Citation: Meng Jin, Zhao-Chen Zhu, Qiu-Yan Liao, Qian-Qian Li, Zhen Li. 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 shu

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

Meng Jin ^a ,
Zhao-Chen Zhu ^a ,
Qiu-Yan Liao ^a ,
Qian-Qian Li ^a,, ,
Zhen Li ^a,b,,

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

Corresponding author: Qian-Qian Li, qianqian-alinda@163.com Zhen Li, lizhen@whu.edu.cn;lichemlab@163.com
Received Date: 4 May 2019
Revised Date: 23 May 2019
Available Online: 24 September 2019

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 d₃₃ 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.
- Second-order nonlinear optics,
- Dendronized polymers,
- Chromophore
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  Li, Z. A.; Wu, W. B.; Ye, C.; Qin, J. G.; Li, Z. New second-order nonlinear optical polymers derived from AB₂ and AB monomers via Sonogashira coupling reaction. Macromol. Chem. Phys. 2010, 211, 916−923. doi: 10.1002/macp.200900605
14. [14]
  Wu, W. B.; Fu, Y. J.; Wang, C.; Ye, C.; Qin, J. G.; Li, Z. A series of hyperbranched polytriazoles containing perfluoroaromatic rings from AB₂-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
15. [15]
  Wu, W. B.; Ye, C.; Yu, G.; Liu, Y. Q.; Qin, J. G.; Li, Z. New hyperbranched polytriazoles containing isolation chromophore moieties derived from AB₄ 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
16. [16]
  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.
17. [17]
  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
18. [18]
  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
19. [19]
  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
20. [20]
  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
21. [21]
  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
22. [22]
  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
23. [23]
  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
24. [24]
  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
25. [25]
  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
26. [26]
  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
27. [27]
  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
28. [28]
  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.
29. [29]
  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
30. [30]
  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
31. [31]
  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
32. [32]
  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
33. [33]
  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
34. [34]
  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 AB₂ monomers via click chemistry under copper(I) catalysis. Macromolecules 2009, 42, 1589−1596. doi: 10.1021/ma8025223
35. [35]
  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.
36. [36]
  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
37. [37]
  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
38. [38]
  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
39. [39]
  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
40. [40]
  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
41. [41]
  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
42. [42]
  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
43. [43]
  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
44. [44]
  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 “a₄ + b₂ + c₂” polymerization and applicaion as explosive chemosensor and PLED. Chinese J. Polym. Sci. 2013, 31, 1432−1442. doi: 10.1007/s10118-013-1328-2
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