Articles

Synthesis of Novel Organic Nonlinear Optical Chromophores and the Enhancement of Electro-optic Activity of the Additional Donors

  • You Yingcai ,
  • Tang Xianzhong ,
  • Tang Xiang ,
  • Jia Kunpeng ,
  • Wang Yang ,
  • Li Yushu ,
  • Zhang Yu
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  • a State Key Laboratory of Electronic Thin Films and Integrated Devices, University of Electronic Science and Technology of China, Chengdu 610054;
    b People’s Liberation Army 63916 Troops, Beijing 100000

Received date: 2012-09-13

  Revised date: 2012-12-12

  Online published: 2012-12-18

Supported by

Project supported by the National Natural Science Foundation of China (No. 60771044).

Abstract

In order to study the impact of different additional donors on molecular thermal decomposition temperature (Td) value of the chromophores as well as the second polarization (μgβ) value. Three novel materials EFC-OH, EFC-OBu and EFC- OBe were synthesized by attaching additional donors to the benzene ring based on the reported 2-[{4-(4-diethylamino)sty- reneyl}-3-cyano-5,5-dimethyl-5H-furan-2-ylidene]malononitrile (DCDHF-2-V). The three chromophores were characterized by 1H NMR, 13C NHR, FT-IR and elemental analysis. The Td value was determined by TGA testing, and the result showed that three molecules had a good thermal performance. EFC-OBe processing a Td of 278.6 ℃ showed the best among these molecules. The hyperpolarizability was measured and calculated by solvatochromism method. EFC-OBe still showed the best μgβ value of 4.7149×10-44 esu. Comparing to the DCDHF-2-V without additional donors on Td value and μgβ value, additional donors had little effect on Td value while achieved an improvement of one order of magnitude in μgβ values, which indicates that the molecules can work in high temperature and performance better in optics.

Cite this article

You Yingcai , Tang Xianzhong , Tang Xiang , Jia Kunpeng , Wang Yang , Li Yushu , Zhang Yu . Synthesis of Novel Organic Nonlinear Optical Chromophores and the Enhancement of Electro-optic Activity of the Additional Donors[J]. Chinese Journal of Organic Chemistry, 2013 , 33(03) : 530 -534 . DOI: 10.6023/cjoc201209020

References

[1] Feng, J.-K. Acta Chim. Sinica 2005, 63, 1245 (in Chinese).
(封继康, 化学学报, 2005, 63, 1245.)

[2] Qi, X.-Y.; Hu, Q.-Y.; Wang, S.-M.; Yang, F.; Yu, P. Acta Chim. Sinica 2012, 70, 363 (in Chinese).
(祁小云, 胡泉源, 王世敏, 杨飞, 喻平, 化学学报, 2012, 70, 363.)

[3] Liu, Y.-T.; Wang, X.; Liu, X.-Y.; Ji, Y.-Q. Acta Chim. Sinica 2012, 70, 1131 (in Chinese).
(刘英涛, 王鑫, 刘翔宇, 冀永强, 化学学报, 2012, 70, 1131.)

[4] Tang, X. M.S. Thesis, University of Electronic Science and Technology of China, Chengdu, 2010 (in Chinese).
(唐翔, 硕士论文, 电子科技大学, 成都, 2010.)

[5] Li, Q.-Q.; Qin, J.-G.; Li, Z. Chin. J. Org. Chem. 2011, 31, 1337 (in Chinese).
(李倩倩, 秦金贵, 李振 有机化学, 2011, 31, 1337.)

[6] Tang, X.; Tang, X.-Z.; You, Y.-C.; Ren, L.-K.; Wang, Y.; Yan, L.-J. Acta Chim. Sinica 2012, 70, 1565 (in Chinese).
(唐翔, 唐先忠, 游英才, 任立轲, 王洋, 严立京, 化学学报, 2012, 70, 1565.)

[7] 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.

