Citation: Chen Lu, Bo Shuhui, He Yanling, Chen Zhuo, Liu Xinhou, Zhen Zhen. Organic Second-Order Nonlinear Optical Chromophores Modified by Isolation Groups[J]. Chinese Journal of Organic Chemistry, ;2017, 37(9): 2263-2274. doi: 10.6023/cjoc201703008 shu

Organic Second-Order Nonlinear Optical Chromophores Modified by Isolation Groups

Chen Lu ^a,b ,
Bo Shuhui ^a,, ,
He Yanling ^a,b ,
Chen Zhuo ^a ,
Liu Xinhou ^a ,
Zhen Zhen ^a,,

a.
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190
b.
University of Chinese Academy of Sciences, Beijing 100043

Corresponding author: Bo Shuhui, boshuhui@mail.ipc.ac.cn Zhen Zhen, zhenzhen@mail.ipc.ac.cn
Received Date: 2 March 2017
Revised Date: 28 April 2017
Available Online: 17 September 2017
Fund Project: the National Natural Science Foundation of China 21504099Project supported by the National Natural Science Foundation of China (No. 21504099)

Figures(18)

Organic second-order nonlinear optical (NLO) chromophores are the main constituent part of nonlinear optical material. Scientists are dedicated to researching on the synthesis of novel chromophores with excellent performance by the facile design and modification of organic second-order NLO chromophores for decades. However, the researches on NLO chromophores in order to achieve the efficient translation of molecular microscopic nonlinearity (hyperpolarizability β) into macroscopic electro-optic (EO) coefficients r₃₃ is still a challenging task. In recent years, a large number of essays report the novel NLO chromophores by adding isolation groups which can change the shape of chromophores and decrease the electrostatic interaction aimed to achieve the bigger EO coefficients. In this review, the recent processes of novel NLO chromophores modified by isolation groups are reviewed systematically and comprehensively.
- organic second-order nonlinear optical materials,
- chromospheres,
- isolation group,
- electro-optic activity,
- dipole-dipole interaction
1. [1]
  Zhang, A.-R.; Xiao, H.-Y.; Cong, S.-Y.; Zhang, M.-L.; Zhang, H.; Bo, S.-H.; Wang, Q.; Zhen, Z.; Liu, X.-H. J. Mater. Chem. C 2015, 3, 370. doi: 10.1039/C4TC01896F
2. [2]
  Chen, D.-T.; Fetterman, H. R.; Chen, A.-T.; Steier, W. H.; Dalton, L. R.; Wang, W.-S.; Shi, Y.-Q. Appl. Phys. Lett. 1997, 70, 3335. doi: 10.1063/1.119162
3. [3]
  Ding, R.; Baehr-Jones, T.; Kim, W.-J.; Spott, A.; Fournier, M.; Fedeli, J.-M.; Huang, S.; Luo, J.-D.; Jen, A. K.-Y.; Dalton, L.; Hochberg, M. J. Lightwave Technol. 2011, 29, 1112. doi: 10.1109/JLT.2011.2122244
4. [4]
  Liang, P.-X.; Mi, Y.-S.; Duan, J.-S.; Yang, Z.; Wang, D.; Cao, H.; He, W.-L. Chin. J. Chem. 2016, 34, 381. doi: 10.1002/cjoc.201500144
5. [5]
6. [6]
  Li, Q.-Q.; Qin, J.-G.; Li, Z. Polym. Bull. 2010, 3(in Chinese).
7. [7]
  Chou, M.-J.; Choi, D.-H.; Sullivan, P. A.; Akelaitis, A. J. P.; Dalton, L. R. Prog. Polym. Sci. 2008, 33, 1013. doi: 10.1016/j.progpolymsci.2008.07.007
8. [8]
  (a) Bai, Y.-W.; Song, N.-H.; Gao, J.-P.; Sun, X.; Wang, X.-M.; Yu, G.-M.; Wang, Z.-Y. J. Am. Chem. Soc. 2005, 127, 2060.
  (b) Dalton, L. In Polymers for Photonics Applications I, Ed.:Lee, K.-S., Springer Berlin Heidelberg, Berlin, Heidelberg, 2002, p. 1.
9. [9]
  (a) Shi, Y.-Q.; Zhang, C.; Zhang, H.; Bechtel, J. H.; Dalton, L. R.; Robinson, B. H.; Steier, W. H. Science 2000, 288, 119.
