Citation: Yong-Lan FENG, Wu-Jiu JIANG, Fu-Xing ZHANG, Dai-Zhi KUANG. Solvothermal Synthesis, Structure, and Fluorescence Properties of Four Organotin Complexes Based on m-Phthaloyl Bis(substituted salicylaldehyde acylhydrazone)[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(6): 1171-1179. doi: 10.11862/CJIC.2022.105 shu

Solvothermal Synthesis, Structure, and Fluorescence Properties of Four Organotin Complexes Based on m-Phthaloyl Bis(substituted salicylaldehyde acylhydrazone)

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

Corresponding author: Dai-Zhi KUANG, hnkcq@qq.com
Received Date: 18 December 2021
Revised Date: 11 March 2022

Figures(2)

Four new organotin complexes based on m-phthaloyl bis(substituted salicylaldehyde acylhydrazone) (H₄L), (SnR²)₂L (1-4), were synthesized by solvothermal reaction of H₄L with R₃²SnOH, or one-pot solvothermal reaction of m-phthaloyl hydrazide, 3-tert-butyl salicylaldehyde, and tricyclohexyltin hydroxide, where H₄L=m-Ph (CONH—N=CH(o-OH)PhR¹)₂; R¹=NEt₂, R²=Ph (1); R¹=3, 5-di-tert-butyl=3, 5-t-2Bu, R²=Ph (2); R¹=3, 5-t-2Bu, R²=Cy (3); R¹=3-tert-butyl=3-t-Bu, R²=Cy (4). And they were characterized by elemental analysis, IR, and (¹H, ¹³C, and ¹¹⁹Sn) NMR. The structures of complexes 1-4 were confirmed by X-ray diffraction. Three"inward E-type"complexes 1-3 were formed by the inward orientation of two substituted salicylaldehyde acylhydrazone chains of H₄L and coordination with tin atoms. And two substituted salicylaldehyde acylhydrazone chains were oriented outward and coordinated with tin atoms to form an"outward E-type"complex 4. Complexes 1, 2, and 4 belong to the triclinic P1 space group and complex 3 belongs to the monoclinic P2₁/c space group. The central tin and the coordination atom form a five-coordinate distorted triangular bipyramids configuration. The fluorescence properties of the ligands and the complexes-chloroform solution showed that when free ligand m-Ph(CONH—N=CH(o-OH)PhNEt²)₂ (H₄L¹) with weak fluorescence and ligand m-Ph(CONH—N=CH(o-OH)Ph(3, 5-t-2Bu))₂ (H₄L²) without fluorescence coordinated with phenyltin or cyclohexyltin, the chloroform solution of the complexes emitted strong fluorescence.
- m-phthaloyl bis(substituted salicylaldehyde acylhydrazone),
- organotin complex,
- solvothermal synthesis,
- crystal structure,
- fluorescence properties
1. [1]
  Gao H, Li J Q, Kang P W, Chigan J Z, Wang H, Liu L, Xu Y S, Zhai L, Yang K W. N-acylhydrazones Confer Inhibitory Efficacy against New Delhi Metallo-β-Lactamase-1[J]. Bioorg. Chem., 2021,114:105138-105138. doi: 10.1016/j.bioorg.2021.105138
2. [2]
  Yao X D, Hu H M, Wang S B, Zhao W H, Song M X, Zhou Q G. Synthesis, Antimicrobial Activity, and Molecular Docking Studies of Aminoguanidine Derivatives Containing an Acylhydrazone Moiety[J]. Iran. J. Pharm. Res., 2021,2021(2):536-545.
3. [3]
  Wu S T, Liang X, Luo F, Liu H, Shen L Y, Yang X J, Huang Y, Xu H, Wu N, Zhang Q L, Redshaw C. Synthesis, Crystal Structure and Bioactivity of Phenazine-1-Carboxylic Acylhydrazone Derivatives[J]. Molecules, 2021,26(17):5320-5320. doi: 10.3390/molecules26175320
4. [4]
  Wanderson C S, Lucas D D, Jaqueline E Q, Hérika D A V, Vinícius B S, Andréia M L, Carlos H T P S, Giuliana M V V, Gilberto L B A. Synthesis and In Silico Studies of N-Acylhydrazone Derivatives as hnRNP K Ligands with Potential Anti-cancer Activity[J]. Curr. Bioact. Compd., 2020,16(4):432-441. doi: 10.2174/1573407215666190131121059
5. [5]
  Liu Y Y, Peng Q C, Li Y Y, Hou H W, Li K. A Simple Strategy for Constructing Acylhydrazone Photochromic System with Visible Color/Emission Change and Its Application in Photo-Patterning[J]. Chin. Chem. Lett., 2020,31(12):3271-3275. doi: 10.1016/j.cclet.2020.05.007
6. [6]
  Huang M L, Qiu R X, Pan Z H, Tian D, Tao Y W, Lin J Q, Luo G G. Thermally Triggered Isomerization in a Naphthalene-Based Acylhydrazone with Solid-State Optical Nonlinearity Response[J]. Eur. J. Inorg. Chem., 2020,2020(45):4313-4317. doi: 10.1002/ejic.202000767
7. [7]
