Citation: WANG Liu-Heng, PENG Rong-Zong, ZHAO Yu-Xia, WU Fei-Peng. Synthesis and Optical Limiting Behaviors of Malononitrile Derivatives[J]. Acta Physico-Chimica Sinica, ;2014, 30(5): 980-986. doi: 10.3866/PKU.WHXB201403031 shu

Synthesis and Optical Limiting Behaviors of Malononitrile Derivatives

1.
1 Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China;
2 University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Received Date: 22 January 2014
Available Online: 3 March 2014
Fund Project:

A series of malononitrile derivatives (D1-D7) with different electron donors and conjugation lengths were designed and synthesized. Their structures were characterized using ¹H and ¹³C nuclear magnetic resonance (NMR) spectroscopies, and high-resolution mass spectrometry (HRMS). Their linear photophysical properties were investigated in dimethylformamide (DMF) solutions, their optical stabilities were investigated using photobleaching experiments, and their thermal stabilities were determined using thermogravimetric analysis (TGA). The optical limiting behaviors of D1-D7 under an 800 nm femtosecond pulsed laser (Ti:sapphire laser, ~130 fs, 1000 Hz) were investigated. The results showed that four of the compounds (D4-D7), which had dialkylamines as electron donors, exhibited significant optical limiting behaviors, based on two-photon absorption (2PA), but the other three compounds (D1-D3), which had either weak donors or short conjugation lengths, showed very weak optical limiting behaviors. All the compounds had od photochemical and thermal stabilities. The 2PA cross-sections and optothermal stabilities of this series of compounds increased with increasing conjugation length or electron-donating ability of the alkylamine groups in their structures. D7, which had the best properties, is a potential candidate for optical limiting applications under an 800 nm femtosecond pulsed laser.
- Optical limiting,
- 800 nm ultrafast laser,
- Two-photon absorption,
- Nonlinear transmission,
- Malononitrile derivative
1. [1]
  
