以4-硝基苯肼、8-羟基喹哪啶等为原料设计合成了8-羟基-2-喹啉甲醛-4-硝基苯腙(1),经元素分析、1 H NMR 对其结构进行了表征。在V (二甲亚砜)/V (甲醇)=1∶9混合溶剂中采用 UV-Vis 光谱法研究了苯腙(1)对 Li+、K+、Mg2+、Ca2+、Mn2+、Co2+、Ni2+、Zn2+、Cd2+、Hg2+、Fe2+、Fe3+及 Cu2+离子的识别性能。结果表明,苯腙1仅对 Cu2+和 Zn2+有特殊的识别能力,加入 Cu2+或 Zn2+的苯腙1溶液由黄色分别变为橙色和红色,其光谱在413 nm 处的吸收峰强度减小,且分别在485和508 nm 附近产生新的吸收峰。竞争实验表明,苯腙1对 Zn2+的检测不受除 Cu2+以外上述其它阳离子影响,而对 Cu2+的检测不受上述任何其它阳离子的影响。线性拟合结果显示,苯腙1与 Cu2+和 Zn2+ 分别形成了1∶1和1∶2的配合物。
8-hydroxy-2-quinoline formaldehyde-4-nitrophenylhydrazone (1)was synthesized by using 4-nitrophe-nyl hydrazine and 8-hydroxyquinaldine as starting materials and its structure was characterized by elemental analysis,1 H NMR.The influence of Li+ ,K+ ,Mg2 + ,Ca2 + ,Mn2 + ,Co2 + ,Ni2 + ,Zn2 + ,Cd2 + ,Hg2 + ,Fe2 + , Fe3 + and Cu2 + on the spectra of phenylhydrazone 1 were investigated by the UV-Vis spectrum method in V (DMSO)/V (methanol)=1 ∶9 mixed solvent.The result indicated that the UV-Vis spectra of phenylhydra-zone 1 only behaved special recognition and sensitivity to Cu2 + and Zn2 + .The color of phenylhydrazone 1 was changed from yellow to orange or red upon adding Cu2 + or Zn2 + respectively,which resulted in the decrease in the absorption at 413 nm and the new absorption near 485 nm and 508 nm.Competition experiments indicated that other cations but Cu2 + had no effect on the detection of Zn2 + ,while the presence of other ions had no effect on the detection of Cu2 + .The fitting results of linear display that the 1 ∶1 and 1 ∶2 binding stoichiometry of phenylhydrazone 1 with Cu2 + and Zn2 + respectively.
参考文献
[1] | Jianjun Du;Mingming Hu;Jiangli Fan .Fluorescent chemodosimeters using "mild" chemical events for the detection of small anions and cations in biological and environmental media[J].Chemical Society Reviews,2012(12):4511-4535. |
[2] | Cai Yulei;Meng Xiangming;Wang Shuxin et al.A quinoline based fluorescent probe that can distinguish zinc(Ⅱ)from cadmium(Ⅱ)in water[J].Tetrahedron Let-ters,2013,54(9):1125-1128. |
[3] | Xinxiu Fang;Guiyan Zhao;Yanmeng Xiao .A Europium-based luminescent chemosensor for Zn~(2+) with quinoxaline as the antenna[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2013(8):806-810. |
[4] | Lijun Tang;Jia Zhao;Mingjun Cai .An efficient sensor for relay recognition of Zn~(2+) and Cu~(2+) through fluorescence 'off-on-off functionality[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2013(45):6105-6109. |
[5] | 赵秀文,张亚男,何广杰,周硼.基于香豆酰肼的高选择性的铜离子荧光探针[J].发光学报,2010(03):433-438. |
[6] | 魏太保,李军舰,林奇,姚虹,郭英,白翠冰,谢永强,张有明.N-芳基香豆素甲基酮缩氨基硫脲对Cu2+的选择性比色识别[J].高等学校化学学报,2012(11):2452-2456. |
[7] | Rollas Sevim;Kü?ükgüzel?Güniz .Biological activities of hydrazone derivatives[J].MOLECULES,2007,12(8):1910-1939. |
[8] | Xin Su;Ivan Aprahamian .Hydrazone-based switches, metallo-assemblies and sensors[J].Chemical Society Reviews,2014(6):1963-1981. |
[9] | Jin, Y.-X.;Zhong, A.-G.;Zhang, Y.-J.;Pan, F.-Y. .Synthesis, crystal structure, spectroscopic properties, antibacterial activity and theoretical studies of a novel difunctional acylhydrazone[J].Journal of Molecular Structure,2011(1/3):45-50. |
