2,5-二羟基苯甲醛缩肼席夫碱的性质和研究
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摘要
设计和合成了一种双席夫碱。利用红外光谱对其结构进行表征,研究了其在不同溶剂中的紫外吸收光谱和荧光光谱,探究了过渡金属离子对紫外和荧光光谱的影响及聚集诱导发光(AIE)性质。结果表明,在不同溶剂中化合物的紫外光谱发生蓝移,荧光发射强度随溶剂极性增加强度减弱,且发生红移。通过紫外光谱和荧光光谱说明Fe~(3+)、Cu~(2+)在溶液中和化合物分子发生较强的相互作用,生成稳定配合物。同时该化合物没有表现出明显的AIE性质。
A double Schiff base was designed and synthesized. Its structure was characterized by infrared spectroscopy. UV-Vis absorption and fluorescence spectra of the target compound in different solvents as well as the effect of transition metal ions were studied. The aggregation-induced emission(AIE) was also investigated. The results show a weak blue shift was observed from UV-Vis spectrum in different solvents and the fluorescence emission intensity weakened with the increase of solvent polarity. Fe~(3+) and Cu~(2+) have strong effects on the target compound because of the coordination between metal ions and target compound. The compound have not obvious AIE properties.
A double Schiff base was designed and synthesized. Its structure was characterized by infrared spectroscopy. UV-Vis absorption and fluorescence spectra of the target compound in different solvents as well as the effect of transition metal ions were studied. The aggregation-induced emission(AIE) was also investigated. The results show a weak blue shift was observed from UV-Vis spectrum in different solvents and the fluorescence emission intensity weakened with the increase of solvent polarity. Fe~(3+) and Cu~(2+) have strong effects on the target compound because of the coordination between metal ions and target compound. The compound have not obvious AIE properties.
引文
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[15] Meng F D,Zhao Q Q,Li M X,et al.Synthesis and Characterization of Ag(Ⅰ)-amino Acid Schiff Base Complexes and Inhibition to Tobaccum Mosaic Virus [J].Chem Reagents,2000(3):176-177 (in Chinese).(孟凡德,赵全芹,李明霞,等.银-氨基酸席夫碱配合物的合成、表征及对烟草花叶病毒抑制作用初探[J].化学试剂,2000(3):176-177.)
[16] Yao K M,Zhou W,Lu G,et al.A New Asymmetric Schiff Base Complex with Rare Earth Complex Mechanism and Spectrum [J].Sci Chian Ser B,1999(3):259-263 (in Chinese).(姚克敏,周文,鲁桂,等.一种新的不对称Schiff碱与稀土配合物合成机理及波谱[J].中国科学(B辑),1999(3):259-263.)
[17] Yao K M,Li D C,Shen L F,et al.Synthesis and Characterization of New Lanthanide Complexes with N-(2,4-Dihydroxybenzalidene)-anthranilic Acid and Their Catalytic Activity [J].Acta Chim Sin,1993(7):677-682 (in Chinese).(姚克敏,李冬成,沈联芳,等.镧系与邻氨基苯甲酸型Schiff碱配合物的合成、表征及催化活性[J].化学学报,1993(7):677-682.)
[18] Goo C.Based on the Structure of Schiff’s Base Al3+ Preparation and Its Performance Study of Fluorescent Probe [D].Jinan:Qilu University of Technology,2016 (in Chinese).(高超.基于席夫碱结构的Al3+荧光探针的制备及其性能研究[D].济南:齐鲁工业大学,2016.)
[19] Ding G H,Zhang X S,Fan R M.Synthesis and Fluorescence Performance of Transition Metal Complexes with Chiff Base [J].Chin J Synth Chem,2010,18(2):259-261 (in Chinese).(丁国华,张晓松,樊润梅.席夫碱过渡金属配合物的合成及其荧光性能[J].合成化学,2010,18(2):259-261.)
[20] Gong C X,Wei X P,Li J P.Fabrication and Application in SCN- Detection of Copper(Ⅱ) Ionic Selective Electrode Based on Salicylaldehyde-1,2-phenylenediamine Sensitive Membrane [J].Chin J Appl Chem,2010,27(8):950-954 (in Chinese).(巩春侠,魏小平,李建平.水杨醛缩邻苯二胺双席夫碱敏感膜Cu(Ⅱ)离子选择性电极及SCN-的测定[J].应用化学,2010,27(8):950-954.)
