li, M.; Luo, J. D.; Jen, A. K. Y . Spontaneous thermal crosslinking of a sydnone containing side-chain polymer with maleimides through a convergent [3 + 2] dual cycloaddition cycloreversion process for electro-optics . Polym. Chem. , 2013 . 4 5760 - 5767 . DOI: 10.1039/c3py00694h http://doi.org/10.1039/c3py00694h .

Dini, D.; Calvete, M. J. F.; Hanack, M . Nonlinear optical materials for the smart filtering of optical radiation . Chem. Rev. , 2016 . 116 2103 - 2140 . DOI: 10.1021/acs.chemrev.5b00515 http://doi.org/10.1021/acs.chemrev.5b00515 .

Benabid, F.; Knight, J. C.; Antonopoulos, G.; Russell, P. S. J . Stimulated raman scattering in hydrogen-filled hollow-core photonic crystal fiber . Science , 2002 . 298 399 - 402 . DOI: 10.1126/science.1076408 http://doi.org/10.1126/science.1076408 .

Marks, T. J.; Ratner, M. A . Design, synthesis, and properties of molecule-based assemblies with large second-order optical nonlinearities . Angew. Chem. Int. Ed. , 1995 . 34 155 - 173 . DOI: 10.1002/(ISSN)1521-3773 http://doi.org/10.1002/(ISSN)1521-3773 .

Luo, J. D.; Zhou, X. H.; Jen, A. K. Y . Rational molecular design and supramolecular assembly of highly efficient organic electro-optic materials . J. Mater. Chem. , 2009 . 19 7410 - 7424 . DOI: 10.1039/b907173c http://doi.org/10.1039/b907173c .

Li, Z. A.; Wu, W. B.; Ye, C.; Qin, J. G.; Li, Z . New main-chain hyperbranched polymers: facile synthesis, structural control, and second-order nonlinear optical properties . Polymer , 2012 . 53 153 - 160 . DOI: 10.1016/j.polymer.2011.11.015 http://doi.org/10.1016/j.polymer.2011.11.015 .

Li, Z. A.; Wu, W. B.; Ye, C.; Qin, J. G.; Li, Z . New second-order nonlinear optical polymers derived from AB 2 and AB monomers via Sonogashira coupling reaction . Macromol. Chem. Phys. , 2010 . 211 916 - 923 . DOI: 10.1002/macp.200900605 http://doi.org/10.1002/macp.200900605 .

Wu, W. B.; Fu, Y. J.; Wang, C.; Ye, C.; Qin, J. G.; Li, Z . A series of hyperbranched polytriazoles containing perfluoroaromatic rings from AB 2 -type monomers: Convenient syntheses by click chemistry under copper(I) catalysis and enhanced optical nonlinearity . Chem. Asian J. , 2011 . 6 2787 - 2795 . DOI: 10.1002/asia.v6.10 http://doi.org/10.1002/asia.v6.10 .

Wu, W. B.; Ye, C.; Yu, G.; Liu, Y. Q.; Qin, J. G.; Li, Z . New hyperbranched polytriazoles containing isolation chromophore moieties derived from AB 4 monomers through click chemistry under copper(I) catalysis: Improved optical transparency and enhanced NLO effects . Chem. Eur. J. , 2012 . 18 4426 - 4434 . DOI: 10.1002/chem.v18.14 http://doi.org/10.1002/chem.v18.14 .

Li, Z. A.; Wu, W. B.; Ye, C.; Qin, J. G; Li, Z . New hyperbranched polyaryleneethynylene containing azobenzene chromophore moieties in the main chain: facile synthesis, large optical nonlinearity and high thermal stability . Polym. Chem. , 2010 . 1 78 - 81 . .

Li, Z. A; Yu, G.; Liu, Y. Q.; Ye, C.; Qin, J. G.; Li, Z . Dendronized polyfluorenes with high azo-chromophore loading density: convenient synthesis and enhanced second-order nonlinear optical effects . Macromolecules , 2009 . 42 6463 - 6472 . DOI: 10.1021/ma901108r http://doi.org/10.1021/ma901108r .