  Yang Z Y, Wu D Q, Dai K, Cao S Q, Li Z C, Huang H Y, Shang Z B, Liang H, Yan M H, Xie S Y. A Facile Accessible Acylhydrazone as Al3+ Sensor with Excellent Sensitivity and Selectivity[J]. J. Mol. Struct., 2020,1201:1-8.
8. [8]
  Feng X S, Li X Z, Hu S J, Yan D N, Zhou L P, Sun Q F. Base- and Metal-Dependent Self-Assembly of Lathanide-Organic Coordination Polymers or Macrocycles with Tetradentate Acylhydrazone-Based Ditopic Ligands[J]. Chem. Asian J., 2021,16(11):1392-1397. doi: 10.1002/asia.202100256
9. [9]
  Popov L D, Levchenkov S I, Lukov V V, Gishko K B, Borodkin S A, Tupolova Y P, Askalepova O I, Vlasenko V G, Spiridonova D V, Lazarenko D A, Burlov A S, Shcherbakov I N. Acylhydrazone Based on 2-N-Tosylaminobenzaldehyde and Girard T Reagent: Synthesis, Structure, and Coordination Ability[J]. Russ. J. Gen. Chem., 2021,91(1):90-97. doi: 10.1134/S1070363221010102
10. [10]
  PU X H. Synthesis and Crystal Structure of Copper(Ⅱ) and Zinc(Ⅲ) Complexes with Schiff Base 2-((E)-(3-Chlorophenylimino)methyl)-6-bromo-4-chlorophenol[J]. Chinese J. Inorg. Chem., 2012,28(10):2211-2216.
11. [11]
  Luo W, Meng X G, Cheng G Z, Ji Z P. Synthesis, Characterization and Bioactivity of Two Novel Trinuclear Copper(Ⅱ)/Ni(Ⅱ) Complexes with Pentantate Ligand N-2-Methyl-acryl-salicylhydrazide[J]. Inorg. Chim. Acta, 2009,362:551-555. doi: 10.1016/j.ica.2008.05.007
12. [12]
  Gupta P, Panda T, Allu S, Borah S, Baishya A, Gunnam A, Nangia A, Naumov P, Nath N K. Crystalline Acylhydrazone Photoswitches with Multiple Mechanical Responses[J]. Cryst. Growth. Des., 2019,19(5):3039-3044. doi: 10.1021/acs.cgd.8b01860
13. [13]
  Chakraborty S, Bhattacharjee C R, Mondal P, Prasad S K, Rao D S S. Synthesis and Aggregation Behaviour of Luminescent Mesomorphic Zinc(Ⅱ) Complexes with'Salen'Type Asymmetric Schiff Base Ligands[J]. Dalton Trans., 2015,44(16):7477-7488. doi: 10.1039/C4DT03989K
14. [14]
  Maria P, Georgia K M, Maria V. Photo- and Acid-Degradable Polyacylhydrazone-Doxorubicin Conjugates[J]. Polymers, 2021,13(15)2461. doi: 10.3390/polym13152461
15. [15]
  Lin Z H, Emge T J, Warmuth R. Multicomponent Assembly of Cavitand-Based Polyacylhydrazone Nanocapsules[J]. Chem. Eur. J., 2011,17(34):9395-9405. doi: 10.1002/chem.201100527
16. [16]
  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 π-Acid Ligand[J]. J. Am. Chem. Soc., 1992,114(22):8724-8725. doi: 10.1021/ja00048a069
17. [17]
  Liu J J, Liu X R, Zhao S S, Yang Z W, Yang Z. Syntheses, Crystal Structures, Thermal Stabilities, CT-DNA, and BSA Binding Characteristics of a New Acylhydrazone and Its Co(Ⅱ), Cu(Ⅱ), and Zn(Ⅱ) Complexes[J]. J. Coord. Chem., 2020,73(7):1159-1176. doi: 10.1080/00958972.2020.1758316
18. [18]
  Dolomanov O V, Bourhis L J, Gildea R J, Howard J A K, Puschmann H. OLEX2: A Complete Structure Solution, Refinement and Analysis Program[J]. J. Appl. Cryst., 2009,42:339-341. doi: 10.1107/S0021889808042726
19. [19]
  Sheldrick G M. SHELXT-Integrated Space-Group and Crystal-Structure Determination[J]. Acta Crystallogr. Sect. A, 2015,A71:3-8.
20. [20]
  Wu L M, Li Q, Jin L F, Zhou Z Q.. Synthesis and Structure of the Acylhydrazone Schiff Base[J]. Chin. J. Struct. Chem., 2010,29(9):1399-1403.
21. [21]
  Lin H W. Synthesis and Crystal Structure of Isonicotinic Acid[1-(3, 5- Dibromo-2-hydroxyphenyl)methylidene]hydrazide Methanol[J]. Chin. J. Struct. Chem., 2007,26(7):773-776.
22. [22]
  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/Mesalicylaldehyde) Carbohydrazide: Syntheses, Structures, Fluorescent Properties and Herbicidal Activity[J]. Chin. J. Struct. Chem., 2020,39(4):682-692.
23. [23]
  Nath M, Saini P K. Chemistry and Applications of Organotin(Ⅳ) Complexes of Schiff Bases[J]. Dalton Trans., 2011,40:7077-7121. doi: 10.1039/c0dt01426e
24. [24]
  Yan F F, Ma C L, Li Q L, Zhang S L, Ru J, Cheng S, Zhang R F. Syntheses, Structures and Anti-tumor Activity of Four Organotin(Ⅳ) Dicarboxylates Based on (1, 3, 4-Thiadiazole-2, 5-diyldithio) Diacetic Acid[J]. New J. Chem., 2018,42:11601-11609. doi: 10.1039/C8NJ00431E
