Citation: LU Yan, WU Siyu, MA Baiqing, SHI Jia, JIN Qifeng, YU Shijun. Synthesis and Properties of Polyesters Containing Schiff Base Side Groups and Their Zinc Complexes[J]. Chinese Journal of Applied Chemistry, ;2016, 33(4): 452-458. doi: 10.11944/j.issn.1000-0518.2016.04.150283 shu

Synthesis and Properties of Polyesters Containing Schiff Base Side Groups and Their Zinc Complexes

1.
School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China

Corresponding author: YU Shijun,
Received Date: 10 August 2015
Available Online: 9 December 2015
Fund Project:

Two kinds of novel polyesters containing Schiff base side groups(P5, P6) were synthesized by multistep reactions. Subsequently, P5 and P6 reacted with zinc acetate to get zinc complexes(P5-Zn, P6-Zn). The structures and properties of polyesters and zinc complexes were characterized by elemental analysis, FT-IR, UV-Vis, ¹H NMR, GPC, TG, DSC and fluorescence spectroscopy. Polyesters P5 and P6 are soluble in tetrahydrofurane(THF), CHCl₃, N,N-dimethyl formamide(DMF), N,N-dimethyl acetamide(DMAc), dimethylsulfoxide(DMSO), and N-methyl pyrrolidone(NMP). Complexes P5-Zn and P6-Zn can be partly dissolved in THF and CHCl₃, and completely dissolved in DMF, DMAc, DMSO, and NMP. The M_w and PDI of P5 and P6 are 4164, 6148 g/mol and 1.42, 1.43, respectively. The 5% mass loss temperatures of P5, P6, P5-Zn and P6-Zn are 339, 348, 367 and 358 ℃, respectively. The T_g values of P5, P5-Zn, P6 and P6-Zn are 88.8, 123.3, 39.8 and 63.8 ℃, respectively. Fluorescence emission peaks of P5 and P6 in DMF solution appear at 418 and 416 nm, emitting weak purple light. Fluorescence emission peaks of P5-Zn and P6-Zn in DMF solution appear at 505 and 506 nm, emitting strong green light. Fluorescence emission peaks of P5-Zn and P6-Zn in solid state appear at 527 and 532 nm, emitting strong green light.
- Schiff base,
- polyester,
- zinc complex,
- synthesis,
- property
1. [1]
  [1] Montazerozohori M,Musavi S A,Naghiha A,et al. Some New Nano-Structure Zinc(Ⅱ) Coordination Compounds of an Imidazolidine Schiff Base: Spectral, Thermal, Antimicrobial Properties and DNA Interaction[J]. Spectrochim Acta A Mol Biomol Spectrosc,2014,129(14):382-391.
2. [2]
  [2] Liu D F,Wu L Y,Feng W X,et al. Ring-Opening Copolymerization of CHO and MA Catalyzed by Mononuclear [Zn(L₂)(H₂O)] or Trinuclear [Zn₃(L₂)₂(OAc)₂] Complex Based on the Asymmetrical Bis-Schiff Base Ligand Precursor[J]. J Mol Catal A:Chem,2014,382(4):136-145.
3. [3]
  [3] Bastos M B R,Moreira J C,Farias P A M. Adsorptive Stripping Voltammetric Behaviour of UO₂(Ⅱ) Complexed with the Schiff Base N,N-Prime-Ehtyenebis(Salicylidenimine) in Aqueous 4-(2-Tydroxyethyl)-1-Piperazine Ethanesulfonic Acid Medium[J]. Anal Chim Acta,2000,408(1/2):83-88.
4. [4]
  [4] Ma H,Chen S H,et al. Studies on Electrochemical Behavior of Copper in Aerated NaBr Solutions with Schiff Bases[J]. J Electrochem Soc,2001,148(5):208-216.
5. [5]
  [5] Abdel A. Synthesis, Spectroscopic, Photoluminescence Properties and Biological Evaluation of Novel Zn(Ⅱ) and Al(Ⅲ) Complexes of NOON Tetradentate Schiff Bases[J]. Spectrochim Acta Part A,2012,97(11):388-396.
6. [6]
  [6] Erdemir S,Malkondu S. A Novel “Turn On” Fluorescent Sensor Based on Hydroxyl-Triphenylamine or Zn²⁺ and Cd ²⁺ Ions in MeCN[J]. Sens Actuators B,2013,188(11):1225-1229.
7. [7]
  [7] Borisov S M. Synthesis and Properties of New Phosphorescent Red Light-Excitable Platinum(Ⅱ) and Palladium(Ⅱ) Complexes with Schiff Bases for Oxygen Sensing and Triplet-Triplet Annihilation-Based Upconversion[J]. Inorg Chem,2013,52(3):1206-1216.