Chen, P. Y.; Yin, X. Y.; Xie, Y. J.; Li, S. F.; Luo, S. Y.; Zeng, H. Y.; Guo, G. C.; Li, Q. Q.; Li, Z . FTC-containing molecules: large second-order nonlinear optical performance and excellent thermal stability, and the key development of the ‘‘Isolation Chromophore’’ concept . J. Mater. Chem. C , 2016 . 4 11474 - 11481 . DOI: 10.1039/C6TC04282A http://doi.org/10.1039/C6TC04282A .

Holman, J.; Ye, S.; Neivandt, D. J.; Davies, P. B . Studying nanoparticle-induced structural changes within fatty acid multilayer films using sum frequency generation vibrational spectroscopy . J. Am. Chem. Soc. , 2004 . 126 14322 - 14323 . DOI: 10.1021/ja046954x http://doi.org/10.1021/ja046954x .

Shi, Z. W.; Luo, J. D.; Jen, A. K. Y . Achieving excellent electro-optic activity and thermal stability in poled polymers through an expeditious crosslinking process . J. Mater. Chem. , 2012 . 22 951 - 959 . DOI: 10.1039/C1JM14254B http://doi.org/10.1039/C1JM14254B .

Tang, R. L.; Chen, H.; Zhou, S. M.; Xiang, W.; Tang, X.; Liu, B.; Dong, Y.; Zeng, H.; Li, Z . New ‘‘X-type’’ second-order nonlinear optical (NLO) dendrimers: fewer chromophore moieties and high NLO effects . Polym. Chem. , 2015 . 6 5580 - 5589 . DOI: 10.1039/C5PY00155B http://doi.org/10.1039/C5PY00155B .

Kolli, B.; Pandey, S.; Mishra, S. P.; Kanai, T.; Joshi, M. P.; Mohan, R. S.; Samu, A. B . Synthesis and characterization of azo-bisbenzylidene-based polymers for second order nonlinear optics . Polym. Chem. , 2013 . 51 4317 - 4324 . DOI: 10.1002/pola.26842 http://doi.org/10.1002/pola.26842 .

Wu, W. B.; Fu, Y. J.; Wang, C.; Xu, Z.; Ye, C.; Qin, J. G.; Li, Z . Second-order nonlinear optical hyperbranched polymer containing isolation chromophore moieties derived from both “H”-type and star-type chromophores . Chinese J. Polym. Sci. , 2013 . 31 1415 - 1423 . DOI: 10.1007/s10118-013-1343-3 http://doi.org/10.1007/s10118-013-1343-3 .

Li, Z. A.; Li, Z.; Di, C. A.; Zhu, Z. C.; Li, Q. Q.; Zeng, Q.; Zhang, K.; Liu, Y. Q.; Ye, C.; Qin, J. G . Structural control of the side-chain chromophores to achieve highly efficient nonlinear optical polyurethanes . Macromolecules , 2006 . 39 6951 - 6961 . DOI: 10.1021/ma0608875 http://doi.org/10.1021/ma0608875 .

Li, Z. A.; Li, P. C.; Dong, S. C.; Zhu, Z. C.; Li, Q. Q.; Zeng, Q.; Li, Z.; Ye, C.; Qin, J. G . Controlling nonlinear optical effects of polyurethanes by adjusting isolation spacers through facile postfunctional polymer reactions . Polymer , 2007 . 48 3650 - 3657 . DOI: 10.1016/j.polymer.2007.04.062 http://doi.org/10.1016/j.polymer.2007.04.062 .

Zeng, Q.; Li, Z. A.; Li, Z.; Ye, C.; Qin, J. G.; Tang, B. Z . Convenient attachment of highly polar azo chromophore moieties to disubstituted polyacetylene through polymer reactions by using “click” chemistry . Macromolecules , 2007 . 40 5634 - 5637 . DOI: 10.1021/ma070846o http://doi.org/10.1021/ma070846o .