[8] Andreu, R.; Cerdán, M. A.; Franco, S.; Garín, J.; Marco, A. B.; Orduna, J.; Palomas, D.; Villacampa, B.; Alicante, R.; Allain, M. Org. Lett. 2008, 10, 4963.

[9] Guieu, V.; Payrastre, C.; Madaule, Y.; Garcia-Alonso, S.; Lacroix, P. G.; Nakatani, K. Chem. Mater. 2006, 18, 3674.

[10] Marder, S. R. Chem. Commun. 2006, 131.

[11] Luo, S.-S.; Qiu, Y.-Q.; Liu, X.-D.; Liu, C.-G.; Shu, M.-Z. Acta Phys.-Chim. Sinica 2009, 9, 1867 (in Chinese).
(罗姗姗, 仇永清, 刘晓东, 刘春光, 苏忠民, 物理化学学报 2009, 9, 1867.)

[12] Liu, J.-S.; Hou, W.-J.; Feng, S.-W.; Qiu, L; Liu, X.-H.; Zhen, Z. J. Phys. Org. Chem. 2011, 24, 439.

[13] Wang, L.; Liu, J.-L.; Bo, S.-H.; Zhen, Z.; Liu, X.-H. Mater. Lett. 2012, 80, 84.

[14] Li, Q.-Q.; Lu, C.-G.; Fu, E.-Q. J. Phys. Chem. B 2008, 112, 4545.

[15] Piao, X.-Q.; Zhang, X.-M.; Inoue, S.; Yokoyama, S.; Aoki, I.; Miki, H.; Otomo, A.; Tazawa, H. Org. Electron. 2011, 12, 1093.

[16] Piao, X.-Q.; Zhang, X.-M.; Mori, Y.; Koishi, M.; Nakaya, A.; Inoue, S.; Aoki, I.; Otomo, A.; Yokoyama, S. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 47.

[17] Wu, J.-Y.; Liu, J.-L.; Zhou, T.-T.; Bo, S.-H.; Qiu, L.; Zhen, Z.; Liu, X.-H. RSC Adv. 2012, 2, 1416.

[18] Han, L.-K.; Jiang, Y.-D.; Li, W. Mater. Lett. 2008, 62, 1495.

[19] He, M.-Q.; Thomas M. L.; John A. S. Chem. Mater. 2002, 14, 4669.

[20] He, M.-Q.; Thomas M. L.; John A. S. Chem. Mater. 2002, 14, 4662.

[21] Baroja, N. M.; Garin, J.; Orduna, J.; Andreu, R. J. Org. Chem. 2012, 77, 4634.

[22] Tang, X.; Tang, X.-Z.; You, Y.-C. Acta Chim. Sinica 2012, 70, 1565.

[23] Wang, Y.; Tang, X.-Z.; Tang, X. Chem. J. Chin. Univ. 2011, 32, 2327 (in Chinese).
(王洋, 唐先忠, 唐翔, 高等学校化学学报, 2011, 32, 2327.)

[24] Zhan, C.-L.; Wang. D.-Y. Acta Chim. Sinica 2001, 59, 213 (in Chinese).
(詹传郎, 王夺元, 化学学报, 2001, 59, 213.)

[25] Pang, M.-L.; Zhang, P.; Dong, Y.-W.; Wang, Y.-M.; Wang, J.-T.; Meng, J.-B. Acta Chim. Sinica 2011, 69, 11 (in Chinese).
(庞美丽, 张鹏, 董轶望, 王永梅, 王积涛, 孟继本, 化学学报, 2011, 69, 11.)

[26] Sun, Z.-F.; You, X.-Z.; Li, D.-G. Acta Chim. Sinica 1994, 52, 734 (in Chinese).
(孙振范, 游效曾, 李大光, 化学学报, 1994, 52, 734.)

[27] Murugan, N.-A.; Kongste, J. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 16453.

[28] Paduraru, P. M.; Popoff, R. T.; Nair, R. J. Comb. Chem. 2008, 10, 123.
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