  (b) Sinyukov, A. M.; Leahy, M. R.; Hayden, L. M.; Haller, M.; Luo, J.-D.; Jen, A. K.-Y.; Dalton, L. R. Appl. Phys. Lett. 2004, 85, 5827.
10. [10]
  Pereverzev, Y. V.; Gunnerson, K. N.; Prezhdo, O. V.; Sullivan, P. A.; Liao, Y.; Olbricht, B. C.; Akelaitis, A. J. P.; Jen, A. K. Y.; Dalton, L. R. J. Phys. Chem. C 2008, 112, 4355. doi: 10.1021/jp077194q
11. [11]
  Udupa, A. H.; Erlig, H.; Tsap, B.; Chang, Y.; Chang, D.; Fetterman, H. R.; Zhang, H.; Sang-Shin, L.; Wang, F.; Steier, W. H.; Dalton, L. R. Electron. Lett. 1999, 35, 1702. doi: 10.1049/el:19991181
12. [12]
  Baehr-Jones, T.; Penkov, B.; Huang, J.; Sullivan, P.; Davies, J.; Takayesu, J.; Luo, J.-D.; Kim, T.-D.; Dalton, L.; Jen, A.; Hochberg, M.; Scherer, A. Appl. Phys. Lett. 2008, 92, 163303. doi: 10.1063/1.2909656
13. [13]
  Tian, Y.-Q.; Chen, C.-Y.; Haller, M. A.; Tucker, N. M.; Ka, J.-W.; Luo, J.-D.; Huang, S.; Jen, A. K. Y. Macromolecules 2007, 40, 97. doi: 10.1021/ma061294x
14. [14]
  Baehr-Jones, T.; Hochberg, M.; Wang, G.-X.; Lawson, R.; Liao, Y.; Sullivan, P. A.; Dalton, L.; Jen, A. K. Y.; Scherer, A. Opt. Express 2005, 13, 5216. doi: 10.1364/OPEX.13.005216
15. [15]
  (a) Yang, Y.-H.; Liu, F.-G.; Wang, H.-R.; Bo, S.-H.; Liu, J.-L.; Qiu, L.; Zhen, Z.; Liu, X.-H. J. Mater. Chem. C 2015, 3, 5297.
  (b) Steier, W. H.; Chen,A.-T.; Lee, S.-S.; Garner, S.; Zhang, H.; Chuyanov, V.; Dalton, L. R.; Wang, F.; Ren, A. S.; Zhang, C.; Todorova, G.; Harper, A.; Fetterman, H. R.; Chen, D.; Udupa, A.; Bhattacharya, D.; Tsap, B. Chem. Phys. 1999, 245, 487.
  (c) Mina, A. M.; Baez, H.; Martins, G. S. P.; Alayo, M. I. J. Non-Crst. Solids. 2008, 354, 2565;
16. [16]
  Clays, K.; Persoons, A. Phys. Rev. Lett. 1991, 66, 2980. doi: 10.1103/PhysRevLett.66.2980
17. [17]
  El-Shishtawy, R. M.; Borbone, F.; Al-amshany, Z. M.; Tuzi, A.; Barsella, A.; Asiri, A. M.; Roviello, A. Dyes Pigm. 2013, 96, 45. doi: 10.1016/j.dyepig.2012.08.002
18. [18]
  (a) Zhang, C.; Dalton, L. R.; Oh, M.-C.; Zhang, H.; Steier, W. H. Chem. Mater. 2001, 13, 3043.
  (b) Harper, A. W.; Sun, S.; Dalton, L. R.; Garner, S. M.; Chen, A.; Kalluri, S.; Steier, W. H.; Robinson, B. H. J. Opt. Soc. Am. B:Opt. Phys. 1998, 15, 329.
  (c) Dalton, L. R.; Harper, A. W.; Robinson, B. H. Proc. Natl Acad. Sci. U. S. A. 1997, 94, 4842.
19. [19]
20. [20]
  Zhang, W.; He, C.-Y.; Xiao, X.-W.; Song, W.-N.; Gao, Y.-C.; Chen, Z.-M.; Dong, Y.-L.; Wu, Y.-Q.; Wang, Q. Chin. J. Chem. 2016, 34, 1006. doi: 10.1002/cjoc.v34.10
21. [21]
  (a) Ma, H.; Liu, S.; Luo, J.-D.; Suresh, S.; Liu, L.; Kang, S. H.; Haller, M.; Sassa, T.; Dalton, L. R.; Jen, A. K.-Y. Adv. Funct. Mater. 2002, 12, 565.
