菲并咪唑-水杨醛席夫碱分子探针对Fe~(3+)、Cr~(3+)、Al~(3+)的检测
|
摘要
基于菲并咪唑-水杨醛合成了分子探针SL,并用NMR、IR对其结构进行了确证。实验结果表明,探针SL对三价金属离子铁、铬、铝(Fe~(3+)、Cr~(3+)、Al~(3+))的识别具有较好的选择性和较高的灵敏度,并且几乎不受一价、二价离子的干扰。使用Job’s Plots法证明,探针SL与Fe~(3+)、Al~(3+)的结合比均为1:1,与Cr~(3+)的结合比为2:3,对Fe~(3+)、Cr~(3+)、Al~(3+)的检出限分别为3.09×10~(-8),4.82×10~(-8),2.89×10~(-8)mol/L。利用荧光光谱法探讨了探针SL对剧毒Cr~(3+)的检测行为,发现探针SL对Cr~(3+)离子有较好的选择性和灵敏度,是一种具有潜在应用价值的Cr~(3+)荧光探针。
A design, together with a synthesis, has been made of molecular probe SL based on phenamidazolesalicylaldehyde multifunctional molecular probe SL, with its structure confirmed by NMR and IR. These results show that the probe SL is characterized with a fine selectivity and sensitivity performance as for the identification of trivalent metal ions, such as iron(III), chromium(III), aluminum(III)(Fe~(3+), Cr~(3+), Al~(3+)), hardly undisturbed by the monovalent and divalent ions. The Job's Plots method verifies a binding ratio of 1:1 of probe SL to Fe~(3+) and Al~(3+) and a binding ratio of 2:3 to Cr~(3+). The detection limits of Fe~(3+), Cr~(3+), and Al~(3+) are 3.09×10~(-8) mol/L, 4.82×10~(-8) mol/L, 2.89×10~(-8) mol/L, respectively. Then, the detection of the highly toxic Cr~(3+) by the probe SL has been investigated by fluorescence spectroscopy. It is found that the probe SL has a good selectivity and sensitivity to the Cr~(3+) ion, proving it to be a Cr~(3+)fluorescence probe with potential application value.
A design, together with a synthesis, has been made of molecular probe SL based on phenamidazolesalicylaldehyde multifunctional molecular probe SL, with its structure confirmed by NMR and IR. These results show that the probe SL is characterized with a fine selectivity and sensitivity performance as for the identification of trivalent metal ions, such as iron(III), chromium(III), aluminum(III)(Fe~(3+), Cr~(3+), Al~(3+)), hardly undisturbed by the monovalent and divalent ions. The Job's Plots method verifies a binding ratio of 1:1 of probe SL to Fe~(3+) and Al~(3+) and a binding ratio of 2:3 to Cr~(3+). The detection limits of Fe~(3+), Cr~(3+), and Al~(3+) are 3.09×10~(-8) mol/L, 4.82×10~(-8) mol/L, 2.89×10~(-8) mol/L, respectively. Then, the detection of the highly toxic Cr~(3+) by the probe SL has been investigated by fluorescence spectroscopy. It is found that the probe SL has a good selectivity and sensitivity to the Cr~(3+) ion, proving it to be a Cr~(3+)fluorescence probe with potential application value.
引文
[1]ZHOU T,CHEN X X,HUA Q H,et al.Synthesis and Evaluation of a New Furfuran-Based Rhodamine BFluorescent Chemosensor for Selective Detection of Fe3+and Its Application in Living-Cell Imaging[J].Sensors and Actuators B:Chemical,2017,253:292-301.
[2]WEI R Y,WEI Z W,SUN L N,et al.Nile Red Derivative-Modified Nanostructure for Upconversion Luminescence Sensing and Intracellular Detection of Fe3+and MR Imaging[J].ACS Applied Materials&Interfaces,2016,8(1):400-410.
[3]CAIRO G,PIETRANGELO A.Iron Regulatory Proteins in Pathobiology[J].Biochemical Journal,2000,352(2):241-250.
