Citation: Yong-Lan FENG, Wu-Jiu JIANG, Fu-Xing ZHANG, Dai-Zhi KUANG. Synthesis, Structural Characterization, Fluorescence Properties and Herbicidal Activity of Bis(substituted salicylaldehyde) Carbohydrazide Dibutyltin Complexes[J]. Chinese Journal of Structural Chemistry, ;2021, 40(12): 1639-1646. doi: 10.14102/j.cnki.0254-5861.2011-3214 shu

Synthesis, Structural Characterization, Fluorescence Properties and Herbicidal Activity of Bis(substituted salicylaldehyde) Carbohydrazide Dibutyltin Complexes

Key Laboratory of Functional Metal-organic Compounds of Hunan Province, Key Laboratory of Functional Organometallic Materials of College of Hunan Province, Department of Chemistry and Material Science, Hengyang Normal University, Hengyang, Hunan 421008, China

Corresponding author: Dai-Zhi KUANG, hnkcq@qq.com
Received Date: 10 April 2021
Accepted Date: 19 August 2021

Fund Project: the Innovation Platform Open Foundation for Colleges and Universities of Hunan Province 16k011

Figures(2)

A series of dibutyltin complexes, (Bu₂Sn)₂L, [(Bu₂Sn)₂L]₃ and H₂LSnBu₂, were synthesized by microwave-assisted methanolic solvothermal method, where H₄L is [2-(OH)-R-ArCH=NNH]₂CX, and X = O, R = 4-NEt₂ (T1), 5-Br (T2); X = S, R = H (T3); R = 5-Br (T4). Their structures were characterized by elemental analysis, IR and (¹H, ¹³C)-NMR spectra. The molecular structure of T2 was confirmed by X-ray diffraction. The crystal of T2 belongs to monoclinic system, space group Ia. Five-coordinated distorted triangular bipyramids and six-coordinated distorted octahedral configurations were formed by the coordination of oxygen and nitrogen atoms of ligand with two dibutyltins, thus forming a trimeric hexanuclear butyltin complex by the cross coordination of three units (Bu₂Sn)₂L with enol imines. The T2 and T4 exhibit fluorescence emission in DMF solvents and DMF-water mixture. The fluorescence intensity of T2-DMF-H₂O system decreases almost linearly with the increase of water volume fraction (WVF). The aggregation fluorescence enhancement effect of T4-DMF-H₂O solution system increases with the increase of WVF at the range of 0~20% WVF. When WVF is more than 20%, the fluorescence intensity decreases with the increase of WVF. In addition, T1~T4 have broad growth activities on target plants, such as Portulaca oleracea L., Amaranthus spinosus L., Cassia tora L., Brassica campestris L.ssp.chinensis var.utilis Tsen et Lee, and Amaranthus tricolor L., and can be used as a candidate herbicide for further research.
- bis(substituted salicylaldehyde) carbohydrazide dibutyltin,
- fluorescence properties,
- herbicidal activity
1. [1]
  Mandal, S. K.; Que, L. Models for amide ligation in nonheme iron enzymes. Inorg. Chem. 1997, 36, 5424–5425. doi: 10.1021/ic970541y
2. [2]
  Terrence, J. C.; Brian, G. F.; Zheng, G. H.; Kimberly, L. K.; Eckard, M.; Clifford, E. F. R.; Wright, L. J. High valent transition metal chemistry. Synthesis and characterization of an intermediate-spin iron(Ⅳ) complex of a strong pi-acid ligand. J. Am. Chem. Soc. 1992, 114, 724–8725.
3. [3]
  Wu, W. S.; Dai, J. C.; Zheng, Y. Y.; Huang, T. T.; Lan, X. R.; Lin, Y. X. Crystal structure and fluorescence character of palladium(Ⅱ) complex containing salicylidene thiosemicarbazone. Acta Chim. Sinica 2004, 62, 1801–1806.
4. [4]
  Sun, G. C.; Qu, J. Q.; Wang, L. F.; Chen, N. S.; Li, Y.; Chen, X. G.; Xie, J. X. Synthesis, characterization and biological activites of transition metal complexes with Schiff base ligand 4-[indol-3-yl]-but-3-en-2-one benzoyl hydrazone. Chin. J. Inorg. Chem. 2005, 21, 1069–1072.
5. [5]
