Synthesis of Novel 7-Hydroxytetrahydroquinoxaline-6-formaldehyde Acylhydrazone Derivative and Its Recognition for Al3+

doi:10.6023/cjoc201912026

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1251-1256.DOI: 10.6023/cjoc201912026 Previous Articles Next Articles

新型7-羟基四氢喹喔啉-6-甲醛酰腙衍生物的合成及其对Al³⁺的识别

钟克利^a, 周璐璐^a, 邓隆隆^a, 汤立军^a, 高雪^b, 刘秀英^b, 燕小梅^c

a 渤海大学化学化工学院辽宁锦州 121013;
b 渤海大学食品科学与工程学院生鲜农产品贮藏加工及安全控制技术国家地方联合工程研究中心辽宁锦州 121013;
c 大连医科大学检验医学院大连 116044

收稿日期:2019-12-18 修回日期:2020-01-18 发布日期:2020-01-21
通讯作者: 汤立军, 燕小梅 E-mail:ljtang@bhu.edu.cn;xmyan1978@sina.com
基金资助:
国家自然科学基金（Nos.21878023，U1608222）、辽宁省自然科学基金（No.20180551195）、辽宁省教育厅科学研究基金（No.LJ2019005）、辽宁省高等学校基本科研项目（No.LQ2017048）、辽宁省特聘教授支持计划资助项目.

Synthesis of Novel 7-Hydroxytetrahydroquinoxaline-6-formaldehyde Acylhydrazone Derivative and Its Recognition for Al³⁺

Zhong Keli^a, Zhou Lulu^a, Deng Longlong^a, Tang Lijun^a, Gao Xue^b, Liu Xiuying^b, Yan Xiaomei^c

a College of Chemistry and Chemical Engineering, Bohai University, Jinzhou, Liaoning 121013;
b National & Local Joint Engineering Research Center of Storage, Processing and Safety Control Technology for Fresh Agricultural and Aquatic Products, College of Food Science and Technology, Bohai University, Jinzhou, Liaoning 121013;
c College of Laboratory Medicine, Dalian Medical University, Dalian 116044

Received:2019-12-18 Revised:2020-01-18 Published:2020-01-21
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21878023, U1608222), the Natural Science Foundation of Liaoning Province (No. 20180551195), the Scientific Research Fund of Liaoning Provincial Education Department (No. LJ2019005), the Basic Research Projects for Undergraduate College of Liaoning Province (No. LQ2017048), and the Program for Distinguished Professor of Liaoning Province.

1. 201251S.pdf(618KB)

Abstract

A novel acylhydrazone derivative (i.e. fluorescence probe L) was designed and synthesized based on 7-hydroxy- tetrahydroquinoxaline-6-formaldehyde. Probe L can recognize for Al³⁺ with highly selectivity in DMSO/Tris (V:V=7:3) solution. When Al³⁺ is added into the solution of L, the fluorescence color of solution changes from non-fluorescence to purple red fluorescence, and the maximum emission wavelength of L is 640 nm within range of the near-infrared. Probe L possesses a large Stokes shift (170 nm) and the detection limit of L is 0.521 μmol/L. In addition, L can detect Al³⁺ in the real water samples and imaging for Al³⁺ in MCF-7 cells.

Key words: 7-hydroxytetrahydroquinoxaline-6-formaldehyde, fluorescent probe, Al³⁺, recognition, cell imaging

