Citation: Chen Lei, Tang Xiang, Jia Kun, Tang Xianzhong. Synthesis and Properties of Organic Nonlinear Optical Chromophores Containing Azo-and Furan-Based Conjugated Bridge[J]. Chinese Journal of Organic Chemistry, ;2016, 36(9): 2197-2203. doi: 10.6023/cjoc201601005 shu

Synthesis and Properties of Organic Nonlinear Optical Chromophores Containing Azo-and Furan-Based Conjugated Bridge

1.
State Key Laboratory of Electronic Thin Films and Integrated Devices, School of Microelectronics and Solid-State Electronics, University of Electronic Science and Technology of China, Chengdu 610054

Corresponding author: Tang Xianzhong, txzhong@uestc.edu.cn
Received Date: 5 January 2016
Revised Date: 23 March 2016

Figures(4)

In this work, novel organic non-linear optical chromophore containing azo-furan based conjugation bridge (EFNFC) was designed and synthesized. Moreover, the optical and thermal properties of EFNFC were systematically compared with those of two different conjugation bridges of vinyl-furan (EFFC) and azo-benzene (EFNC) containing same electron donor and acceptor moieties, respectively. It was found that similar maximum absorption wavelength in DMSO solution was detected for EFNFC (573 nm) and EFNC (568 nm), which indicated an improved visible light transmittance compared to EFFC. Meanwhile, the second-order polarizability of EFNFC (4.479×10^-49 esu) was lower than that of EFNC (5.971×10^-49 esu), but larger than that of EFFC (3.194×10^-49 esu) according to the solvatochromism test. All three chromophores exhibited good thermal stability as their 5% decomposition temperatures (T_d) were over 250℃, especially the highest T_d of 275℃ was detected from the synthesized novel EFNFC chromophore.
- nonlinear optics,
- azo compounds,
- density functional theory,
- solvatochromism method,
- thermal stability
1. [1]
  Liu, F.-G.; Wang, H.-R.; Yang, Y.-H.; Xu, H.-J.; Yang, D.; Bo, S.-H.; Liu, J.-H.; Zhen, Z.; Liu, X.-H.; Qiu, L. Dyes Pigm. 2015, 114, 196. doi: 10.1016/j.dyepig.2014.11.015
2. [2]
  Morales, A.-R.; Frazer, A.; Woodward, A.-W.; Ahn-White, H.-Y.; Fonari, A.; Tongwa, P.; Timofeeva, T.; Belfield, K.-D. J. Org. Chem. 2013, 78, 1014. doi: 10.1021/jo302423p
3. [3]
  Xu, H.-J.; 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
4. [4]
  Wu, J.-Y.; Liu, J.-L.; Zhou, T.-T.; Bo, S.-H.; Qiu, L.; Zhen, Z.; Liu, X.-H. RSC Adv. 2012, 2, 1416. doi: 10.1039/C1RA00838B
5. [5]
  Robinson, B.-H.; Dalton, L.-R.; Harper, A.-W. J. Mater. Sci.:Mater. Electron. 2014, 25, 3633. doi: 10.1007/s10854-014-2067-z
6. [6]
  Robinson, B.-H.; Dalton, L.-R.; Harper, A.-W. Chem. Phys. 1999, 245, 35. doi: 10.1016/S0301-0104(99)00079-8
7. [7]
  Wang, H.-R.; Liu, F.-G.; Yang, Y.-H. Dyes Pigm. 2015, 112, 42. doi: 10.1016/j.dyepig.2014.06.024
8. [8]
  Cho, B.-R.; Son, K.-N.; Lee, S.-J.; Kang, T.-I.; Han, M.-S.; Jeon, S.-J.; Song, N.-W.; Kim, D. Tetrahedron Lett. 1998, 39, 3167. doi: 10.1016/S0040-4039(98)00450-X
9. [9]
  Gong, W.; Li, Q.-Q.; Li, S.-Y.; Lu, C.-G.; Li, Z. Zhu, J.; Zhu, Z.-C.; Li, Z.-A.; Wang, Q.-R.; Cui, Y.-P.; Qin, J.-G. Mater. Lett. 2007, 61, 1151. doi: 10.1016/j.matlet.2006.06.070
10. [10]
  Tang, X.; Tang, X.-Z.; You, Y.-C.; Ren, L.-K.; Wang, Y.; Yan, L.-J. Acta Chim. Sinica 2012, 70, 1565(in Chinese). doi: 10.6023/A12030006
11. [11]
  Qiu, L.; Shen, Y.-Q.; Hao, J.-M.; Zhai, J.-F.; Zu, F.-H.; Zhang, T.; Zhao, Y.-X.; Clays, K.; Persoons, A. J. Mater. Sci. 2004, 39, 2335. doi: 10.1023/B:JMSC.0000019994.38191.fe
12. [12]
  Ashraf, M.; Teshome, A.; Kay, A.-J.; Gainsford, G.-J.; Bhuiyan, M.-D.; Asselberghs, I.; Clays, K. Dyes Pigm. 2012, 95, 455. doi: 10.1016/j.dyepig.2012.04.022
