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)

  • 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.
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    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

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