  (b) Wang, H.-R.; Liu, F.-G.; Yang, Y.-H.; Xu, H.-J.; Peng, C.-C.; Bo, S.-H.; Zhen, Z.; Liu, X.-H.; Qiu, L. Dyes Pigm. 2015, 112, 42.
22. [22]
  Wu, W.-B.; Fu, Y.-J.; Wang, C.; Xu, Z.; Ye, C.; Qin, J.-G.; Li, Z. Chin. J. Polym. Sci. 2013, 31, 1415. doi: 10.1007/s10118-013-1343-3
23. [23]
  Hu, C.-L.; Liu, F.-G.; Zhang, H.; Huo, F.-Y.; Yang, Y.-H.; Wang, H.-R.; Xiao, H.-Y.; Chen, Z.; Liu, J.-L.; Qiu, L.; Zhen, Z.; Liu, X.-H.; Bo, S.-H. J. Mater. Chem. C 2015, 3, 11595. doi: 10.1039/C5TC02702K
24. [24]
  Sullivan, P. A.; Rommel, H.; Liao, Y.; Olbricht, B. C.; Akelaitis, A. J. P.; Firestone, K. A.; Kang, J.-W.; Luo, J.-D.; Davies, J. A.; Choi, D. H.; Eichinger, B. E.; Reid, P. J.; Chen, A.-T.; Jen, A. K. Y.; Robinson, B. H.; Dalton, L. R. J. Am. Chem. Soc. 2007, 129, 7523. doi: 10.1021/ja068322b
25. [25]
  Peng, C.-C.; Wu, J.-Y.; Liu, J.-L.; Qiu, L.; Liu, X.-H.; Bo, S.-H.; Zhen, Z. Polym. Chem. 2013, 4, 2703. doi: 10.1039/c3py20935k
26. [26]
  Huang, H.-Y.; Deng, G.-W.; Liu, J.-L.; Wu, J.-Y.; Si, P.; Xu, H.-J.; Bo, S.-H.; Qiu, L.; Zhen, Z.; Liu, X.-H. Dyes Pigm. 2013, 99, 753. doi: 10.1016/j.dyepig.2013.06.034
27. [27]
  Xu, H.-J.; Zhang, M.-L.; Zhang, A.-R.; Deng, G.-W.; Si, P.; Huang, H.-Y.; Peng, C.-C.; Fu, M.-K.; Liu, J.-L.; Qiu, L.; Zhen, Z.; Bo, S.-H.; Liu, X.-H. Dyes Pigm. 2014, 102, 142. doi: 10.1016/j.dyepig.2013.10.042
28. [28]
  Sullivan, P. A.; Akelaitis, A. J. P.; Lee, S. K.; McGrew, G.; Lee, S. K.; Choi, D. H.; Dalton, L. R. Chem. Mater. 2006, 18, 344. doi: 10.1021/cm0517420
29. [29]
  (a) Li, Z.-A.; Li, P.-C.; Dong, S.-C.; Zhu, Z.-C.; Li, Q.-Q.; Zeng, Q.; Li, Z.; Ye, C.; Qin, J.-G. Polymer 2007, 48, 3650.
  (b) Li, Q.-Q.; Li, Z.; Zeng, F.-X.; Gong, W.; Li, Z.-A.; Zhu, Z.-C.; Zeng, Q.; Yu, S.-S.; Ye, C.; Qin, J.-G. J. Phys. Chem. B 2007, 111, 508.
30. [30]
  (a) Wu, W.-B; Qin, J.-G.; Li, Z. Polymer 2013, 54, 4351.
  (b) Li, Z.; Dong, S.; Yu, G.; Li, Z.; Liu, Y.; Ye, C.; Qin, J. Polymer 2007, 48, 5520.
  (c) Kityk, I. V.; Alzayed, N.; Reshak, A. H.; Plucinski, K. J.; Berdowski, J.; Fuks-Janczarek, I.; Miedzinski, R.; Tylczynski, Z. Funct. Mater. Lett. 2011, 04, 357.
31. [31]
  Li, Q.-Q.; Qin, J.-G.; Li, Z. Chin. J. Org. Chem. 2011, 31, 1337(in Chinese).