Chen, P. Y.; Liu, G. C.; Zhang, H. Y.; Jin, M.; Han, M. M.; Cheng, Z. Y.; Peng, Q.; Li, Q. Q.; Li, Z . A rigid ringlike molecule: large second-order nonlinear optical performance, good temporal and thermal stability, and ideal spherical structure conforming to the ‘‘site isolation’’ principle . J. Mater. Chem. C , 2018 . 6 6784 - 6791 . DOI: 10.1039/C8TC01598H http://doi.org/10.1039/C8TC01598H .

Chen, P. Y.; Li, Z . The design of second-order nonlinear optical dendrimers: from “branch only” to “root containing” . Chinese J. Polym. Sci. , 2017 . 7 793 - 798 . .

Chen, P. Y.; Zhang, H. Y.; Han, M. M.; Cheng, Z. Y.; Peng, Q.; Li, Q. Q.; Li, Z . Janus molecules: large second-order nonlinear optical performance, good temporal stability, excellent thermal stability and spherical structure with optimized dendrimer structure . Mater. Chem. Front. , 2018 . 2 1374 - 1382 . DOI: 10.1039/C8QM00128F http://doi.org/10.1039/C8QM00128F .

Wu, W. B.; Huang, Q.; Qiu, G. F.; Ye, C.; Qin, J. G.; Li, Z . Aromatic/perfluoroaromatic self-assembly effect: an effective strategy to improve the NLO effect . J. Mater. Chem. , 2012 . 22 18486 - 18495 . DOI: 10.1039/c2jm33129b http://doi.org/10.1039/c2jm33129b .

Ma, H.; Liu, S.; Luo, J.; Suresh, S.; Liu, L.; Kang, S. H.; Haller, M.; Sassa, T.; Dalton, L. R.; Jen, A. K. Y . Highly efficient and thermally stable electro-optical dendrimers for photonics . Adv. Funct. Mater. , 2002 . 12 565 - 574 . DOI: 10.1002/1616-3028(20020916)12:9<565::AID-ADFM565>3.0.CO;2-8 http://doi.org/10.1002/1616-3028(20020916)12:9<565::AID-ADFM565>3.0.CO;2-8 .

Wu, W. B.; Huang, L. J.; Song, C. F.; Yu, G.; Ye, C.; Liu, Y. Q.; Qin, J. G.; Li, Q. Q.; Li, Z . Novel global-like second-order nonlinear optical dendrimers: convenient synthesis through powerful click chemistry and large NLO effects achieved by using simple azo chromophore . Chem. Sci. , 2012 . 3 1256 - 1261 . DOI: 10.1039/c2sc00834c http://doi.org/10.1039/c2sc00834c .

Zhu, Z. C.; Li, Z. A.; Tan, Y.; Li, Z.; Li, Q. Q.; Zeng, Q.; Ye, C.; Qin, J. G . New hyperbranched polymers containing second-order nonlinear optical chromophores: synthesis and nonlinear optical characterization . Polymer , 2006 . 47 7881 - 7888 . DOI: 10.1016/j.polymer.2006.09.047 http://doi.org/10.1016/j.polymer.2006.09.047 .

Li, Z. A.; Yu, G.; Hu, P.; Ye, C.; Liu, Y. Q.; Qin, J. G.; Li, Z . New azo chromophore containing hyperbranched polytriazoles derived from AB 2 monomers via click chemistry under copper(I) catalysis . Macromolecules , 2009 . 42 1589 - 1596 . DOI: 10.1021/ma8025223 http://doi.org/10.1021/ma8025223 .

Ronchi, M.; Pizzotti, M.; Biroli, A. O.; Righetto, S.; Ugo, R . Second-order nonlinear optical (NLO) properties of a multichromophoric system based on an ensemble of four organic NLO chromophores nanoorganized on a cyclotetrasiloxane architecture . J. Phys. Chem. C , 2009 . 113 2745 - 2760 . .

