ARTICLES

Synthesis of 2-(3-Cyanofuran-2(5H)-ylidene)malononitrile Derivative and Its Recognition for Pd2+

  • Keli Zhong ,
  • Lulu Zhou ,
  • Lin Chen ,
  • Lijun Tang ,
  • Xue Gao ,
  • Xiuying Liu ,
  • Xiuxiu Pang ,
  • Xiaomei Yan
Expand
  • a College of Chemistry and Material 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, Liaoning 116044
* Corresponding authors. E-mail: ;

Received date: 2020-08-25

  Revised date: 2020-11-03

  Online published: 2020-11-12

Supported by

National Natural Science Foundation of China(21878023); National Natural Science Foundation of China(U1608222); Natural Science Foundation of Liaoning Province(2020-MS-289); Natural Science Foundation of Liaoning Province(20180551195); Program for Distinguished Professor of Liaoning Province.

Abstract

2-(3-Cyano-furan-2(5H)-methylene)malononitrile derivative (TCF-Pyn) was synthesized by a two-step reaction. Compound TCF-Pyn could recognize Pd2+ with a high selectivity, “OFF-ON” fluorescent response and the near-infrared emission (653 nm) in MeCN/PBS ( VV=2∶8, PBS 2×10–2 mol/L, pH=7.4) solution. The probe possesses a good anti- interference capability, a wide pH range (3~8) and a low detection limit (6.92 μmol/L). The application research showed that TCF-Pyn could detect Pd2+ in real water samples and fluorescent image Pd2+in living cells.

Cite this article

Keli Zhong , Lulu Zhou , Lin Chen , Lijun Tang , Xue Gao , Xiuying Liu , Xiuxiu Pang , Xiaomei Yan . Synthesis of 2-(3-Cyanofuran-2(5H)-ylidene)malononitrile Derivative and Its Recognition for Pd2+[J]. Chinese Journal of Organic Chemistry, 2021 , 41(3) : 1124 -1130 . DOI: 10.6023/cjoc202008047