[10] | 邹敏,卢俊瑞,辛春伟,鲍秀荣,杨波,朱姗姗,刘倩,李迎辉,陶继强.1-(2-羟基苯甲酰基)-3-甲基-4-取代苯腙基-吡唑啉酮及其中间体的合成、表征及抑菌活性[J].有机化学,2010(08):1201-1206. |
[11] | Mangalam Neema Ani;Sheeja S R;Prathapachandra Kurup M R .Mn(Ⅱ)complexes of some acylhydrazones with NNO donor sites:syntheses,a spectroscopic view on their coordination possibilities and crystal structures[J].POLYHEDRON,2010,29(18):3318-3323. |
[12] | Paschalidis Damianos G;Tossidis Ioannis A;Gdaniec Maria .Synthesis,characterization and spectra of lantha-nide(Ⅲ)hydrazone complexes The X-ray molecular structures of the erbium(Ⅲ)complex and the ligand[J].POLYHEDRON,2000,1 9(26-27):2629-2637. |
[13] | Mathew, N.;Kurup, M.R.P. .Synthesis and characterization of Mo(VI) complexes derived from ONO donor acylhydrazones[J].Spectrochimica acta, Part A. Molecular and biomolecular spectroscopy,2011(5):1424-1428. |
[14] | 吴海强,王宇,谭新强,罗静,刘晓亚.基于罗丹明的水溶性Cu~(2+)传感探针的合成与性能[J].功能材料,2012(24):3468-3471. |
[15] | Mathew Nancy;Sithambaresan Maheswaran;Pratha-pachandra Kurup M R .Spectral studies of copper(Ⅱ)complexes of tridentate acylhydrazone ligands withhet-erocyclic compounds as coligands:X-ray crystal struc-ture of oneacylhydrazone copper(Ⅱ)complex[J].Spec-trochimica Acta Part A,2011,79(5):1154-1161. |
[16] | Peng Zhang;BingBing Shi;XingMei You;YouMing Zhang;Qi Lin;Hong Yao;TaiBao Wei .A highly selective and sensitive chemosensor for instant detection cyanide via different channels in aqueous solution[J].Tetrahedron,2014(10):1889-1894. |
[17] | Shengju Ou;Zhihua Lin;Chunying Duan .A sugar-quinoline fluorescent chemosensor for selective detection of Hg~(2+)ion in natural water[J].Chemical communications,2006(42):4392-4394. |
[18] | Yasuhiro Shiraishi;Shigehiro Sumiya;Kohno Yoshiko et al.A Rhodamine cyclen conjugate as a highly sensi-tive and selective fluorescent chemosensor for Hg(Ⅱ)(and supporting information)[J].Journal of Organical Chemistry,2008,73(21):8571-8574. |
[19] | Li, AF;He, H;Ruan, YB;Wen, ZC;Zhao, JS;Jiang, QJ;Jiang, YB .Oxidative cyclization of N-acylhydrazones. Development of highly selective turn-on fluorescent chemodosimeters for Cu2+[J].Organic & biomolecular chemistry,2009(1):193-200. |
[20] | Liu, Yong-chun;Yang, Zheng-yin .Crystal structures, antioxidation and DNA binding properties of Yb(III) complexes with Schiff-base ligands derived from 8-hydroxyquinoline-2-carbaldehyde and four aroylhydrazines[J].BioMetals: An International Journal on the Role of Metal Ions in Biology, Biochemistry and Medicine,2009(5):733-751. |
[21] | Liu Yongchun;Yang Zhengyin .Antioxidation and DNA binding properties of binuclear Nd(Ⅲ)complexes with Schiff-base ligands derived from 8-hydroxyquinoline-2-carboxyaldehyde and four aroylhydrazides[J].Inorganic Chemistry Communications,2009,12(8):704-706. |
- 下载量()
- 访问量()
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%