Cite this article

Zhong Keli, Zhou Lulu, Deng Longlong, Tang Lijun, Gao Xue, Liu Xiuying, Yan Xiaomei. Synthesis of Novel 7-Hydroxytetrahydroquinoxaline-6-formaldehyde Acylhydrazone Derivative and Its Recognition for Al³⁺[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1251-1256.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Shellaiah, M.; Wu, Y. H.; Lin, H. C. Analyst 2013, 138, 2931.
[2] Naskar, B.; Modak, R.; Sikdar, Y.; Maiti, D. K.; Bauzá, A.; Frontera, A.; Katarkar, A.; Chaudhuri, K.; Goswami, S. Sens. Actuators, B 2017, 239, 1194.
[3] Irimia-Vladu, M. Chem. Soc. Rev. 2014, 43, 588.
[4] Han, T.; Feng, X.; Tong, B.; Shi, J.; Chen, L.; Zhi, J.; Dong, Y. Chem. Commun. 2012, 48, 416.
[5] Gui, S.; Huang, Y.; Hu, F.; Jin, Y.; Zhang, G.; Yan, L.; Zhang, D.; Zhao, R. Anal. Chem. 2015, 87, 1470.
[6] Das, S.; Sahana, A.; Banerjee, A.; Lohar, S.; Safin, D. A.; Babashkina, M. G.; Bolte, M.; Garcia, Y.; Hauli, I.; Mukhopadhyay, S. K.; Das, D. Dalton Trans. 2013, 42, 4757.
[7] Vallejos, S.; Munoz, A.; Ibeas, S.; Serna, F.; Garcia, F. C.; Garcia, J. M. ACS Appl. Mater. Interfaces 2015, 7, 921.
[8] Mirza, A.; King, A.; Troakes, C.; Exley, C. J. Trace Elem. Med. Biol. 2017, 40, 30.
[9] House, E.; Esiri, M.; Forster, G.; Ince, P. G.; Exley, C. Metallomics 2012, 4, 56.
[10] Chen, Y. C.; Lee, I. L.; Sung, Y. M.; Wu, S. P. Talanta 2013, 117, 70.
[11] Lian, H.; Kang, Y.; Bi, S.; Arkin, Y.; Shao, D.; Li, D.; Chen, Y.; Dai, L.; Gan, N.; Tian, L. Talanta 2004, 62, 43.
[12] Ahmed, M. J.; Hossan, J. Talanta 1995, 42, 1135.
[13] Sen, B.; Pal, S.; Lohar, S.; Mukherjee, M.; Mandal, S. K.; Khuda- Bukhsh, A. R.; Chattopadhyay, P. RSC Adv. 2014, 4, 21471.
[14] Zhong, K.; Deng, L.; Zhao, J.; Yan, X.; Sun, T.; Li, J.; Tang, L. RSC Adv. 2018, 8, 23924.
[15] Wang, R.; Lai, X.; Qiu, G.; Liu, J. Chin. J. Org. Chem. 2019, 39, 952(in Chinese). (王瑞祥, 赖晓静, 邱观音生, 刘晋彪, 有机化学, 2019, 39, 952.)
[16] Tang, L.; Tian, M.; Chen, H.; Yan, X.; Zhong, K.; Bian, Y. Dyes Pigm. 2018, 158, 482.
[17] Tang, L.; He, P.; Yan, X.; Sun, J.; Zhong, K.; Hou, S.; Bian, Y. Sens. Actuators, B 2017, 247, 421.
[18] Neeraj; Kumar, A.; Asthana, S. K.; Shweta; Upadhyay, K. K. J. Photochem. Photobiol., A 2016, 329, 69.
[19] Ma, T.; Zhang, J.; Liu, L.; He, Y.; Zhang, Z. Chin. J. Org. Chem. 2014, 34, 1780(in Chinese). (马拓, 张瑾, 刘龙珠, 贺云, 张尊听, 有机化学, 2014, 34, 1780.)
[20] Liu, X.; Qi, F.; Su, Y.; Chen, W.; Yang, L.; Song, X. J. Mater. Chem. C 2016, 4, 4320.
[21] Li, M. X.; Zhang, X.; Fan, Y. H.; Bi, C. F. Luminescence 2016, 31, 851.
[22] Jagtap, A. R.; Satam, V. S.; Rajule, R. N.; Kanetkar, V. R. Dyes Pigm. 2009, 82, 84.
[23] Hou, P.; Chen, S.; Wang, H.; Wang, J.; Voitchovsky, K.; Song, X. Chem. Commun. 2014, 50, 320
[24] Fu, J.; Chang, Y.; Li, B.; Mei, H.; Yang, L.; Xu, K. Analyst 2019, 144, 5706.
[25] Fu, J.; Yao, K.; Chang, Y.; Li, B.; Yang, L.; Xu, K. Spectrochim. Acta A 2019, 222, 117234.
[26] Luo, X.; Li, X.; Wang, Y.; Xie, X.; Yang, L. ChemistrySelect 2019, 4, 10643.
[27] Fu, J.; Li, B.; Mei, H.; Chang, Y.; Xu, K. Spectrochim. Acta, Part A 2020, 227, 117678.
[28] Dhaka, G.; Kaur, N.; Singh, J. J. Fluoresc. 2017, 27, 1943.
[29] Dey, S.; Maity, A.; Shyamal, M.; Das, D.; Maity, S.; Giri, P. K.; Mudi, N.; Samanta, S. S.; Hazra, P.; Misra, A. Photochem. Photobiol. Sci. 2019, 18, 2717.
[30] Li, Z.; Dai, F.; Wang, J.; Wang, S.; Xiao, L.; Li, L. Synth. Met. 2020, 259, 116234.
[31] Aydin, D. Talanta 2020, 210, 120615.
[32] Datta, B. K.; Thiyagarajan, D.; Kar, C.; Ramesh, A.; Das, G. Anal. Chim. Acta 2015, 882, 76.
[33] Liu, C.; Liu, L. M.; Li, T. R.; Liu, K.; Yang, Z. Y. Inorg. Chim. Acta 2020, 502, 119327.
[34] Sinha, S.; Chowdhury, B.; Ghosh, P. Inorg. Chem. 2016, 55, 9212.
[35] Chen, Y.; Wei, T.; Zhang, Z.; Chen, T.; Li, J.; Qiang, J.; Lv, J.; Wang, F.; Chen, X. Ind. Eng. Chem. Res. 2017, 56, 12267.
[36] Sahana, A.; Banerjee, A.; Lohar, S.; Sarkar, B.; Mukhopadhyay, S. K.; Das, D. Inorg. Chem. 2013, 52, 3627.