25. [25]
  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[J]. Chin. J. Struct. Chem., 2020,39(4):673-681.
26. [26]
  FENG Y L, YANG C L, ZHANG F X, KUANG D Z. Synthesis, Characterization, Fluorescence Properties and Herbicidal Activity of Bis (substituted salicylaldehyde) Carbohydrazide and Its Benzyltin Complexes[J]. Chinese J. Inorg. Chem., 2019,35(10):1737-1745. doi: 10.11862/CJIC.2019.205
1. [1]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
2. [2]
  Lifang HE , Yaoze LUO , Qiying SHI , Jianxin TANG , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and properties of hydrated tricyclohexyltin theophylline-7-acetic acid complex. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 632-640. doi: 10.11862/CJIC.20250244
3. [3]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
4. [4]
  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
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]
  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
7. [7]
  Zihe SONG , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Crystal structure, thermal analysis, and luminescence properties of six heterocyclic lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 181-192. doi: 10.11862/CJIC.20250126
8. [8]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
9. [9]
  Wenya DING , Fangfei XU , Jiayu GU , Xinran CHEN , Kai CHEN . Synthesis and crystal structure of three cucurbit[6]uril-cadmium supramolecular assemblies. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 808-816. doi: 10.11862/CJIC.20260012
10. [10]
  Jiarong ZHU , Xiaohua ZHANG , Xinting XIONG , Xuliang NIE , Xiuying SONG , Miaomiao ZHANG , Dayong PENG , Xiuguang YI . Crystal structure, Hirshfeld surface analysis, and antifungal activity of five complexes based on 2,5-bis(carboxymethoxy)terephthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2358-2370. doi: 10.11862/CJIC.20250150
11. [11]
  Zhihui ZONG , Zijie ZHAO , Lei HUANG , Zhicheng PAN , Shan WANG , Lili LIANG , Huaqing LIU , Enli ZHANG . Synthesis, crystal structures, and antitumor activity of two metal complexes of imidazolyl acylhydrazones. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 1048-1062. doi: 10.11862/CJIC.20250330
12. [12]
  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
13. [13]
  Yinxia SUN , Liping LIU , Xue BAI , Yu SUN , Wanhong SUN , Zhepeng DENG , Jianghai CHEN , Jianjun WANG , Li XU , Shuzhen ZHANG . Synthesis and crystal structures of Co(Ⅱ)/Cu(Ⅱ) coordination polymers based on solvent and ligand concentration regulation strategy. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 340-354. doi: 10.11862/CJIC.20250226
14. [14]
  Ran ZHUANG , Xinru WANG , Ruwei SHEN , Dunru ZHU . Syntheses, crystal structures and Hirshfeld surface analyses of three 3-pyridazinyl-substituted triaryltriazoles and their Cu(Ⅱ) complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(8): 1712-1722. doi: 10.11862/CJIC.20260136
15. [15]
  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
16. [16]
  Fan LIU , Xiaoli CHEN , Jing REN , Yantao LEI , Huali CUI , Hua YANG , Jijiang WANG . Highly sensitive and multi-response Zn-MOF fluorescence sensor: Design, synthesis, and detection of 4-nitrophenol, Cu²⁺, and pyrimethanil. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 872-882. doi: 10.11862/CJIC.20250287
17. [17]
  Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy₄-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
18. [18]
  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
19. [19]
  Jiaojiao CHEN , Gaiyan GUO , Hua YANG , Shuo LIU , Lulu DONG , Xiaoli CHEN , Huali CUI , Jijiang WANG . Syntheses, structures, fluorescence properties, and applications of two Cd-based metal-organic framework materials based on polycarboxylic acids. Chinese Journal of Inorganic Chemistry, 2026, 42(8): 1763-1778. doi: 10.11862/CJIC.20250359
20. [20]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(4997)
HTML views(184)

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