Citation: Yong-Lan FENG, Ying WANG, Wu-Jiu JIANG, Jiang-Xi YU, Fu-Xing ZHANG, Dai-Zhi KUANG. Synthesis, Structure and Fluorescence Properties of Bis(3-ethoxysalicylaldehyde) 1, 3-Benzyldiacyl Hydrazone Tetrabutyl(phenyl)ditin[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(1): 103-110. doi: 10.11862/CJIC.2022.026 shu

Synthesis, Structure and Fluorescence Properties of Bis(3-ethoxysalicylaldehyde) 1, 3-Benzyldiacyl Hydrazone Tetrabutyl(phenyl)ditin

  • Corresponding author: Dai-Zhi KUANG, hnkcq@qq.com
  • Received Date: 15 July 2021
    Revised Date: 21 October 2021

Figures(4)

  • The bis(3-ethoxysalicylaldehyde) 1, 3-benzyldiacyl hydrazone (H4L) ligand was prepared by the reaction of 3-ethoxysalicylaldehyde with benzene-1, 3-dicarbohydrazide in ethanol solution. Bis(3-ethoxysalicylaldehyde) 1, 3benzyldiacyl hydrazone tetrabutyl(phenyl)ditin, Bu4Sn2L (T1) and Ph4Sn2L (T2), were synthesized by solvothermal reaction of H4L with dibutyltin oxide and triphenyltin hydroxide in methanol, respectively. The structures of ligand and complexes were characterized by elemental analysis, IR, UV-Vis spectroscopy, NMR, and single-crystal X-ray diffraction. The molecular formula of H4L is C26H26N4O6. The crystal of H4L belongs to the monoclinic system and space group C2/c. Two formylhydrazide (3-ethoxy)salicylaldehydes are cis-symmetric configuration. The molecular formula of T1 is C42H58N4O6Sn2. The crystal of T1 belongs to the orthorhombic system and space group Pbcn. The two formylhydrazide (3-ethoxy)salicylaldehyde chains of H4L turn inward 180°, and a distorted trigonal bipyramid is formed by the coordination of coordinating atoms with tin. The molecular structure is axis-symmetric about C2…C4. The molecular formula of T2 is C50H42N4O6Sn2. The crystal of T2 belongs to the triclinic system, space group P1. One formylhydrazide (3-ethoxy)salicylaldehyde of H4L keeps the original configuration, and the other formylhydrazide (3-ethoxy)salicylaldehyde turns inward 180°. Two coordination chains with different configuration orientations were formed, which coordinated with diphenyltin to form a binuclear trans-asymmetric distorted trigonal bipyramid complexes. The fluorescence properties of trichloromethane solutions of H4L, T1, T2 (50 μmol·L-1) were tested. The results showed that H4L had weak fluorescence at 520 nm, and T1 and T2 had 14-15 times stronger fluorescence emission peaks than the ligand at 518 nm.
  • 加载中
    1. [1]

      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

    2. [2]

      Mazur L, Jarzembska K N, Kamiński R, Woźniak K, Pindelska E, Pisklak M Z. Substituent and Solvent Effects on Intermolecular Interactions in Crystals of N-Acylhydrazone Derivatives: Single-Crystal Xray, Solid-State NMR, and Computational Studies[J]. Cryst. Growth Des., 2014,14(5):2263-2281. doi: 10.1021/cg401866x

    3. [3]

      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

    4. [4]

      Hu J H, Li J B, Sun Y, Pei P X, Qi J. A Turn-on Fluorescent Chemosensor Based on Acylhydrazone for Sensing of Mg2+ with a Low Detection Limit[J]. RSC Adv., 2017,7(47):29697-29701. doi: 10.1039/C7RA04462C

    5. [5]

      Roztocki K, Szufla M, Hodorowicz M, Senkovska I, Kaskel S, Matoga D. Introducing a Longer versus Shorter Acylhydrazone Linker to a Metal-Organic Framework: Parallel Mechanochemical Approach, Nonisoreticular Structures, and Diverse Properties[J]. Cryst. Growth Des., 2019,19(12):7160-7169. doi: 10.1021/acs.cgd.9b01031

    6. [6]

      Pandian T S, Cho S J, Kang J. Dihydrogen Phosphate as a HydrogenBonding Donor Element: Anion Receptors Based on Acylhydrazone[J]. J.Org. Chem., 2013,78(23):12121-12127. doi: 10.1021/jo402103d

    7. [7]

      Feng Y L, Zhang F Xi, Kuang D Z. Syntheses, Structures and Herbicidal Activity of Bis(5-R-2-hydroxybenzylidene) Thiocarbohydrazide Monobutyltin Complexes[R: H(T1), Me(T2)][J]. Chin. J. Struct. Chem., 2019,38(5):719-726.  

    8. [8]

      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]. J. Am. Chem. Soc., 1992,114(22):8724-8725. doi: 10.1021/ja00048a069

    9. [9]

      He C, Wu X, Kong J C, Tao L T, Zhang X L, Duan C Y. A Hexanuclear Gadolinium - Organic Octahedron as a Sensitive MRI Contrast Agent for Selectively Imaging Glucosamine in Aqueous Media[J]. Chem.Commun., 2012,48:9290-9292. doi: 10.1039/c2cc33177b

    10. [10]

      FENG Y L, KUANG D Z, ZHANG F X, YU J X, JIANG W J, ZHU X M. Synthesis and Crystal Structure of Bis(4-(diethylamino)salicylaldehyde) Azodicarbonhydrazide Dibutyltin Complex with Aggregation Induced Emission Properties[J]. Chinese J. Inorg. Chem., 2019,35(2):307-313.  