8. [8]
  [8] Caruso U,Barbara P,Antonio R,et al. Fluorescent Metallopolymers with Zn(Ⅱ) in a Schiff Base Phenoxide Coordination Environment[J]. Inorg Chem Commun,2013,29(3):138-140.
9. [9]
  [9] Selvi C,Nartop D. Novel Polymer Anchored Cr(Ⅲ) Schiff Base Complexes:Synthesis, Characterization and Antimicrobial Properties[J]. Spectrochim Acta Part A,2012,95(5):165-171.
10. [10]
  [10] Nishat N. Synthesis, Characterization, and Biological Evaluation of New Polyester Containing Schiff Base Metal Complexes[J]. J Therm Anal Calorim,2011,105(3):969-979.
11. [11]
  [11] Thomas G,Fox J,Paul J,et al. Flory, Second-Order Transition Temperatures and Related Properties of Polystyrene:I Influence of Molecular Weight[J]. J Appl Phys,1950,21(6):581-591.
12. [12]
  [12] HE Manjun. Polymer Physics[M]. Shanghai:Fudan University Press,1990,10(in Chinese).何曼君. 高分子物理[M]. 上海:复旦大学出版社,1990,10.
13. [13]
  [13] HOU Lixin,JIA Husheng,HAO Yuying,et al. Characterization and Photoluminescence Properties of an Azomethin-Zinc Complex[J]. Spectrosc Spectr Anal,2008,28(4):766-769(in Chinese).侯立信,贾虎生,郝育英,等. 希夫碱锌配合物的表征及光致发光性能[J]. 光谱学和光谱分析,2008,28(4):766-769.
14. [14]
  [14] ZHAO Guosheng,SHI Chuanxing,GUO Zhiqian,et al. Research Progress of Aggregation-Induced Emission[J]. Org Chem,2012,32:1620-1632(in Chinese).赵国生,史川兴,郭志前,等. 聚集诱导发光应用研究进展[J]. 有机化学,2012,32:1620-1632.
15. [15]
  [15] Andreas W,Friebe W,Manuela C,et al. Self-Assembly of P-Conjugated Bis(Terpyridine) Ligands with Zinc(Ⅱ) Ions:New Metallosupramolecular Materials for Optoelectronic Applications[J]. Polym Sci Part A:Polym Chem,2009,47(16):4083-4098.
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  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
3. [3]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
4. [4]
  Hong Zheng , Xin Peng , Chunwang Yi . The Tale of Caprolactam Cyclic Oligomers: The Ever-changing Life of “Princess Cyclo”. University Chemistry, 2024, 39(9): 40-47. doi: 10.12461/PKU.DXHX202403058
5. [5]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
6. [6]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
7. [7]
  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
8. [8]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
9. [9]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
10. [10]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
11. [11]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
12. [12]
  Qilu DU , Li ZHAO , Peng NIE , Bo 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
13. [13]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
14. [14]
  Keweiyang Zhang , Zihan Fan , Liyuan Xiao , Haitao Long , Jing Jing . Unveiling Crystal Field Theory: Preparation, Characterization, and Performance Assessment of Nickel Macrocyclic Complexes. University Chemistry, 2024, 39(5): 163-171. doi: 10.3866/PKU.DXHX202310084
15. [15]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
16. [16]
  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
17. [17]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming 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
18. [18]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
19. [19]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
20. [20]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(673)
HTML views(126)

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