Yang, H. T.; Tang, R. L.; Wu, W. B.; Liu, W.; Guo, Q.; Liu, Y. L.; Xu, S. G.; Cao, S. K.; Li, Z . A series of dendronized hyperbranched polymers with dendritic chromophore moieties in the periphery: convenient synthesis and large nonlinear optical effects . Polym. Chem. , 2016 . 7 4016 - 4024 . DOI: 10.1039/C6PY00546B http://doi.org/10.1039/C6PY00546B .

Li, Z. A.; Wu, W. B.; Li, Q. Q.; Yu, G.; Xiao, L.; Liu, Y. Q.; Ye, C.; Qin, J. G.; Li, Z . High-generation second-order nonlinear optical (NLO) dendrimers: convenient synthesis by click chemistry and the increasing trend of NLO effects . Angew. Chem. Int. Ed. , 2010 . 49 2763 - 2767 . DOI: 10.1002/anie.200906946 http://doi.org/10.1002/anie.200906946 .

Liu, J. L.; Wang, L.; Zhen, Z.; Liu, X. H . Synthesis of novel polyarylate with elecrooptical chromophores as side chain as electro-optic host polymer . Colloid Polym. Sci. , 2012 . 290 1215 - 1220 . DOI: 10.1007/s00396-012-2695-x http://doi.org/10.1007/s00396-012-2695-x .

Liu, W.; Yang, H. T.; Wu, W. B.; Gao, H. Y.; Xu. S. D.; Guo, Q.; Liu, Y. L.; Xu, S. G . Calix [4] resorcinarene-based branched macromolecules for all-optical photorefractive applications . J. Mater. Chem. C , 2016 . 4 10684 - 10690 . DOI: 10.1039/C6TC04062D http://doi.org/10.1039/C6TC04062D .

Hu, C. L.; Chen, Z.; Xiao, H. Y.; Zhen, Z.; Liu, X. H.; Bo, S. H . Synthesis and characterization of a novel indoline based nonlinear optical chromophore with excellent electro-optic activity and high thermal stability by modifying the π -conjugated bridges . J. Mater. Chem. C , 2017 . 5 5111 - 5118 . DOI: 10.1039/C7TC00735C http://doi.org/10.1039/C7TC00735C .

Li, Z.; Qin, J. G.; Li, S. J.; Ye, C.; Luo, J.; Cao, Y . Polyphophazene containing indole-based dual chromophores: synthesis and nonlinear optical characterization . Macromolecules , 2002 . 35 9232 - 9235 . DOI: 10.1021/ma020769r http://doi.org/10.1021/ma020769r .

Li, Z.; Huang, C.; Hua, J. L.; Qin, J. G.; Yang, Z.; Ye, C . A new post-functional approach to prepare second-order nonlinear optical polyphophazenes containing sulfonyl-based chromophore . Macromolecules , 2004 . 37 371 - 376 . DOI: 10.1021/ma035044h http://doi.org/10.1021/ma035044h .

Wu, W. B.; Li, Z . Further improvement of the macroscopic NLO coefficient and optical transparency of hyperbranched polymers by enhancing the degree of branching . Polym. Chem. , 2014 . 5 5100 - 5108 . DOI: 10.1039/C4PY00419A http://doi.org/10.1039/C4PY00419A .

Wu, W. B.; Ye, S. H.; Huang, L. J.; Yu, G.; Liu, Y. Q.; Qin, J. G.; Li, Z . A functional conjugated hyperbranched polymer derived from tetraphenylethene and oxadiazole moieties: synthesis by one-pot “a 4 + b 2 + c 2 ” polymerization and applicaion as explosive chemosensor and PLED . Chinese J. Polym. Sci. , 2013 . 31 1432 - 1442 . DOI: 10.1007/s10118-013-1328-2 http://doi.org/10.1007/s10118-013-1328-2 .

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