Citation: Qin Xiaozhuan, Wang Xinchao, Feng Dandan, He Jiabei, Zheng Liping, Wang Yong, Xie Guanghui, Li Jingjing, Ding Ge. Study on Properties of Excited-state Intermolecular Proton Transfer (ESPT) Reaction Dendrite Containing Benzidine Fragments of Organic Chromophore[J]. Acta Chimica Sinica, ;2019, 77(8): 751-757. doi: 10.6023/A19040109 shu

Study on Properties of Excited-state Intermolecular Proton Transfer (ESPT) Reaction Dendrite Containing Benzidine Fragments of Organic Chromophore

Qin Xiaozhuan ^a,, ,
Wang Xinchao ^b,, ,
Feng Dandan ^a ,
He Jiabei ^c ,
Zheng Liping ^a ,
Wang Yong ^a ,
Xie Guanghui ^a ,
Li Jingjing ^a ,
Ding Ge ^d,,

a.
Zhengzhou Institute of Technology, School of Chemical Engineering & Food Science, Zhengzhou 450044
b.
Heze University, College of Parmacy, Heze 274015
c.
International College of Zhengzhou University, Zhengzhou 450000
d.
College of Materials and Chemical Engineering, Chongqing University of Arts and Sciences, Chongqing 402160

Corresponding author: Qin Xiaozhuan, xiaozhuanqin@163.com Wang Xinchao, wxc198566@126.com Ding Ge, dingge1989cqu@126.com
Received Date: 1 April 2019
Available Online: 12 August 2019
Fund Project: Project supported by the Department of Science and Technology of Henan Province (No. 192102210201) and the Youth Innovation Fund of Zhengzhou Institute of Technology (No. QNCXJJ2018K3)the Department of Science and Technology of Henan Province 192102210201the Youth Innovation Fund of Zhengzhou Institute of Technology QNCXJJ2018K3

Figures(9)