13. [13]
  Ashraf, M.; Teshome, A.; Kay, A.-J.; Gainsford, G.-J.; Bhuiyan, M.-D.; Asselberghs, I.; Clays, K. Dyes Pigm. 2013, 98, 82. doi: 10.1016/j.dyepig.2013.01.010
14. [14]
  Traskovskis, K.; Zarins, E.; Laipniece, L.; Tokmakovs, A.; Kokars, V.; Rutkis, M. Mater. Chem. Phys. 2015, 155, 232. doi: 10.1016/j.matchemphys.2015.02.035
15. [15]
  Hao, J.-M.; Han, M.-J.; Guo, K.-P.; Zhao, Y.-X.; Qiu, L.; Shen, Y.-Q.; Meng, X.-G. Mater. Lett. 2008, 62, 973. doi: 10.1016/j.matlet.2007.07.023
16. [16]
  Guo, K.-P.; Hao, J.-M.; Zhang, T.; Zu, F.-H.; Zhai, J.-F.; Qiu, L.; Zhen, Z.; Liu, X.-H.; Shen, Y.-Q. Dyes Pigm. 2008, 77, 657. doi: 10.1016/j.dyepig.2007.09.006
17. [17]
  Wang, Y.; Tang, X.-Z.; Tang, X. Chem. J. Chin. Univ. 2011, 32, 2327(in Chinese).
18. [18]
  Hua, J.-L.; Li, J.; Luo, J.-D. Chin. J. Org. Chem. 2003, 23(1), 44(in Chinese).
19. [19]
  Luo, J.-D.; Hua, J.-L.; Qin, J.-G.; Cheng, J.-Q.; Shen, Y.-C.; Lu, Z.-H.; Wang, P.; Ye, C. Chem. Commun. 2001, 171-172.
20. [20]
  Bosshard, C.; Knpfle, G.; Prêtre, P. J. Appl. Phys. 1992, 71, 1594. doi: 10.1063/1.351237
21. [21]
  Paley, M.; Harris, J. J. Polym. Sci. Part A:Polym. Chem. 1987, 25(9), 2447. doi: 10.1002/pola.1987.080250910
22. [22]
  Qian, Y.; Lin, B.-Q.; Xiao, G.-M. Opt. Mater. 2004, 27, 125-130. doi: 10.1016/j.optmat.2004.02.017
23. [23]
  Immirizi, A.; Perini, B. Acta Crystallogr. Sect. A 1977, 33, 216. doi: 10.1107/S0567739477000448
1. [1]
  Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO₂-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
2. [2]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
3. [3]
  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
4. [4]
  Lei ZHANG , Cheng HE , Yang JIAO . An azo-based fluorescent probe for the detection of hypoxic tumor cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1162-1172. doi: 10.11862/CJIC.20250081
5. [5]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
6. [6]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
7. [7]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
8. [8]
  Jiageng Li , Putrama . 数值积分耦合非线性最小二乘法一步确定反应动力学参数. University Chemistry, 2025, 40(6): 364-370. doi: 10.12461/PKU.DXHX202407098
9. [9]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
10. [10]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
11. [11]
  Shu'e Song , Xiaokui Wang , Yongmei Liu , Wanchun Zhu , Hong Yuan , Fuping Tian , Yunshan Bai , Yunchao Li , Li Wang , Zhongyun Wu , Yuan Chun , Jianrong Zhang , Shuyong Zhang . Suggestions on Operating Specifications of Physical Chemistry Experiment: Measurement of Viscosity, Density and Optical Properties. University Chemistry, 2025, 40(5): 148-156. doi: 10.12461/PKU.DXHX202503026
12. [12]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
13. [13]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
14. [14]
  Ying Xiong , Guangao Yu , Lin Wu , Qingwen Liu , Houjin Li , Shuanglian Cai , Zhanxiang Liu , Xingwen Sun , Yuan Zheng , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Determination of Physical Constants of Organic Compounds. University Chemistry, 2025, 40(5): 106-121. doi: 10.12461/PKU.DXHX202503079
15. [15]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
16. [16]
  Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
17. [17]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
18. [18]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
19. [19]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
20. [20]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1807)
HTML views(327)

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