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
1. [1]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
2. [2]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
3. [3]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
4. [4]
  Min LI , Xianfeng MENG . Preparation and microwave absorption properties of ZIF-67 derived Co@C/MoS₂ nanocomposites. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1932-1942. doi: 10.11862/CJIC.20240065
5. [5]
  Jiajia Li , Xiangyu Zhang , Zhihan Yuan , Zhengyang Qian , Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073
6. [6]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105
7. [7]
  Jiaxin Su , Jiaqi Zhang , Shuming Chai , Yankun Wang , Sibo Wang , Yuanxing Fang . Optimizing Poly(heptazine imide) Photoanodes Using Binary Molten Salt Synthesis for Water Oxidation Reaction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408012-. doi: 10.3866/PKU.WHXB202408012
8. [8]
  Xin Lv , Hongxing Zhang , Kaibo Duan , Wenhui Dai , Zhihui Wen , Wei Guo , Junsheng Hao . Lighting the Way Against Cancer: Photodynamic Therapy. University Chemistry, 2024, 39(5): 70-79. doi: 10.3866/PKU.DXHX202309090
9. [9]
  Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
10. [10]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
11. [11]
  Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO₂ methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
12. [12]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046
13. [13]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
14. [14]
  Zizheng LU , Wanyi SU , Qin SHI , Honghui PAN , Chuanqi ZHAO , Chengfeng HUANG , Jinguo PENG . Surface state behavior of W doped BiVO₄ photoanode for ciprofloxacin degradation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 591-600. doi: 10.11862/CJIC.20230225
15. [15]
  Ruoxi Sun , Yiqian Xu , Shaoru Rong , Chunmiao Han , Hui Xu . The Enchanting Collision of Light and Time Magic: Exploring the Footprints of Long Afterglow Lifetime. University Chemistry, 2024, 39(5): 90-97. doi: 10.3866/PKU.DXHX202310001
16. [16]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
17. [17]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
18. [18]
  Yuhang Jiang , Weijie Liu , Jiaqi Cai , Jiayue Chen , Yanping Ren , Pingping Wu , Liulin Yang . A Journey into the Science and Art of Sugar: “Dispersion of Light and Optical Rotation of Matter” Science Popularization Experiment. University Chemistry, 2024, 39(9): 288-294. doi: 10.12461/PKU.DXHX202401054
19. [19]
  Xiaxue Chen , Yuxuan Yang , Ruolin Yang , Yizhu Wang , Hongyun Liu . Adjustable Polychromatic Fluorescence: Investigating the Photoluminescent Properties of Copper Nanoclusters. University Chemistry, 2024, 39(9): 328-337. doi: 10.3866/PKU.DXHX202308019
20. [20]
  Mengyao Shi , Kangle Su , Qingming Lu , Bin Zhang , Xiaowen Xu . Determination of Potassium Content in Tobacco Stem Ash by Flame Atomic Absorption Spectroscopy. University Chemistry, 2024, 39(10): 255-260. doi: 10.12461/PKU.DXHX202404105

Get Citation

PDF

XML

Metrics

PDF Downloads(510)
Abstract views(476)
HTML views(4)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142