References

[1]
Jun, M. E.; Ahn, K. H. Org. Lett. 2010, 12, 2790.
[2]
Santra, M.; Ko, S. K.; Shin, I.; Ahn, K. H. Chem. Commun. 2010, 46, 3964.
[3]
Balamurugan, R.; Chien, C. C.; Wu, K. M.; Chiu, Y. H.; Liu, J. H. Analyst 2013, 138, 1564.
[4]
Chen, H.; Lin, W.; Yuan, L. Org. Biomol. Chem. 2013, 11, 1938.
[5]
Liu, B.; Wang, H.; Wang, T.; Bao, Y.; Du, F.; Tian, J.; Li, Q.; Bai, R. Chem. Commun. 2012, 48, 2867.
[6]
Sun, S.; Qiao, B.; Jiang, N.; Wang, J.; Zhang, S.; Peng, X. Org. Lett. 2014, 16, 1132.
[7]
Li, H.; Cao, J.; Zhu, H.; Fan, J.; Peng, X. Tetrahedron Lett. 2013, 54, 4357.
[8]
Kaur, V.; Aulakh, J. S.; Malik, A. K. Anal. Chim. Acta 2007, 603, 44.
[9]
Locatelli, C.; Melucci, D.; Torsi, G. Anal. Bioanal. Chem. 2005, 382, 1567.
[10]
Van, Meel, K.; Smekens,, A.; Behets,, M.; Kazandjian,, P.; Van, Grieken, R. Anal. Chem. 2007, 79, 6383.
[11]
Calvo Fornieles, A.; García de Torres, A.; Vereda Alonso, E.; Pavón, J. M. Microchem. J. 2016, 124, 82.
[12]
Tang, L.; Xia, J.; Zhong, K.; Tang, Y.; Gao, X.; Li, J. Dyes Pigm. 2020, 178, 108379.
[13]
Luo, X.; Li, J.; Zhao, J.; Gu, L.; Qian, X.; Yang, Y. Chin. Chem. Lett. 2019, 30, 839.
[14]
Yu, L.; Qiao, Y.; Miao, L.; He, Y.; Zhou, Y. Chin. Chem. Lett. 2018, 29, 1545.
[15]
Tang, L.; Zhou, L.; Yan, X.; Zhong, K.; Gao, X.; Li, J. J. Photochem. Photobiol., B 2020, 387, 112160.
[16]
Yang, B.; Xu, J.; Zhu, H.-L. Free Radicals Biol. Med. 2019, 145, 42.
[17]
Zhu, Z.; Liu, W.; Cheng, L.; Li, Z.; Xi, Z.; Yi, L. Tetrahedron Lett. 2015, 56, 3909.
[18]
Tang, L.; Zhou, L.; Yan, X.; Zhong, K.; Gao, X.; Liu, X.; Li, J. Dyes Pigm. 2020, 182, 108644.
[19]
Peng, R.; Xu, Y.; Cao, Q. Chin. Chem. Lett. 2018, 29, 1465.
[20]
Zhong, K.; He, Y.; Deng, L.; Ya, n X.; Li, X.; Tang, Y.; Hou, S.; Tang, L. Anal. Chim. Acta 2020, 1127, 49.
[21]
Gao, W.; Wang, W.; Yao, S.; Wu, S.; Zhang, H.; Zhang, J.; Jing, F.; Mao, H.; Jin, Q.; Cong, H. Anal. Chim. Acta 2017, 958, 77.
[22]
Liu, X.; Li, N.; Li, M.; Chen, H.; Zhang, N.; Wang, Y.; Zheng, K. Coord. Chem. Rev. 2020, 404, 213109.
[23]
Tang, Y.; Huang, Y.; Chen, Y.; Lu, L.; Wang, C.; Sun, T.; Wang, M.; Zhu, G.; Yang, Y.; Zhang, L. Spectrochim. Acta, Part A 2019, 218, 359.
[24]
Wang, D.; Fan, X.; Sun, S.; Du, S.; Li, H.; Zhu, J.; Tang, Y.; Chang, M.; Xu, Y. Sens. Actuators, B 2018, 264, 304.
[25]
Tang, Y.; Huang, Y.; Lu, L.; Wang, C.; Sun, T.; Zhu, J.; Zhu, G.; Pan, J.; Jin, Y.; Liu, A. Tetrahedron Lett. 2018, 59, 3916.
[26]
Wang, R.; Lai, X.; Qiu, G.; Liu, J. Chin. J. Org. Chem. 2019, 39, 952. (in Chinese)
[26]
(王瑞祥, 赖晓静, 邱观音生, 刘晋彪, 有机化学, 2019, 39, 952.)
[27]
Shi, Y.; Yu, Y.; Xue, L.; Wang, Y. Chin. J. Org. Chem. 2019, 39, 3414. (in Chinese)
[27]
(石岩, 于有伟, 薛林, 王延风, 有机化学, 2019, 39, 3414.)
[28]
Chen, S.; Pang, C.; Chen, X.; Yan, Z.; Huang, S.; Li, X.; Zhong, Y.; Wang, C. Chin. J. Org. Chem. 2019, 39, 1846. (in Chinese)
[28]
(陈思鸿, 庞楚明, 陈孝云, 严智浩, 黄诗敏, 李香弟, 钟雅婷, 汪朝阳, 有机化学, 2019, 39, 1846.)
[29]
Wang, Q.; Chen, Q.; Li, C.; Lai, Q.; Zou, F.; Liang, F.; Jiang, G.; Wang, J. Microchem. J. 2020, 153, 104503.
[30]
Tang, F. K.; Chan, S. M.; Wang, T.; Kwan, C. S.; Huang, R.; Cai, Z.; Leung, K. C. Talanta 2020, 210, 120634.
[31]
Soares-Paulino, A. A.; Giroldo, L.; Pradie, N. A.; Reis, J. S.; Back, D. F.; Braga, A. A. C.; Stefani, H. A.; Lodeiro, C.; Dos Santos, A. A. Dyes Pigm. 2020,179.
[32]
Dong, Z.; Chen, W.; Li, H.; Dai, Y.; Zheng, T.; Zhang, H.; Xu, H.; Lu, H. Inorg. Chem. Commun. 2020,116.
[33]
