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

doi:10.6023/A19040109

Acta Chim. Sinica ›› 2019, Vol. 77 ›› Issue (8): 751-757.DOI: 10.6023/A19040109 Previous Articles Next Articles

Article

枝状含联苯胺基片段的有机生色团的激发态分子间质子转移性质研究

秦小转^a, 王新潮^b, 冯丹丹^a, 贺加贝^c, 郑丽萍^a, 王勇^a, 谢光辉^a, 李靖靖^a, 丁戈^d

a 郑州工程技术学院化工食品学院郑州 450044;
b 菏泽学院药学院菏泽 274015;
c 郑州大学国际学院郑州 450000;
d 重庆文理学院化学化工学院重庆 402160

投稿日期:2019-04-01 发布日期:2019-07-12
通讯作者: 秦小转, 王新潮, 丁戈 E-mail:xiaozhuanqin@163.com;wxc198566@126.com;dingge1989cqu@126.com
基金资助:
项目受河南省科技攻关项目（No.192102210201）和郑州工程技术学院青年创新基金（No.QNCXJJ2018K3）资助.

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

Received:2019-04-01 Published:2019-07-12
Contact: 10.6023/A19040109 E-mail:xiaozhuanqin@163.com;wxc198566@126.com;dingge1989cqu@126.com
Supported by:
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).

1. Study on Properties of Excited-state Intermolecular Proton Transfer (ESPT) Reaction Dendrite Containing Benzidine Fragments of Organic Chromophore.PDF(1533KB)

Abstract

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.

Key words: hydrogen bond, proton transfer, organic chromophore, excited-state, fluorescence emission spectroscopy

Cite this article

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 Chim. Sinica, 2019, 77(8): 751-757.

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[1] Ayad, S.; Posey, V.; Das, A.; Montgomery, J. M.; Hanson, K. Chem. Commun. 2019, 55(9), 1263.
[2] Li, P.; Zeng, Y.; Chen, J. P.; Li, Y. Y.; Li, Y. Acta Chim. Sinica 2012, 70, 1611. (李鹏, 曾毅, 陈金平, 李迎迎, 李嫕, 化学学报, 2012, 70, 1611.)
[3] Zhang, P.; Zhang, Y. M.; Lin, Q.; Yao, H.; Wei, T. B. Chin. J. Org. Chem. 2014, 34, 1300. (张鹏, 张有明, 林奇, 姚虹, 魏太保, 有机化学, 2014, 34, 1300)
[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.
[5] Wang, M.; Cheng, C.; Song, J.; Wang, J.; Zhou, X.; Xiang, H.; Liu, J. Chinese J. Chem. 2018, 36, 698.
[6] Pan, S. N.; Tang, H. Y.; Song, Z. K.; Li, J.; Guo, Y. Chinese J. Chem. 2017, 35, 1263.
[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.
[8] Serdiuk, I. E.; Roshal, A. D. Dyes Pigments 2017, 138, 223.
[9] Simkovitch, R.; Kisin-Finfer, E.; Shomer, S.; Gepshtein, R.; Shabat, D.; Huppert, D. J. Photoch. Photobio. A 2013, 254, 45.
[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] 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.
[12] Yokoyama, H.; Watanabe, H.; Omi, T.; Ishiuchi, S. I.; Fujii, M. J. Phys. Chem. A 2001, 105(41), 9366.
[13] Zhao, L.; Liu, J.; Zhou, P. J. Phys. Chem. A 2016, 120, 7419.
[14] Yokoyama, H.; Watanabe, H.; Omi, T.; Ishiuchi, S. I.; Fujii, M. J. Phys. Chem. A 2001, 105(41), 9366.
[15] Fang, H. Spectrochim. Acta A 2019, 214, 152.
[16] Wang, D. J.; Xu, Y. Q.; Sun, S. G.; Li, H. J. Chin. J. Appl. Chem. 2018, 35(1), 1. (王德佳, 徐勇前, 孙世国, 李红娟, 应用化学, 2018, 35(1), 1)
[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.
[18] Wang, Y.; Li, M.; Zhang, Y.; Yang, J.; Zhu, S.; Sheng, L.; Zhang, S. X. A. Chem. Commun. 2013, 49(59), 6587.
[19] Casanovas, J.; Namba, A. M.; León, S.; Aquino, G. L.; da Silva, G. V. J.; Alemán, C. J. Org. Chem. 2001, 66, 3775.
[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. (易平贵, 阳习春, 刘金, 侯博, 于贤勇, 李筱芳, 汪朝旭, 郑柏树, 有机化学, 2013, 33, 1451)
[21] Ingham, K.; El-Bayoumi, M. A. J. Am. Chem. Soc. 1974, 96(6), 1674.
[22] Parada, G. A.; Markle, T. F.; Glover, S. D.; Hammarström, L.; Ott, S.; Zietz, B. Chem.-Eur. J. 2015, 21, 6362.
[23] Qin, T. Y.; Zeng, Y.; Chen, J. P.; Yu, T. J.; Li, Y. Acta Chim. Sinica 2017, 75, 1164. (秦天依, 曾毅, 陈金平, 于天君, 李嫕, 化学学报, 2017, 75, 1164.)
[24] Doroshenko, A. O.; Posokhov, E. A.; Verezubova, A. A.; Ptyagina, L. M. J. Phys. Org. Chem. 2000, 13, 253.
[25] Mehata, M. S.; Joshi, H. C.; Tripathi, H. B. Chem. Phys. Lett. 2002, 359(3-4), 314.
[26] Bulska, H.; Chodkowska, A. J. Am. Chem. Soc. 1980, 102(9), 3259.

枝状含联苯胺基片段的有机生色团的激发态分子间质子转移性质研究

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

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