Citation: SHEN Zhong-Hua, SHI Yan-Xia, YANG Ming-Yan, SUN Zhao-Hui, WENG Jian-Quan, TAN Cheng-Xia, LIU Xing-Hai, LI Bao-Ju, ZHAO Wei-Guang. Synthesis, Crystal Structure, DFT Studies and Biological Activity of a Novel Schiff Base Containing Triazolo[4,3-a]pyridine Moiety[J]. Chinese Journal of Structural Chemistry, ;2016, 35(3): 457-464. doi: 10.14102/j.cnki.0254-5861.2011-0913 shu

Synthesis, Crystal Structure, DFT Studies and Biological Activity of a Novel Schiff Base Containing Triazolo[4,3-a]pyridine Moiety

1.
a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China;
2.
b Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing 100014, China;
3.
c Collaborative Innovation Center of Chemical Science and Engineering, State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: LIU Xing-Hai, LI Bao-Ju,
Received Date: 28 July 2015
Available Online: 6 November 2015
Fund Project: This work was funded by National Natural Science Foundation of China (No.21002090) (No.21002090) Zhejiang Provincial Natural Science Foundation of China (No. LY16C140007) (No. LY16C140007)D Program (2011BAE06B03-01) (2011BAE06B03-01)

The novel Schiff base (E)-8-chloro-N'-(4-(dimethylamino)benzylidene)-[1, 2, 4]tria-zolo[4, 3-a]pyridine-3-carbohydrazide was synthesized and characterized by ¹H NMR, MS, elemental analysis and X-ray diffraction. The compound crystallizes in the monoclinic space group P2₁/c with a = 7.091(2), b = 10.750(3), c = 21.380(6) Å, β = 96.299(6)°, V = 1619.7(8) Å³, Z = 4 and R = 0.0351. Theoretical calculation of the title compound was carried out with the B3LYP/6-31G basis set. The frontier orbital energy and atomic net charges were discussed. It is found that the experimental data show good agreement with the calculated values. And the compound exhibits good antifungal activity against Stemphylium lycopersici (Enjoji) Yamamoto.
- 1,2,4-triazolo[4,3-a]pyridine,
- hydrazine,
- synthesis,
- crystal structure,
- theoretical calculation,
- antifungal activity
1. [1]
  (1) Liu, X. H.; Tan, C. X.; Weng, J. Q. Phase transfer-catalyzed, one-pot synthesis of some novel N-pyrimidinyl-N'-nicotinyl thiourea derivatives, Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 552-557.
2. [2]
  (2) Liu, X. H.; Pan, L.; Ma, Y.; Weng, J. Q.; Tan, C. X.; Li, Y. H.; Shi, Y. X.; Li, B. J.; Li, Z. M.; Zhang, Y. G. Design, synthesis, biological activities, and 3D-QSAR of new N, N'-diacylhydrazines containing 2-(2, 4-dichlorophenoxy)propane moiety. Chem. Biol. Drug Des. 2011, 78, 689-694.
3. [3]
  (3) Sun, G. X.; Shi, Y. X.; Sun, Z. H.; Yang, M. Y.; Wu, H. K.; Weng, J. Q.; Tan, C. X.; Liu, X. H.; Li, B. J.; Zhang, Y. G. Synthesis and bioactivities of novel 1, 3, 4-oxadiazole derivatives containing pyridine moiety. Lett. Drug Des. Discov. 2014, 11, 1119-1123.
4. [4]
  (4) Sun, G. X.; Yang, M. Y.; Sun, Z. H.; Wu, H. K.; Liu, X. H.; Wei, Y. Y. Synthesis and bioactivities of novel 1, 3, 4-oxadiazole derivatives containing 1, 2, 3-thiadiazole moiety. Phosphorus Sulfur Silicon Relat. Elem. 2014, 189, 1895-1900.
5. [5]
  (5) Yan, S. L.; Yang, M. Y.; Sun, Z. H.; Min, L. J.; Tan, C. X.; Weng, J. Q.; Wu, H. K.; Liu, X. H. Synthesis and antifungal activity of 1, 2, 3-thiadiazole derivatives containing 1, 3, 4-thiadiazole moiety. Lett. Drug Des. Discov. 2014, 11, 940-943.
