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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 5: 1251 - 1256

DOI: https://doi.org/10.6023/cjoc201912026

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

  • Zhong Keli ,
  • Zhou Lulu ,
  • Deng Longlong ,
  • Tang Lijun ,
  • Gao Xue ,
  • Liu Xiuying ,
  • Yan Xiaomei
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  • 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 date: 2019-12-18

  Revised date: 2020-01-18

  Online 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.

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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 . DOI: 10.6023/cjoc201912026

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.
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