32. [32]
  Hammond, S. R.; Clot, O.; Firestone, K. A.; Bale, D. H.; Lao, D.; Haller, M.; Phelan, G. D.; Carlson, B.; Jen, A. K. Y.; Reid, P. J.; Dalton, L. R. Chem. Mater. 2008, 20, 3425. doi: 10.1021/cm800054y
33. [33]
  Robinson, B. H.; Dalton, L. R.; Harper, A. W.; Ren, A.; Wang, F.; Zhang, C.; Todorova, G.; Lee, M.; Aniszfeld, R.; Garner, S.; Chen, A.; Steier, W. H.; Houbrecht, S.; Persoons, A.; Ledoux, I.; Zyss, J.; Jen, A. K. Y. Chem. Phys. 1999, 245, 35. doi: 10.1016/S0301-0104(99)00079-8
34. [34]
  Yang, Y.-H.; Wang, H.-R.; Liu, F.-G.; Yang, D.; Bo, S.-H.; Qiu, L.; Zhen, Z.; Liu, X.-H. Phys. Chem. Chem. Phys. 2015, 17, 5776. doi: 10.1039/C4CP05829A
35. [35]
  Liu, F.-G.; Zhang, M.-L.; Xiao, H.-Y.; Yang, Y.-H.; Wang, H.-R.; Liu, J.-L.; Bo, S.-H.; Zhen, Z.; Liu, X.-H.; Qiu, L. J. Mater. Chem. C 2015, 3, 9283. doi: 10.1039/C5TC01610J
36. [36]
  Luo, J.-D.; Haller, M.; Ma, H.; Liu, S.; Kim, T.-D.; Tian, Y.-Q.; Chen, B.-Q.; Jang, S.-H.; Dalton, L. R.; Jen, A. K. Y. J. Phys. Chem. B 2004, 108, 8523. doi: 10.1021/jp036714o
37. [37]
  Cheng, Y.-J.; Luo, J.-D.; Hau, S.; Bale, D. H.; Kim, T.-D.; Shi, Z.-W.; Lao, D. B.; Tucker, N. M.; Tian, Y.-Q.; Dalton, L. R.; Reid, P. J.; Jen, A. K. Y. Chem. Mater. 2007, 19, 1154. doi: 10.1021/cm062340a
38. [38]
  Yang, Y.-H.; Bo, S.-H.; Wang, H.-R.; Liu, F.-G.; Liu, J.-L.; Qiu, L.; Zhen, Z.; Liu, X.-H. Dyes Pigm. 2015, 122, 139. doi: 10.1016/j.dyepig.2015.06.012
39. [39]
  Wu, J.-Y.; Bo, S.-H.; Liu, J.-L.; Zhou, T.-T.; Xiao, H.-Y.; Qiu, L.; Zhen, Z.; Liu, X.-H. Chem. Commun. 2012, 48, 9637. doi: 10.1039/c2cc34747d
40. [40]
  (a) Wu, J.-Y.; Xiao, H.-Y.; Qiu, L.; Zhen, Z.; Liu, X.-H.; Bo, S.-H. RSC Adv. 2014, 4, 49737.
  (b) Wu, J.-Y.; Peng, C.-C.; Xiao, H.-Y.; Bo, S.-H.; Qiu, L.; Zhen, Z.; Liu, X.-H. Dyes Pigm. 2014, 104, 15.
  (c) Wu, J.-Y.; Liu, J.-L.; Zhou, T.-T.; Bo, S.-H.; Qiu, L.; Zhen, Z.; Liu, X.-H. RSC Adv. 2012, 2, 1416.
41. [41]
  Kim, T.-D.; Luo, J.-D.; Tian, Y.-Q.; Ka, J.-W.; Tucker, N. M.; Haller, M.; Kang, J.-W.; Jen, A. K. Y. Macromolecules 2006, 39, 6951. doi: 10.1021/ma0608875
42. [42]
  Zhang, H.; Huo, F.-Y.; Liu, F.-G.; Chen, Z.; Liu, J.-L.; Bo, S.-H.; Zhen, Z.; Qiu, L. RSC Adv. 2016, 6, 99743. doi: 10.1039/C6RA21814H
43. [43]
  Deng, G.-W.; Huang, H.-Y.; Peng, C.-C.; Zhang, A.-R.; Zhang, M.-L.; Bo, S.-H.; Liu, X.-H.; Zhen, Z.; Qiu, L. RSC Adv. 2014, 4395.
44. [44]
  Li, Z.-A.; Wu, W.-B.; Hu, P.; Wu, X.-J.; Yu, G.; Liu, Y.-Q.; Ye, C.; Li, Z.; Qin, J.-G. Dyes Pigm. 2009, 81, 264. doi: 10.1016/j.dyepig.2008.10.014
45. [45]
  Li, Z.; Li, Q.-Q.; Qin, J.-G. Polym. Chem. 2011, 2, 2723. doi: 10.1039/c1py00205h
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