  Yu, C. J.; Jiao, L. J.; Zhang, P.; Feng, Z. Y.; Cheng, C.; Wei, Y.; Mu, X. L.; Hao, E. H. Highly fluorescent BF₂ complexes of hydeazine-Schiff base linked bispyrrole. Org. Lett. 2014, 16, 3048–3051. doi: 10.1021/ol501162f
6. [6]
  Sutradhar, M.; Barman, T. R.; Rentschle, E. Coordination versatility of 1, 5-bis(salicylidene)carbohydrazide in Ni(Ⅱ) complexes. Inorg. Chem. Commun. 2014, 39, 140–143. doi: 10.1016/j.inoche.2013.11.018
7. [7]
  Zhu, J. H.; Zheng, X. D.; Guo, G. Z.; Zhang, Y. Q.; Wu, B. W. Microwave-assisted synthesis of asymmetrical 1, 5-disubstituted carbonohydrazide and crystal structure. Chin. J. Org. Chem. 2015, 35, 1975–1980. doi: 10.6023/cjoc201503004
8. [8]
  Feng, Y. L.; Zhang, F. X.; Yu, J. X.; Jiang, W. J.; Kuang, D. Z. Syntheses, structures, spectroscopic properties and herbicidal activity of 1-(2-hydroxybenzylidene)-5-(4-hydroxy-3-methoxybenzylidene) carbohydrazide butyltin complexes. Chin. J. Inorg. Chem. 2018, 34, 1857–1863.
9. [9]
  Mirta, R.; Nives, G.; Ivan, H.; Tomislav, J.; Nenad, J.; Janez, P.; Primoz, S.; Predrag, N. Multiple solid forms of 1, 5-bis(salicylidene)carbohydrazide: polymorph-modulated thermal reactivity. Cryst. Growth Des. 2014, 14, 2900–2912. doi: 10.1021/cg500203k
10. [10]
  Feng, Y. L.; Zhang, F. X.; Kuang, D. Z.; Yang, C. L. Two novel dibutyltin complexes with trimers and hexanuclear based on the bis(5-Cl/Me-salicylaldehyde) carbohydrazide: syntheses, structures, fluorescent properties and herbicidal activity. Chin. J. Struct. Chem. 2020, 39, 682–692.
11. [11]
  Yang, C. L.; Feng, Y. L.; Zhang, F. X.; Yu, J. X.; Jiang, W. J.; Kuang, D. Z. Syntheses, structure and herbicidal activity of bis(substituted salicylaldehyde) carbohydrazide n-butyltin complexes. Chin. J. Appl. Chem. 2018, 35, 795–801.
12. [12]
  Feng, Y. L.; Zhang, F. X.; Kuang, D. Z. Syntheses, structures and herbicidal activity of bis(5-R-2-hydroxybenzylidene) thiocarbohydrazide monobutyltin complexes [R: H(T1), Me(T2)]. Chin. J. Struct. Chem. 2019, 38, 719–726.
13. [13]
  Fang, X. N.; Xiao, Y. A.; Sui, Y.; Hu, R. H.; Chen, H. M. Synthesis, crystal structure and antimicrobial activities of dibutyltin(IV) complex of 1, 5-bis(5-bromo-2-hydroxybenzylidene)thiocarbohydrazide. J. Jinggangshan University 2017, 28, 14–18
14. [14]
  Sheldrick, G. M. SHELXL-2014/7, University of Göttingen, Germany 2014.
15. [15]
  Jiang, W. J.; Tan, Y. X.; Kuang, D. Z.; Zhang, F. X.; Liu, M. Q. Microwave-assisted self-assembly synthesis of organotin complexes and biological activities. Sci. China-Chem. 2019, 49, 1083–093.
16. [16]
  Yang, C. L.; Feng, Y. L.; Zhang, F. X.; Yu, J. X.; Jiang, W. J.; Kuang, D. Z.; Yang, N. F. Microwave-solvent thermal syntheses, crystal struture and herbicidal activity of bis(3, 5-di-t-butylsalicylaldehyde) carbohydrazide dibutyltin complexes. Chin. J. Inorg. Chem. 2017, 33, 1397–1402.
17. [17]
  Salam, M. A.; Affan, M. A.; Ahmad, F. B.; Arafath, M. D. A.; Tahir, M. I. M.; Shamsuddin, M. B. Synthesis, characteriztion, antibacterial, and cytotoxic activities of organotin(Ⅳ) complexes derived from N(4)-cyclohexylthiosemicarbazone: X-ray crystal structure of [Ph₂SnCl(L)]. J. Coord. Chem. 2012, 65, 3174–3187. doi: 10.1080/00958972.2012.711823
18. [18]
  Mendes, I. C.; Moreira, J. P.; Speziali, N. L.; Mangrich, A. S.; Takahashi, J. A.; Beraldo, H. N(4)-tolyl-2-benzoylpyridine thiosemicarbazones and their copper(II) complexes with significant antifungal activity. Crystal structure of N(4)-para-tolyl-2-benzoylpyridine thiosemicarbazone. J. Braz. Chem. Soc. 2006, 17, 1571–1577.
19. [19]
  Jiang, W. J.; Mo, T. Z.; Zhang, F. X.; Kuang, D. Z.; Tan, Y. X. Syntheses, crystal structures and in vitro anticancer activities of dibenzyltin compounds based on the N-(2-phenylacetic acid)-aroyl hydrazone. Chin. J. Struct. Chem. 2020, 39, 673–681.