  (1) Tutt, L.W.; Boggess, T. F. Prog. Quantum Electron. 1993, 17, 299. doi: 10.1016/0079-6727(93)90004-S
2. [2]
  (2) Zheng, L. S.; Feng, M.; Zhan, H. B. Acta Phys. -Chim. Sin. 2012, 28, 208. [郑立思, 冯苗, 詹红兵. 物理化学学报, 2012, 28, 208.] doi: 10.3866/PKU.WHXB201228208
3. [3]
  (3) He, G. S.; Gvishi, R.; Prasad, P. N.; Reinhardt, B. A. Opt. Commun. 1995, 117, 133. doi: 10.1016/0030-4018(95)00097-R
4. [4]
  (4) He, G. S.; Bhawalkar, J. D.; Zhao, C. F.; Prasad, P. N. Appl. Phys. Lett. 1995, 67, 2433. doi: 10.1063/1.114598
5. [5]
  (5) He, G. S.; Tan, L. S.; Zheng, Q.; Prasad, P. N. Chem. Rev. 2008, 108, 1245. doi: 10.1021/cr050054x
6. [6]
  (6) Ehrlich, J. E.;Wu, X. L.; Lee, I. Y. S.; Hu, Z. Y.; Röckel, H.; Marder, S. R.; Perry, J.W. Opt. Lett. 1997, 22, 1843. doi: 10.1364/OL.22.001843
7. [7]
  (7) Morel, Y.; Irimia, A.; Najechalski, P.; Kervella, Y.; Stephan, O.; Baldeck, P. L.; Andraud, C. J. Chem. Phys. 2001, 114, 5391. doi: 10.1063/1.1351160
8. [8]
  (8) Silly, M. G.; Porre? s, L.; Mongin, O.; Chollet, P. A.; Blanchard-Desce, M. Chem. Phys. Lett. 2003, 379, 74. doi: 10.1016/j.cplett.2003.08.017
9. [9]
  (9) Mongin, O.; Porrés, L.; Katan, C.; Pons, T.; Mertzb, J.; Blanchard-Desce, M. Tetrahedron Lett. 2003, 44, 8121. doi: 10.1016/j.tetlet.2003.09.025
10. [10]
  (10) He, G. H.; Zhang, J. X.; Ye, L. H.; Cui, Y. P.; Li, Z. H.; Lai, J. C.; He, A. Z. Acta Phys. Sin. 2003, 52, 1929. [何国华, 张俊祥, 叶莉华, 崔一平, 李振华, 来建成, 贺安之. 物理学报, 2003, 52, 1929.]
11. [11]
  (11) Charlot, M.; Izard, N.; Mongin, O.; Riehl, D.; Blanchard-Desce, M. Chem. Phys. Lett. 2006, 417, 297. doi: 10.1016/j.cplett.2005.10.033
12. [12]
  (12) Gu, B.; Ji,W.; Patil, P. S.; Dharmaprakash, S. M. J. Appl. Phys. 2008, 103, 103511. doi: 10.1063/1.2924419
13. [13]
  (13) Four, M.; Riehl, D.; Mongin, O.; Blanchard-Desce, M.; Lawson-Daku, L. M.; Moreau, J.; Chauvin, J.; Delairef, J. A.; Lemercier, G. Phys. Chem. Chem. Phys. 2011, 13, 17304. doi: 10.1039/c1cp21661a
14. [14]
  (14) Lin, T. C.; Guo, F. L.; Li, M. H.; Liu, C. Y. Chem. Asian J. 2013, 8, 2102. doi: 10.1002/asia.201300223
15. [15]
  (15) Lin, T. C.; Li, M. H.; Liu, C. Y.; Lin, J. H.; Shen, Y. K.; Lee, Y. H. J. Mater. Chem. C 2013, 1, 2764. doi: 10.1039/c3tc00623a
16. [16]
  (16) He, G. S.;Weder, C.; Smith, P.; Prasad, P. N. IEEE J. Quantum Electron. 1998, 34, 2279.
17. [17]
  (17) He, G. S.; Swiatkiewicz, J.; Jiang, Y.; Prasad, P. N.; Reinhardt, B. A.; Tan, L. S.; Kannan, R. J. Phys. Chem. A 2000, 104, 4805. doi: 10.1021/jp000370+
18. [18]
  (18) Lee, K. S.; Lee, J. H.; Choi, H.; Cha, M.; Chung, M. A.; Kim, Y. J.; Jung, S. D. Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A 2001, 370, 155.
19. [19]
  (19) Zheng, Q.; He, G. S.; Lu, C.; Prasad, P. N. J. Mater. Chem. 2005, 15, 3488. doi: 10.1039/b508005c
20. [20]
  (20) Zheng, Q.; Gupta, S. K.; He, G. S.; Tan, L. S.; Prasad, P. N. Adv. Funct. Mater. 2008, 18, 2770. doi: 10.1002/adfm.v18:18
21. [21]
  (21) Li, C.; Yang, K.; Feng, Y.; Su, X.; Yang, J.; Jin, X.; Shui, M.; Wang, Y.; Zhang, X.; Song, Y.; Xu, H. J. Phys. Chem. B 2009, 113, 15730. doi: 10.1021/jp906057y
22. [22]
  (22) Tang, C.; Zheng, Q.; Zhu, H.;Wang, L.; Chen, S. C.; Ma, E.; Chen, X. J. Mater. Chem. C 2013, 1, 1771. doi: 10.1039/c2tc00780k
23. [23]
  (23) Wu, J.; Shi, M.; Zhao, Y.;Wu, F. Dyes Pigments 2008, 76, 690. doi: 10.1016/j.dyepig.2007.01.007
24. [24]
  (24) Wang, L.; Zhao, Y.; Guan, J.;Wu, F. Appl. Phys. Lett. 2013, 102, 251906. doi: 10.1063/1.4812402
25. [25]
  (25) Wang, G.W.; Cheng, B. Arkivoc 2004, 5, 4.
26. [26]
  (26) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508. doi: 10.1021/jo00128a024
27. [27]
  (27) Park, B. S.; El-deeb, I. M.; Yoo, K. H.; Han, D. K.; Tae, J. S.; Lee, S. H. Bull. Korean Chem. Soc. 2012, 33, 3629. doi: 10.5012/bkcs.2012.33.11.3629
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1.
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