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]
  Zhiwen HUANG , Qi LIU , Jianping LANG . W/Cu/S cluster-based supramolecular macrocycles and their third-order nonlinear optical responses. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 79-87. doi: 10.11862/CJIC.20240184
2. [2]
  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
3. [3]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
4. [4]
  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
5. [5]
  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
6. [6]
  Jiahui CHEN , Tingting ZHENG , Xiuyun ZHANG , Wei LÜ . Research progress of near-infrared absorption inorganic nanomaterials in photothermal and photodynamic therapy of tumors. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2396-2414. doi: 10.11862/CJIC.20240106
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  Runhua Chen , Qiong Wu , Jingchen Luo , Xiaolong Zu , Shan Zhu , Yongfu Sun . 缺陷态二维超薄材料用于光/电催化CO₂还原的基础与展望. Acta Physico-Chimica Sinica, 2025, 41(3): 2308052-. doi: 10.3866/PKU.WHXB202308052
11. [11]
  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
12. [12]
  Qiaoqiao BAI , Anqi ZHOU , Xiaowei LI , Tang LIU , Song LIU . Construction of pressure-temperature dual-functional flexible sensors and applications in biomedicine. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2259-2274. doi: 10.11862/CJIC.20240128
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
17. [17]
  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
18. [18]
  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
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(510)
Abstract views(504)
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