6. [6]
  (6) Liu, X. H.; Weng, J. Q.; Wang, B. L.; Li, Y. H.; Tan, C. X.; Li, Z. M. Microwave-assisted synthesis of novel fluorinated 1, 2, 4-triazole derivatives, and study of their biological activity. Res. Chem. Intermed. 2014, 40, 2605-2612.
7. [7]
  (7) Zhang, L. J.; Yang, M. Y.; Sun, Z. H.; Tan, C. X.; Weng, J. Q.; Wu, H. K.; Liu, X. H. Synthesis and antifungal activity of 1, 3, 4-thiadiazole derivatives containing pyridine group. Lett. Drug Des. Discov. 2014, 11, 1107-1111.
8. [8]
  (8) Min, L. J.; Tan, C. X.; Weng, J. Q.; Liu, X. H. Synthesis, crystal structure, and biological activity of a novel 1, 2, 3-thiadiazole compound containing 1, 2, 4-triazole moiety. Phosphorus Sulfur Silicon Relat. Elem. 2014, 189, 379-386.
9. [9]
  (9) Yang, M. Y.; Zhao, W.; Liu, X. H.; Tan, C. X.; Weng, J. Q. Synthesis, crystal structure and antifungal activity of 4-(5-((2, 4-dichlorobenzyl)thio)-4-phenyl-4H-1, 2, 4-triazol-3-yl)pyridine. Chin. J. Struct. Chem. 2015, 34, 203-207.
10. [10]
  (10) Liu, X. H.; Sun, Z. H.; Yang, M. Y.; Tan, C. X.; Weng, J. Q.; Zhang, Y. G.; Ma, Y. Microwave assistant one pot synthesis, crystal structure, antifungal activities and 3D-QSAR of novel 1, 2, 4-triazolo[4, 3-a]pyridines. Chem. Biol. Drug Des. 2014, 84, 342-347.
11. [11]
  (11) Liu, X. H.; Xu, X. Y.; Tan, C. X.; Weng, J. Q.; Xin, J. H.; Chen, J. Synthesis, crystal structure, herbicidal activities and 3D-QSAR study of some novel 1, 2, 4-triazolo[4, 3-a]pyridine derivatives. Pest Manag. Sci. 2015, 71, 292-301.
12. [12]
  (12) Cid, J. M.; Tresadern, G.; Vega, J. A.; de Lucas, A. I.; Matesanz, E.; Iturrino, L.; Linares, M. L.; Garcia, A.; Andres, J. I.; Macdonald, G. J. Discovery of 3-cyclopropylmethyl-7-(4-phenylpiperidin-1-yl)-8-trifluoromethyl[1, 2, 4]triazolo[4, 3-a]pyridine (JNJ-42153605): a positive allosteric modulator of the metabotropic glutamate 2 receptor. J. Med. Chem. 2012, 55, 8770-8789.
13. [13]
  (13) Yang, M. Y.; Zhai, Z. W.; Sun, Z. H.; Yu, S. J.; Liu, X. H.; Weng, J. Q.; Tan, C. X.; Zhao, W. G. A facile one-pot synthesis of novel 1, 2, 4-triazolo[4, 3-a]pyridine derivatives containing the trifluoromethyl moiety using microwave irradiation. J. Chem. Res. 2015, 39, 521-523.
14. [14]
  (14) Sadana, A. K.; Mirza, Y.; Aneja, K. R.; Prakash, O. Hypervalent iodine mediated synthesis of 1-aryl/hetryl-1, 2, 4-triazolo[4, 3-a] pyridines and 1-aryl/hetryl 5-methyl-1, 2, 4-triazolo[4, 3-a]quinolines as antibacterial agents. Eur. J. Med. Chem. 2003, 38, 533-536.
15. [15]
  (15) Kaplancikli, Z. A.; Altintop, M. D.; Ozdemir, A.; Turan-Zitouni, G.; Goger, G.; Demirci, F. Synthesis and in vitro evaluation of some hydrazone derivatives as potential antibacterial agents. Lett. Drug Des. Discov. 2014, 11, 355-362.