Zhang, X. P.; Yuan, Q.; Qi, Y. L.; Zheng, D. J.; Liu, Q. X.; Wang, B. Z.; Yang, Y. S.; Zhu, H. L. Spectrochim. Acta, Part A 2019, 220, 117134.
[34]
Yang, M.; Wang, L.; Leng, X.; Zhang, Y. Tetrahedron 2019, 75, 130570.
[35]
Su, K.; Ming, J.; Zhang, L.; Xiang, S.; Cui, M.; Yang, H. Opt. Mater. 2019, 93, 25.
[36]
Chen, X.-Z.; Ma, X.-D.; Wang, H.-M.; Wang, M.; Zhang, Y.-Y.; Gao, G.; Liu, J.-J.; Hou, S.-C. New J. Chem. 2017, 41, 8026.
[37]
Zhou, J.; Zhang, J.; Ren, H.; Dong, X.; Zheng, X.; Zhao, W. Chin. J. Chem. 2016, 34, 715.
[38]
Huang, Y.; Lei, L.; Zheng, C.; Wei, B.; Zhao, Z.; Qin, A.; Hu, R.; Tang, B. Acta Chim. Sinica 2016, 74, 885. (in Chinese)
[38]
(黄玉章, 雷洛奇, 郑超, 危博, 赵祖金, 秦安军, 胡蓉蓉, 唐本, 化学学报, 2016, 74, 885.)
[39]
Mondal, S.; Manna, S. K.; Pathak, S.; Masum, A. A.; Mukhopadhyay, S. New J. Chem. 2019, 43, 3513.
[40]
Luo, W.; Lei, M.; Wang, Y.; Gao, H.; Wang, Y.; Zhou, Q.; Xu, Z.; Yang, F. Anal. Methods 2019, 11, 1080.
[41]
Li, Y.; Yang, L.; Du, M.; Chang, G. Analyst 2019, 144, 1260.
[42]
Ke, B.; Chen, H.; Cui, Y.; Ma, L.; Liu, Y.; Hu, X.; Bai, Y.; Du, L.; Li, M. Talanta 2019, 194, 925.
[43]
Li, L.; Guan, R.; Guo, M.; Ning, P.; Shao, R.; Meng, X. Sens. Actuators, B 2018, 254, 949.
[44]
Kinska, K.; Jimenez-Lamana, J.; Kowalskay, J.; Krasnodebska- Ostrega, B.; Szpunar, J. Sci. Total Environ. 2018, 615, 1078.
[45]
Huo, B.; Du, M.; Gong, A.; Li, M.; Fang, L.; Shen, A.; Lai, Y.; Bai, X.; Yang, Y. Anal. Methods 2018, 10, 3475.
[46]
Huang, J.; Ding, Y.; Fu, H.; Chen, B.; Han, Y. New J. Chem. 2018, 42, 15587.
[47]
Feng, W.; Feng, G. Sens. Actuators, B 2018, 255, 2314.
[48]
Ding, Y.; Zhao, S.; Wang, Q.; Yu, X.; Zhang, W. Sens. Actuators, B 2018, 256, 1107.
[49]
Long, Y.; Bai, Y.; Zhou, J.; Yang, B. J. Photochem. Photobiol., A 2017, 332, 422.
[50]
Higashi, A.; Kishikawa, N.; Ohyama, K.; Kuroda, N. Tetrahedron Lett. 2017, 58, 2774.
[51]
Che, C.; Chen, X.; Wang, H.; Li, J.-Q.; Xiao, Y.; Fu, B.; Qin, Z. New J. Chem. 2018, 42, 12773.
[52]
Ashwin, B.; Sivaraman, G.; Stalin, T.; Yuvakkumar, R.; Muthu Mareeswaran, P. J. Photochem. Photobiol., B 2018, 183, 302.
[53]
Chen, T.; Wei, T.; Zhang, Z.; Chen, Y.; Qiang, J.; Wang, F.; Chen, X. Dyes Pigm. 2017, 140, 392.
[54]
Bhanja, A. K.; Mishra, S.; Das Saha, K.; Sinha, C. Dalton Trans 2017, 46, 9245.
[55]
Zhou, L.; Hu, S.; Wang, H.; Sun, H.; Zhang, X. Spectrochim. Acta, Part A 2016, 166, 25.
[56]
Chen, Y.; Zhang, M.; Han, Y.; Wei, J. RSC Adv. 2016, 6, 8380.
[57]
Chen, Y.; Chen, B.; Luo, D.; Cai, Y.; Wei, Y.; Han, Y. Tetrahedron Lett. 2016, 57, 1192.
[58]
Wu, H.; Yang, X.; Men, J.; Zhang, H.; Zhou, J. Anal. Sci. 2019, 35, 1305.
[59]
Wen, J.; Lv, Y.; Xia, P.; Liu, F.; Xu, Y.; Li, H.; Chen, S. S.; Sun, S. Bioorg. Med. Chem. 2018, 26, 931.
[60]
Zhong, K.; Chen, L.; Yan, X.; Tang, Y.; Hou, S.; Li, X.; Tang, L. Dyes Pigm. 2020, 182, 108656.
[61]
Zhong, K.; Chen, L.; Pan, Y.; Yan, X.; Hou, S.; Tang, Y.; Gao, X.; Li, J.; Tang, L. Spectrochim. Acta, Part A 2019, 221, 117135.
[62]
Zhong, K.; Zhao, J.; Li, Q.; Hou, S.; Tang, Y.; Bian, Y.; Tang, L. Chin. J. Org. Chem. 2018, 38, 1786. (in Chinese)
[62]
(钟克利, 赵杰, 李秋莹, 侯淑华, 汤轶伟, 边延江, 汤立军, 有机化学, 2018, 38, 1786.)
[63]
Zhong, K.; Guo, B.; Sun, X.; Zhou, X.; Zhang, Q.; Tang, L.; Zhang, X. Chin. J. Org. Chem. 2017, 37, 2002. (in Chinese)
[63]
(钟克利, 郭宝峰, 孙笑寒, 周雪, 张强, 汤立军, 张行荣, 有机化学, 2017, 37, 2002.)
[64]
Dhoun, S.; Kaur, I.; Kaur, P.; Singh, K. Dyes Pigm. 2017, 143, 361.
Outlines

/