In this paper, the intermediates 2'-hydroxybiphenyl-2-amine (I1) and 2'-methoxybiphenyl-2-amine (I2) were first synthetized via Suzuki reaction of 2-bromoaniline and arylboronic acid under 80℃. Meanwhile, organic dyes benzidine fragments ((E)-2'-(2-nitrobenzylideneamino)-biphenyl-3-ol (C1) and (E)-2'-(2, 4-dinitrobenzylideneamino)-biphenyl-3-ol (C3)) which could undergo intermolecular proton transfer in excited states were synthetized via aminoaldehyde condensation of the intermediates biphenyl-2-amine and corresponding aldehyde. In addition, the dyes without proton transfer segments ((E)-2'-methoxy-N-(2-nitrobenzylidene)biphenyl-3-amine (C2) and (E)-2'-methoxy-N-(2, 4-dinitrobenzylidene)biphenyl-3-amine (C4)) were also synthesized to act as references for comparisons experiment. The chemical structures of organic dyes were characterized by nuclear magnetic resonance (NMR) spectra, infrared spectra (IR), high resolution mass spectrometry (HR-MS) as well as elemental analysis. The analysis of X-ray single crystal diffraction and H NMR spectra suggest the presence of internal hydrogen bond with different strength in the target dyes C1 and C3. It indicated that the type of substituents has an effect on the chemical shift of hydroxyl groups, with the electron-withdrawing ability of substituents increases, the hydroxyl shift to higher field. Then the UV/visible spectra also confirm that the target dyes have intermolecular hydrogen bond, while there is no intermolecular hydrogen bond in the reference dyes C2 and C4. The excited-state intermolecular proton transfer (ESPT) properties of the organic dyes were further studied by fluorescence emission spectroscopy. It was found that target dye C3 could occur excited state intermolecular proton transfer (ESPT) via intermolecular hydrogen bonding in non-protonic solvents. In contrast, ESPT properties cannot be processed through hydrogen-bonding interaction of the studied target dye C1 no matter in protonic solvents, non-protonic solvents or in solid state. The target dye C1 and reference dyes (C2 and C4) only show the normal fluorescence emission peaks. It was worth mentioning that with the increasing concentration of C3 in solution, the ESPT reaction ability could be enhanced. Meanwhile, C3 can also occurs ESPT in solid state.
- hydrogen bond,
- proton transfer,
- organic chromophore,
- excited-state,
- fluorescence emission spectroscopy
1. [1]
  Ayad, S.; Posey, V.; Das, A.; Montgomery, J. M.; Hanson, K. Chem. Commun. 2019, 55(9), 1263. doi: 10.1039/C8CC07949H
2. [2]
  Li, P.; Zeng, Y.; Chen, J. P.; Li, Y. Y.; Li, Y. Acta Chim. Sinica 2012, 70, 1611.
3. [3]
  Zhang, P.; Zhang, Y. M.; Lin, Q.; Yao, H.; Wei, T. B. Chin. J. Org. Chem. 2014, 34, 1300.
4. [4]
  Sedgwick, A. C.; Wu, L. L.; Han, H. H.; Bull, S. D.; He, X. P.; James, T. D.; Sessler, J. L.; Tang, B. Z.; Tian, H.; Yoon, J. Y. Chem. Soc. Rev. 2018, 47(23), 8842. doi: 10.1039/C8CS00185E
5. [5]
  Wang, M.; Cheng, C.; Song, J.; Wang, J.; Zhou, X.; Xiang, H.; Liu, J. Chinese J. Chem. 2018, 36, 698. doi: 10.1002/cjoc.201800115
6. [6]
  Pan, S. N.; Tang, H. Y.; Song, Z. K.; Li, J.; Guo, Y. Chinese J. Chem. 2017, 35, 1263. doi: 10.1002/cjoc.201600923
7. [7]
  Wu, K.; Zhang, T.; Wang, Z.; Wang, L.; Zhan, L.; Zhan, L. S.; Gong, S. L.; Zhong, C.; Lu, Z. H.; Zhang, S.; Yang, C. L. J. Am. Chem. Soc. 2018, 140, 8877. doi: 10.1021/jacs.8b04795
8. [8]
  Serdiuk, I. E.; Roshal, A. D. Dyes Pigments 2017, 138, 223. doi: 10.1016/j.dyepig.2016.11.028
9. [9]
  Simkovitch, R.; Kisin-Finfer, E.; Shomer, S.; Gepshtein, R.; Shabat, D.; Huppert, D. J. Photoch. Photobio. A 2013, 254, 45. doi: 10.1016/j.jphotochem.2013.01.004
10. [10]
  Fernandez-Ramos, A.; Martinez-Nunez, E.; Vazquez, S. A.; Rios, M. A.; Estevez, C. M.; Merchan, M.; Serrano-Andres, L. J. Phys. Chem. A 2007, 111(26), 5907.
11. [11]
  Hsu, S. C.; Wang, T. P.; Kao, C. L.; Chen, H. F.; Yang, P. Y.; Chen, H. Y. J. Phys. Chem. B 2013, 117(7), 2096. doi: 10.1021/jp400299v
12. [12]