[21] Yang L L.Synthesis of New Carbazolebased Schiff Base Derivatives and Their Ion Recognition Properties [D].Hefei:Anhui University,2013 (in Chinese).(杨莲莲.新型咔唑基席夫碱衍生物的合成及离子识别性能研究[D].合肥:安徽大学,2013.)
[22] Wang G Q.Heterocyclic Schiff Bases as Al3+,Mg2+,Cu2+,Zn2+ Ion Probe Synthesis and Properties Study [D].Lanzhou:Lanzhou University,2016 (in Chinese).(王冠群.杂环类席夫碱作为Al3+,Mg2+,Cu2+,Zn2+离子探针的合成及其性质研究[D].兰州:兰州大学,2016.)
[23] Hou P G,Lu C H.Progress in the Application of Infrared Spectroscopy in the Identification of Pharmaceutical Preparations [J].Chin J Hosp Pharm,2013,33(8):648-649 (in Chinese).(侯鹏高,吕长淮.红外光谱法在药物制剂鉴别中的应用研究进展[J].中国医院药学杂志,2013,33(8):648-649.)
[2] Yan F.A Schiff Base Cobalt Compound,Its Preparation Method and Preparation Method of Polycarbonate [J].China Rubber/Plast Technol Equip,2016,42(22):77 (in Chinese).(燕丰.一种席夫碱钴化合物、其制备方法及聚碳酸酯的制备方法[J].橡塑技术与装备,2016,42(22):77.)
[3] Zheng Y,Ma K,Li H,et al.One Pot Synthesis of Imines from Aromatic Nitro Compounds with a Novel Ni/SiO2 Magnetic Catalyst [J].Catal Lett,2009,128(3-4):465-474.
[4] Tian G,Xu W Y,Che Q,et al.Investigation of Organic Photochromic Salicylaldehyde Schiff Bases [J].Mod Chem Ind,2007(S1):253-256 (in Chinese).(田刚,许文苑,车强,等.水杨醛类席夫碱有机光致变色化合物的研究[J].现代化工,2007(S1):253-256.)
[5] Jones R D,Sununervile D A,Basolo E.Synthetic Oxygen Carriers Related to Biological Systems[J].Chem Rev,1979,79(2):139-179.
[6] Rybak-Aklmova E V,Otto W,Deardorf P,et al.Kinetics and Equilibria of Dioxygen Binding to a Vacant Site in Cobalt(Ⅱ) Complexes with Pentadentate Ligands[J].Inorg Chem,1997,36(13):2 746-2 753.
[7] Wu Y M,Qi S H,Wang D H,et al.Advance in Conductive Schiff Bases [J].Chem Ind Eng,2008,25(1):82-86 (in Chinese).(吴有明,齐署华,王东红,等.席夫碱导电性研究[J].化学工业与工程,2008,25(1):82-86.)
[8] Nikoorazm M,Ghorbani F,Ghorbani-Choghamarani A,et al.Synthesis and Characterization of a Pd(0) Schiff Base Complex Anchored on Magnetic Nanoporous MCM-41 as a Novel and Recyclable Catalyst for the Suzuki and Heck Reactions Under Green Conditions [J].Chin J Catal,2017,38(8):1 413-1 422.
[9] Li L Z,Shang X M,Du H Z,et al.Synthesis and Structure of Dimeric Schiff Base Aluminum Complex and Its Catalysis on Ring-opening Polymerization of ε-Caprolactone [J].Chin J Appl Chem,2007(8):878-882 (in Chinese).(李良钊,尚晓敏,杜鸿志,等.席夫碱铝双核配合物的合成及其对ε-己内酯的催化作用[J].应用化学,2007(8):878-882.)
[10] Fan J F,Tian L F.Inhibition Performance of Schiff Base for 20# Carbon Steel in Hydrochloric Acidic Solution [J].Corros Prot,2007(4):198-201 (in Chinese).(范建凤,田丽芳.席夫碱对20#碳钢在盐酸介质中的缓蚀作用[J].腐蚀与防护,2007(4):198-201.)
[11] Shi J.Studies on the Synthesis and Corrosion Inhibition Properties of Several Schiff Bases [D].Dalian:Liaoning Normal University,2016 (in Chinese).(石晶.席夫碱的合成与缓蚀性能研究[D].大连:辽宁师范大学,2016.)
[12] Zhai G J,Zhai G Z.Studies on Cu(Ⅱ) Chelates with 3,5-Dibromosalicylaldehyde Schiff Base [J].Shandong Chem Ind,2002(1):11-12 (in Chinese).(翟冠杰,翟冠中.3,5-二溴水杨醛亚胺合Cu(Ⅱ)配合物研究[J].山东化工,2002(1):11-12.)