16. [16]
  (16) Altintop, M. D.; Ozdemir, A.; Ilgin, S.; Atli, O. Synthesis and biological evaluation of new pyrazole-based thiazolyl hydrazone derivatives as potential anticancer agents. Lett. Drug Des. Discov. 2014, 11, 833-839.
17. [17]
  (17) Li, W. Q.; Zhang, Z. J.; Nan, X.; Liu, Y. Q.; Hu, G. F.; Yu, H. T.; Zhao, X. B.; Wu, D.; Yan, L. T. Design, synthesis and bioactivity evaluation of novel benzophenone hydrazone derivatives. Pest Manag. Sci. 2014, 70, 667-673.
18. [18]
  (18) Wu, J.; Song, B. A.; Hu, D. Y.; Yue, M.; Yang, S. Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures. Pest Manag. Sci. 2012, 68, 801-810.
19. [19]
  (19) Filipovic, N.; Grubisic, S.; Jovanovic, M.; Dulovic, M.; Markovic, I.; Klisuric, O.; Marinkovic, A.; Mitic, D.; Andelkovic, K.; Todorovic, T. Palladium(II) complexes with N-heteroaromatic bidentate hydrazone ligands: the effect of the chelate ring size and lipophilicity on in vitro cytotoxic activity. Chem. Biol. Drug Des. 2014, 84, 333-341.
20. [20]
  (20) Zou, X. M.; Cheng, Y. H.; Ren, X. L.; Hu, F. Z.; Yang, H. Z. Synthesis of some new hydrazone compounds containing pyrazolyl nucleus. Chin. J. Org. Chem. 2005, 25, 554-557.
21. [21]
  (21) Zielinski, W.; Czardybon, W. Synthesis of 3, 5-diaryl-4-benzyledeneamino-1, 2, 4-triazoles and 4-amino-3, 5-diaryl-1, 2, 4-triazoles. Chem. Heterocycl. Compds. 2001, 37, 1107-1111.
22. [22]
  (22) Liu, X. H.; Tan, C. X.; Weng, J. Q. Synthesis, dimeric crystal, and fungicidal activity of1-(4-methylphenyl)-2-(5-((3, 5-dimethyl-
23. [23]
  1H-pyrazol-1-yl)methyl)-4-phenyl-4H-1, 2, 4-triazol-3-ylthio)ethanone. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 558-564.
24. [24]
  (23) Tong, J. Y.; Wu, H. K.; Sun, N. B.; Liu, X. H. Synthesis, crystal structure and biological activity of a new 1, 2, 4-triazole derivative, Chin. J. Struct. Chem. 2013, 32, 607-611.
25. [25]
  (24) Liu, X. H.; Zhai, Z.W.; Xu, X.Y.; Yang, M.Y.; Sun, Z.H.; Weng, J. Q.; Tan, C. X.; Chen, J. Facile and efficient synthesis and herbicidal activity determination of novel 1, 2, 4-triazolo[4, 3-a]pyridin-3(2H)-one derivatives via microwave irradiation. Bioorg. Med. Chem. Lett. 2015, 25, 5524-5528.
26. [26]
  (25) Weng, J. Q.; Wang, L.; Liu, X. H. Synthesis, crystal structure and herbicidal activity of a 1, 2, 4-triazol-5(4H)-one derivative. J. Chem. Soc. Pak. 2012, 34, 1248-1252.
27. [27]
  (26) Tan, C. X.; Shi, Y. X.; Weng, J. Q.; Liu, X. H.; Li, B. J.; Zhao, W. G. Synthesis and antifungal activity of 1, 2, 4-triazole derivatives containing cyclopropane moiety. Lett. Drug Des. Discov. 2012, 9, 431-435.
28. [28]
  (27) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.; Pittsburgh PA 2003, Gaussian 03, Revision B. 01.
29. [29]
  (28) Sheldrick, G. M. SHELXS97, Program for Crystal Structure Solution. University of Göttingen, Germany 1997.
30. [30]
  (29) Sheldrick, G. M. SHELXL97, Program for Crystal Structure Refinement. University of Göttingen, Germany 1997.
31. [31]
  (30) Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112-122.