20. [20]
  Luo, J. D.; Xie, Z. L.; Lam, J. W. Y.; Cheng, L.; Chen, H. Y.; Qiu, C. F.; Kwok, H. S.; Zhan, X. W.; Liu, Y. Q.; Zhu, D. B.; Tang, B. Z. Aggregation-induced emission of 1-methyl-1, 2, 3, 4, 5-pentaphenylsilole. Chem. Commun. 2001, 1740–1741.
21. [21]
  Tang, W. X.; Xiang, Y.; Tong, A. J. Salicylaldehyde azines as fluorophores of aggregation-induced emission enhancement characteristics. J. Org. Chem. 2009, 74, 2163–2166.
22. [22]
  Feng, Y. L.; Kuang, D. Z.; Zhang, F. X.; Yu, J. X.; Jiang, W. J.; Zhu, X. M. Syntheses and crystal structures of bis(4-(diethylamino)salicylaldehyde) azodicarbonhydrazide dibutyltin complex with aggregation induced emission properties. Chin. J. Inorg. Chem. 2019, 35, 307–313.
1. [1]
  Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368
2. [2]
  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
3. [3]
  Yanbing Shen , Yuan Yuan , Yaxin Wang , Xiaonan Ma , Wensheng Yang , Yulan Chen . Dihydroanthracene bridged bis-naphthopyrans: A multimodal chromophore with mechano- and photo-chromic properties. Chinese Chemical Letters, 2024, 35(5): 108949-. doi: 10.1016/j.cclet.2023.108949
4. [4]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
5. [5]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
6. [6]
  Shengwen Guan , Zhaotong Wei , Ningxu Han , Yude Wei , Bin Xu , Ming Wang , Junjuan Shi . Construction of metallo-complexes with 2,2′:6′,2″-terpyridine substituted triphenylamine in different modified positions and their photophysical properties. Chinese Chemical Letters, 2024, 35(7): 109348-. doi: 10.1016/j.cclet.2023.109348
7. [7]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
8. [8]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
9. [9]
  Deshuai Zhen , Chunlin Liu , Qiuhui Deng , Shaoqi Zhang , Ningman Yuan , Le Li , Yu Liu . A review of covalent organic frameworks for metal ion fluorescence sensing. Chinese Chemical Letters, 2024, 35(8): 109249-. doi: 10.1016/j.cclet.2023.109249
10. [10]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
11. [11]
  Ying Xu , Chengying Shen , Hailong Yuan , Wei Wu . Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting. Chinese Chemical Letters, 2024, 35(9): 109324-. doi: 10.1016/j.cclet.2023.109324
12. [12]
  Yuxin Li , Chengbin Liu , Qiuju Li , Shun Mao . Fluorescence analysis of antibiotics and antibiotic-resistance genes in the environment: A mini review. Chinese Chemical Letters, 2024, 35(10): 109541-. doi: 10.1016/j.cclet.2024.109541
13. [13]
  Zhihao Gu , Jiabo Le , Hehe Wei , Zehui Sun , Mahmoud Elsayed Hafez , Wei Ma . Unveiling the intrinsic properties of single NiZnFeO_x entity for promoting electrocatalytic oxygen evolution. Chinese Chemical Letters, 2024, 35(4): 108849-. doi: 10.1016/j.cclet.2023.108849
14. [14]
  Wenzhong Zhang , Zirui Yan , Lingcheng Chen , Yi Xiao . Sn-fused perylene diimides: Synthesis, mechanism, and properties. Chinese Chemical Letters, 2024, 35(10): 109582-. doi: 10.1016/j.cclet.2024.109582
15. [15]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
16. [16]
  Xinyi Hu , Riguang Zhang , Zhao Jiang . Depositing the PtNi nanoparticles on niobium oxide to enhance the activity and CO-tolerance for alkaline methanol electrooxidation. Chinese Journal of Structural Chemistry, 2023, 42(11): 100157-100157. doi: 10.1016/j.cjsc.2023.100157
17. [17]
  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
18. [18]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
19. [19]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
20. [20]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(159)
HTML views(1)

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