[13] You J,Wang X,Liu P,et al.Solvent-free Synthesis and Characterization of L-Amino Acid Schiff Bases [J].Chin J Org Chem,2011,31(6):832-835 (in Chinese).(由君,王鑫,刘波,等.L-氨基酸席夫碱的无溶剂法合成及其结构表征[J].有机化学,2011,31(6):832-835.)
[14] Wang X.Synthesis and Characterization of L-Amino Acid Schiff Base and Complexes [D].Harbin:Harbin University of Science and Technology,2011 (in Chinese).(王鑫.L-氨基酸席夫碱及其配合物的合成及结构表征[D].哈尔滨:哈尔滨理工大学,2011.)
[15] Meng F D,Zhao Q Q,Li M X,et al.Synthesis and Characterization of Ag(Ⅰ)-amino Acid Schiff Base Complexes and Inhibition to Tobaccum Mosaic Virus [J].Chem Reagents,2000(3):176-177 (in Chinese).(孟凡德,赵全芹,李明霞,等.银-氨基酸席夫碱配合物的合成、表征及对烟草花叶病毒抑制作用初探[J].化学试剂,2000(3):176-177.)
[16] Yao K M,Zhou W,Lu G,et al.A New Asymmetric Schiff Base Complex with Rare Earth Complex Mechanism and Spectrum [J].Sci Chian Ser B,1999(3):259-263 (in Chinese).(姚克敏,周文,鲁桂,等.一种新的不对称Schiff碱与稀土配合物合成机理及波谱[J].中国科学(B辑),1999(3):259-263.)
[17] Yao K M,Li D C,Shen L F,et al.Synthesis and Characterization of New Lanthanide Complexes with N-(2,4-Dihydroxybenzalidene)-anthranilic Acid and Their Catalytic Activity [J].Acta Chim Sin,1993(7):677-682 (in Chinese).(姚克敏,李冬成,沈联芳,等.镧系与邻氨基苯甲酸型Schiff碱配合物的合成、表征及催化活性[J].化学学报,1993(7):677-682.)
[18] Goo C.Based on the Structure of Schiff’s Base Al3+ Preparation and Its Performance Study of Fluorescent Probe [D].Jinan:Qilu University of Technology,2016 (in Chinese).(高超.基于席夫碱结构的Al3+荧光探针的制备及其性能研究[D].济南:齐鲁工业大学,2016.)
[19] Ding G H,Zhang X S,Fan R M.Synthesis and Fluorescence Performance of Transition Metal Complexes with Chiff Base [J].Chin J Synth Chem,2010,18(2):259-261 (in Chinese).(丁国华,张晓松,樊润梅.席夫碱过渡金属配合物的合成及其荧光性能[J].合成化学,2010,18(2):259-261.)
[20] Gong C X,Wei X P,Li J P.Fabrication and Application in SCN- Detection of Copper(Ⅱ) Ionic Selective Electrode Based on Salicylaldehyde-1,2-phenylenediamine Sensitive Membrane [J].Chin J Appl Chem,2010,27(8):950-954 (in Chinese).(巩春侠,魏小平,李建平.水杨醛缩邻苯二胺双席夫碱敏感膜Cu(Ⅱ)离子选择性电极及SCN-的测定[J].应用化学,2010,27(8):950-954.)
[21] Yang L L.Synthesis of New Carbazolebased Schiff Base Derivatives and Their Ion Recognition Properties [D].Hefei:Anhui University,2013 (in Chinese).(杨莲莲.新型咔唑基席夫碱衍生物的合成及离子识别性能研究[D].合肥:安徽大学,2013.)
[22] Wang G Q.Heterocyclic Schiff Bases as Al3+,Mg2+,Cu2+,Zn2+ Ion Probe Synthesis and Properties Study [D].Lanzhou:Lanzhou University,2016 (in Chinese).(王冠群.杂环类席夫碱作为Al3+,Mg2+,Cu2+,Zn2+离子探针的合成及其性质研究[D].兰州:兰州大学,2016.)
[23] Hou P G,Lu C H.Progress in the Application of Infrared Spectroscopy in the Identification of Pharmaceutical Preparations [J].Chin J Hosp Pharm,2013,33(8):648-649 (in Chinese).(侯鹏高,吕长淮.红外光谱法在药物制剂鉴别中的应用研究进展[J].中国医院药学杂志,2013,33(8):648-649.)