32. [32]
  (31) Sun, G. X.; Yang, M. Y.; Shi, Y. X.; Sun, Z. H.; Liu, X. H.; Wu, H. K.; Li, B. J.; Zhang, Y. G. Microwave assistant synthesis, antifungal activity and DFT theoretical study of some novel 1, 2, 4-triazole derivatives containing pyridine moiety. Int. J. Mol. Sci. 2014, 15, 8075-8090.
33. [33]
  (32) Sun, N. B.; Fu, J. Q.; Weng, J. Q.; Jin, J. Z.; Tan, C. X.; Liu, X. H. Microwave assisted synthesis, antifungal activity and DFT theoretical study of some novel 1, 2, 4-triazole derivatives containing the 1, 2, 3-thiadiazole moiety. Molecules 2013, 18, 12725-12739.
34. [34]
  (33) Li, J. J.; Hua, X. W.; Fan, Z. J.; Ji, X. T.; Zong, G. N.; Li, F. Y.; Huang, Y.; Song, H. B.; Liu, C. L.; Morzherin, Y. Y. Synthesis, crystal structure and biological activity of diethyl 1, 4-dihydro-2, 6-dimethyl-4-(4-methyl-1, 2, 3-thiadiazol-5-yl)pyridine-3, 5-dicarboxylate. Chin. J. Struct. Chem. 2014, 33, 535-543.
35. [35]
  (34) Tan, C. X.; Weng, J. Q.; Liu, Z. X.; Liu, X. H.; Zhao, W. G. Synthesis, crystal structure and fungicidal activity of a novel 1, 2, 3-thiadiazole compound. Phosphorus Sulfur Silicon Relat. Elem. 2012, 187, 990-996.
36. [36]
  (35) Sun, Z. H.; Zhai, Z. W.; Yang, M. Y.; Liu, X. H.; Tan, C. X.; Weng, J. Q. Microwave assistant synthesis and dimeric crystal structure of 2-(((6-chloropyridin-3-yl)methyl)thio)-5-(pyridin-4-yl)-1, 3, 4-thiadiazole. Chin. J. Struct. Chem. 2014, 33, 1779-1783.
37. [37]
  (36) Liu, X. H.; Pan, L.; Tan, C. X.; Weng, J. Q.; Wang, B. L.; Li, Z. M. Synthesis, crystal structure, bioactivity and DFT calculation of new oxime ester derivatives containing cyclopropane moiety. Pestic. Biochem. Physiol. 2011, 101, 143-147.
38. [38]
  (37) Wang, Z. X.; Jian, F. F.; Duan, C. Y.; Bai, Z. P.; You, X. Z. 2-(2-Hydroxybenzylidene)-1-(2-picoloyl)hydrazine Hemihydrate. Acta Cryst. 1998, C54, 1927-1929.
39. [39]
  (38) Liu X. F.; Xiao X. W.; Liu X. H. Synthesis and crystal structure of the diiron azadithiolate complex [(mu-SCH₂)(2)NPh]Fe-2(CO)(5)(Ph2PCH2PPh2). Chin. J. Struct. Chem. 2011, 30, 1437-1441.
1. [1]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
2. [2]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
3. [3]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
4. [4]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
5. [5]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
6. [6]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
7. [7]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
8. [8]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
9. [9]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
10. [10]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
11. [11]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
12. [12]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
13. [13]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
14. [14]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
15. [15]
  Gang Lang , Jing Feng , Bo Feng , Junlan Hu , Zhiling Ran , Zhiting Zhou , Zhenju Jiang , Yunxiang He , Junling Guo . Supramolecular phenolic network-engineered C–CeO₂ nanofibers for simultaneous determination of isoniazid and hydrazine in biological fluids. Chinese Chemical Letters, 2024, 35(6): 109113-. doi: 10.1016/j.cclet.2023.109113
16. [16]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
17. [17]
  Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe₂Sn₄Bi₈]^3– and [Cr₂Sb₁₂]^3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048
18. [18]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
19. [19]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
20. [20]
  Zhengzheng LIU , Pengyun ZHANG , Chengri WANG , Shengli HUANG , Guoyu YANG . Synthesis, structure, and electrochemical properties of a sandwich-type {Co₆}-cluster-added germanotungstate. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1173-1179. doi: 10.11862/CJIC.20240039

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(847)
HTML views(36)

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