  Yokoyama, H.; Watanabe, H.; Omi, T.; Ishiuchi, S. I.; Fujii, M. J. Phys. Chem. A 2001, 105(41), 9366. doi: 10.1021/jp011245g
13. [13]
  Zhao, L.; Liu, J.; Zhou, P. J. Phys. Chem. A 2016, 120, 7419. doi: 10.1021/acs.jpca.6b05719
14. [14]
  Yokoyama, H.; Watanabe, H.; Omi, T.; Ishiuchi, S. I.; Fujii, M. J. Phys. Chem. A 2001, 105(41), 9366. doi: 10.1021/jp011245g
15. [15]
  Fang, H. Spectrochim. Acta A 2019, 214, 152. doi: 10.1016/j.saa.2019.02.016
16. [16]
  Wang, D. J.; Xu, Y. Q.; Sun, S. G.; Li, H. J. Chin. J. Appl. Chem. 2018, 35(1), 1.
17. [17]
  Qin, X. Z.; Li, G.; Wang, Z. Q.; Ding, G..; Luo, Z. P.; Li, H. R.; Chen, L. Y.; Gao, F. Dyes Pigments 2017, 145, 538. doi: 10.1016/j.dyepig.2017.06.055
18. [18]
  Wang, Y.; Li, M.; Zhang, Y.; Yang, J.; Zhu, S.; Sheng, L.; Zhang, S. X. A. Chem. Commun. 2013, 49(59), 6587. doi: 10.1039/C3CC42747A
19. [19]
  Casanovas, J.; Namba, A. M.; León, S.; Aquino, G. L.; da Silva, G. V. J.; Alemán, C. J. Org. Chem. 2001, 66, 3775. doi: 10.1021/jo0016982
20. [20]
  Yi, P. G.; Yang, X. C.; Liu, J.; Hou, B.; Yu, X. Y.; Li, X. F.; Wang, Z. X.; Zheng, B. S. Chin. J. Org. Chem. 2013, 33, 1451.
21. [21]
  Ingham, K.; El-Bayoumi, M. A. J. Am. Chem. Soc. 1974, 96(6), 1674. doi: 10.1021/ja00813a006
22. [22]
  Parada, G. A.; Markle, T. F.; Glover, S. D.; Hammarström, L.; Ott, S.; Zietz, B. Chem.-Eur. J. 2015, 21, 6362. doi: 10.1002/chem.201500244
23. [23]
  Qin, T. Y.; Zeng, Y.; Chen, J. P.; Yu, T. J.; Li, Y. Acta Chim. Sinica 2017, 75, 1164. doi: 10.3969/j.issn.0253-2409.2017.10.002
24. [24]
  Doroshenko, A. O.; Posokhov, E. A.; Verezubova, A. A.; Ptyagina, L. M. J. Phys. Org. Chem. 2000, 13, 253. doi: 10.1002/1099-1395(200005)13:5<253::AID-POC238>3.0.CO;2-D
25. [25]
  Mehata, M. S.; Joshi, H. C.; Tripathi, H. B. Chem. Phys. Lett. 2002, 359(3-4), 314. doi: 10.1016/S0009-2614(02)00716-9
26. [26]
  Bulska, H.; Chodkowska, A. J. Am. Chem. Soc. 1980, 102(9), 3259. doi: 10.1021/ja00529a069
1. [1]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
2. [2]
  Yinglian LI , Chengcheng ZHANG , Xinyu ZHANG , Xinyi WANG . Spin crossover in [Co(pytpy)₂]²⁺ complexes modified by organosulfonate anions. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1162-1172. doi: 10.11862/CJIC.20240087
3. [3]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
4. [4]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
5. [5]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
6. [6]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
7. [7]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
8. [8]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
9. [9]
  Qiuyang LUO , Xiaoning TANG , Shu XIA , Junnan LIU , Xingfu YANG , Jie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110
10. [10]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414
11. [11]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
12. [12]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
13. [13]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
14. [14]
  Liang MA , Honghua ZHANG , Weilu ZHENG , Aoqi YOU , Zhiyong OUYANG , Junjiang CAO . Construction of highly ordered ZIF-8/Au nanocomposite structure arrays and application of surface-enhanced Raman spectroscopy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1743-1754. doi: 10.11862/CJIC.20240075
15. [15]
  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
16. [16]
  Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C₃N₄ nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
17. [17]
  Huan LI , Shengyan WANG , Long Zhang , Yue CAO , Xiaohan YANG , Ziliang WANG , Wenjuan ZHU , Wenlei ZHU , Yang ZHOU . Growth mechanisms and application potentials of magic-size clusters of groups Ⅱ-Ⅵ semiconductors. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1425-1441. doi: 10.11862/CJIC.20240088
18. [18]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
19. [19]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
20. [20]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(772)
HTML views(141)

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