新型7-羟基四氢喹喔啉-6-甲醛酰腙衍生物的合成及其对Al³⁺的识别

Synthesis of Novel 7-Hydroxytetrahydroquinoxaline-6-formaldehyde Acylhydrazone Derivative and Its Recognition for Al³⁺

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[2]	Yingzhen Zhang, Dandan Jiang, Juanhua Li, Jingjing Wang, Kunming Liu, Jinbiao Liu. Construction Strategy and Imaging of Highly Selective Selenocysteine Fluorescent Probes [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 41-53.
[3]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[4]	Binghui Ding, Shaohui Han, Haiqing Xiong, Benhua Wang, Bojun Zuo, Xiangzhi Song. A Highly Selective Ratiometric Fluorescent Probe for the Detection of Hypochlorite in Acute Lung Injury [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2878-2884.
[5]	Tiantian Liu, Hongpeng Zhang, Xiaomeng Jiao, Yinjuan Bai. Research Progress of Multi-signal Fluorescent Probes for Simultaneous Detection of Biothiols [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2081-2095.
[6]	Yifang Li, Yao Wang, Huawei Niu, Xiujin Chen, Zhaozhou Li, Yongguo Wang. Research Progress of Sulfur Dioxide Fluorescent Probe Targeting Mitochondria [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1952-1962.
[7]	Yang Zhao, Panpan Chen, Gaonan Li, Zhigang Niu, Enju Wang. Tetraarylimidazole-Based Aggregation-Induced Emission Luminogens and Their Cell-Imaging Application [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2156-2162.
[8]	Feiran Liu, Jing Jing, Xiaoling Zhang. Research Progress of Fluorescent Probes for Cysteine Targeting Cellular Organelles [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2053-2067.
[9]	Zhihua Chen, Yan Hu, Lili Ma, Ziyi Zhang, Chuanxiang Liu. Rational Design of ortho-Vinylhydropyridine-Assisted Amino-fluorophore as Hypochlorite Fluorescent Probe [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 718-724.
[10]	Hongwei Tang, Chao Wang, Keli Zhong, Shuhua Hou, Lijun Tang, Yanjiang Bian. A Naked-Eye and Fluorescent Dual-Channel Probe for Rapid Detection of Hg²⁺ and Its Multiple Applications [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 712-717.
[11]	Huiming Lu, Lamaocao Ma, Hengchang Ma. Research Progress and Prospect of Aggregation-Induced Emission Supramolecular Luminescence Materials [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4075-4105.
[12]	Yanhui Ma, Yuqian Wu, Xiaoxu Wang, Gui Gao, Xin Zhou. Research Progress of Near-Infrared Fluorescent Probes Based on 1,3-Dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone (DDAO) [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 94-111.
[13]	Yaxin Yang, Lin Chen, Xiaoling Hu, Keli Zhong, Shidi Li, Xiaomei Yan, Jinglin Zhang, Lijun Tang. Synthesis of a Turn-On Fluorescent Probe for Hydrogen Sulfide and Its Application in Red Wine and Living Cells [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 308-312.
[14]	Meng Liu, Yanru Huang, Xiaofei Sun, Lijun Tang. An “Aggregation-Induced Emission+Excited-State Intramolecular Proton Transfer” Mechanisms-Based Benzothiazole Derived Fluorescent Probe and Its ClO^–Recognition [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 345-351.
[15]	Yangyang Li, Xiaofei Sun, Xiaoling Hu, Yuanyuan Ren, Keli Zhong, Xiaomei Yan, Lijun Tang. Synthesis of Triphenylamine Derivative and Its Recognition for Hg²⁺ with “OFF-ON” Fluorescence Response Based on Aggregation-Induced Emission (AIE) Mechanism [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 320-325.

新型7-羟基四氢喹喔啉-6-甲醛酰腙衍生物的合成及其对Al3+的识别