    11. [11]

      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 

    12. [12]

      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.  

    13. [13]

      Yang L Y, Wu X, He C, Li Z Y, Duan C Y. Metal-Organic Polyhedra for Selective Sensing of Ribonucleosides Through the Cooperation of Hydrogen-Bonding Interactions[J]. Dalton Trans., 2010,39:7727-7732. doi: 10.1039/c0dt00002g

    14. [14]

      Liu Y, Lin Z H, He C, Zhao L, Duan C Y. A Symmetry-Controlled and Face - Driven Approach for the Assembly of Cerium - Based Molecular Polyhedral[J]. Dalton Trans., 2010,39:11122-11125. doi: 10.1039/c0dt01086c

    15. [15]

      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

    16. [16]

      Sheldrick G M. SHELXT—Integrated Space - Group and Crystal Structure Determination[J]. Acta Crystallogr. Sect. A, 2015,A71:3-8.  

    17. [17]

      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

    18. [18]

      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

    19. [19]

      HONG S H. Application of Spectral Analysis in Organic Chemistry. Beijing: Science Press, 1980: 368-385

    20. [20]

      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.  

    21. [21]

      Fakhraee S, Souri M. Double Hydrogen Bond Interaction in 7-Azaindole Complexes with Protic Solvents[J]. J. Mol. Graph. Model., 2016,70:45-53. doi: 10.1016/j.jmgm.2016.06.009

    22. [22]

      Dai J, Yamamoto M, Sowa T K, Maekawa M, Suenaga Y, Munakata M. Double Hydrogen Bond - and π - π - Stacking - Assembled Two Dimensional Copper(Ⅰ) Complex of 2 - Hydroxyquinoxaline[J]. Inorg.Chem., 1997,36(12):2688-2690. doi: 10.1021/ic961217q

    23. [23]

      Wang Z P, Xiang F F, Lu Y, Wei S, Li C, Liu X Q, Liu L C, Wang L. Double Hydrogen Bond Mediating Self-Assembly Structure of Cyanides on Metal Surface[J]. Physica B, 2016,499:70-75. doi: 10.1016/j.physb.2016.07.020

    24. [24]

      Feng L, Bai F Q, Wu Y, Zhang H X. Does the Molecular Structure of CaH2 Affect the Dihydrogen Bonding in CaH2…HY (Y=CH3, C2H3, C2H, CN, and NC) Complexes? A Quantum Chemistry Study Using MP2 and B3LYP Methods[J]. Sci. China Chem., 2012,55(2):262-269. doi: 10.1007/s11426-011-4391-y

  • 加载中
    1. [1]

      Xin MAYa SUNNa SUNQian KANGJiajia ZHANGRuitao ZHUXiaoli 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

    2. [2]

      Xinting XIONGZhiqiang XIONGPanlei XIAOXuliang NIEXiuying SONGXiuguang 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

    3. [3]

      Jingjing QINGFan HEZhihui LIUShuaipeng HOUYa LIUYifan JIANGMengting TANLifang HEFuxing ZHANGXiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003

    4. [4]

      Zhaoyang WANGChun YANGYaoyao SongNa HANXiaomeng LIUQinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114

    5. [5]

      Xiaoling LUOPintian ZOUXiaoyan WANGZheng LIUXiangfei KONGQun TANGSheng 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

    6. [6]

      Haitang WANGYanni LINGXiaqing MAYuxin CHENRui ZHANGKeyi WANGYing ZHANGWenmin WANG . Construction, crystal structures, and biological activities of two Ln3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188

    7. [7]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin 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

    8. [8]

      Kaimin WANGXiong GUNa DENGHongmei YUYanqin YEYulu 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

    9. [9]

      Peiran ZHAOYuqian LIUCheng HEChunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355

    10. [10]

      Yonghui ZHOURujun HUANGDongchao YAOAiwei ZHANGYuhang SUNZhujun CHENBaisong ZHUYouxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373

    11. [11]

      Yuanpei ZHANGJiahong WANGJinming HUANGZhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077

    12. [12]

      Qiuyang LUOXiaoning TANGShu XIAJunnan LIUXingfu YANGJie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110

    13. [13]

      Gaofeng WANGShuwen SUNYanfei ZHAOLixin MENGBohui 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

    14. [14]

      Youlin SIShuquan SUNJunsong YANGZijun BIEYan CHENLi LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061

    15. [15]

      Qilu DULi ZHAOPeng NIEBo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006

    16. [16]

      Huan ZHANGJijiang WANGGuang FANLong TANGErlin YUEChao BAIXiao WANGYuqi 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

    17. [17]

      Ruikui YANXiaoli CHENMiao CAIJing RENHuali CUIHua YANGJijiang 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

    18. [18]

      Xiaoxia WANGYa'nan GUOFeng SUChun HANLong 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

    19. [19]

      Lu LIUHuijie WANGHaitong WANGYing 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

    20. [20]

      Meirong HANXiaoyang WEISisi FENGYuting 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

Metrics
  • PDF Downloads(1)
  • Abstract views(746)
  • HTML views(119)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return