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]
  Huiying Xu , Minghui Liang , Zhi Zhou , Hui Gao , Wei Yi . Application of Quantum Chemistry Computation and Visual Analysis in Teaching of Weak Interactions. University Chemistry, 2025, 40(3): 199-205. doi: 10.12461/PKU.DXHX202407011
2. [2]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
3. [3]
  Qingjun PAN , Zhongliang GONG , Yuwu ZHONG . Advances in modulation of the excited states of photofunctional iron complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 45-58. doi: 10.11862/CJIC.20240365
4. [4]
  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
5. [5]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
6. [6]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
7. [7]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
8. [8]
  Yingran Liang , Fei Wang , Jiabao Sun , Hongtao Zheng , Zhenli Zhu . Construction and Application of a New Experimental Device for Determination of Alkaline Metal Elements by Plasma Atomic Emission Spectrometry Based on Solution Cathode Glow Discharge: An Alternative Approach for Fundamental Teaching Experiments in Emission Spectroscopy. University Chemistry, 2024, 39(5): 380-387. doi: 10.3866/PKU.DXHX202312024
9. [9]
  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
10. [10]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
11. [11]
  Yue Wu , Jun Li , Bo Zhang , Yan Yang , Haibo Li , Xian-Xi Zhang . Research on Kinetic and Thermodynamic Transformations of Organic-Inorganic Hybrid Materials for Fluorescent Anti-Counterfeiting Application information: Introducing a Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(6): 390-399. doi: 10.3866/PKU.DXHX202403028
12. [12]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
13. [13]
  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
14. [14]
  Zijuan LI , Xuan LÜ , Jiaojiao CHEN , Haiyang ZHAO , Shuo SUN , Zhiwu ZHANG , Jianlong ZHANG , Yanling MA , Jie LI , Zixian FENG , Jiahui LIU . Synthesis of visual fluorescence emission CdSe nanocrystals based on ligand regulation. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 308-320. doi: 10.11862/CJIC.20240138
15. [15]
  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
16. [16]
  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
17. [17]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
18. [18]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
19. [19]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
20. [20]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(909)
HTML views(163)

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