[4]SINGH A K,GUPTA V K,GUPTA B.Chromium(III)Selective Membrane Sensors Based on Schiff Bases As Chelating Ionophores[J].Analytica Chimica Acta,2007,585(1):171-178.
[5]ZHANG H,ZHANG G,XU J K,et al.Highly Sensitive“Turn-On”Fluorescent Chemical Sensor for Trace Analysis of Cr3+Using Electro-Synthesized Poly(N-(9-Fluorenylmethoxycarbonyl)-L-Histidine)[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2018,191:79-87.
[6]侯淑华,曲忠国,钟克利,等.一种苯并噻唑-罗丹明衍生物的合成及其对Fe3+、Al3+、Cr3+的识别[J].有机化学,2016,36(4):768-773.HOU Shuhua,QU Zhongguo,ZHONG Keli,et al.Synthesis of a Novel Benzothiazole-Rhodamine Derivative and Its Selective Detection of Fe3+,Al3+and Cr3+[J].Chinese Journal of Organic Chemistry,2016,36(4):768-773.
[7]ZHU Z X,YU D D,LIU Z G,et al.A Naphthalene Derivative As‘Turn-On’Fluorescent Chemosensor for the Highly Selective and Sensitive Detection of Al3+[J].Luminescence,2017,32(7):1307-1312.
[8]罗秘兰,钟伟通,曾贤桂,等.用电感耦合等离子光谱发生仪测定水中铜、铅、锌、铬、镉、镍含量的不确定度分析[J].广东化工,2013,40(1):114-116,98.LUO Milan,ZHONG Weitong,ZENG Xiangui,et al.Using Inductively Coupled Plasma Spectrum Analyzer to Measure the Water Happened Copper,Lead,Zinc,Chromium,Cadmium,Nickel Content of Uncertainty Analysis[J].Guangdong Chemical Industry,2013,40(1):114-116,98.
[9]杨晓婧,李美丽,白建华,等.火焰原子吸收光谱法测定废水中的重金属离子[J].光谱实验室,2010,27(1):247-249.YANG Xiaojing,LI Meili,BAI Jianhua,et al.Determination of Heavy Metal Ions in Waste Water by the Flame Atomic Absorption Spectrometry[J].Chinese Journal of Spectroscopy Laboratory,2010,27(1):247-249.
[10]霍晶.离子色谱法测定水中7种阴离子[J].中国无机分析化学,2014,4(2):8-10.HUO Jing.Determination of Seven Types of Anions in Water by Ion Chromatography[J].Chinese Journal of Inorganic Analytical Chemistry,2014,4(2):8-10.
[11]罗莹,刘有智,祁贵生,等.紫外可见分光光度法测定络合铁离子浓度[J].天然气化工,2013,38(5):75-78,84.L U O Yi n g,L I U Yo u z h i,Q I G u i s h e n g,e t a l.A p p l i c a t i o n o f U V-Vi s S p e c t r o p h o t o m e t r y f o r Determination of Chelated Iron Concentration[J].Natural Gas Chemical Industry,2013,38(5):75-78,84.
[12]冯素玲,唐安娜,樊静.荧光分析法测定痕量铬(Ⅵ)[J].分析化学,2001,29(5):558-560.FENG Suling,TANG Anna,FAN Jing.A Fluorimetric Method for Determination of Chromium(Ⅵ)[J].Chinese Journal of Analytical Chemistry,2001,29(5):558-560.
[13]魏颖.芳香性双亲配体的合成与金属离子的检测识别[D].大连:大连理工大学,2015.WEI Ying.The Synthesis of Aromaticity Parents Ligands and the Detection of the Metal Ions[D].Dalian:Dalian University of Technology,2015.
[14]LI C L,WANG S P,CHEN W P,et al.High Performance Full Color OLEDs Based on a Class of Molecules with Dual Carrier Transport Channels and Small Singlet-Triplet Splitting[J].Chemical Communications,2015,51:10632-10635.
[15]ZHAO X,YIN G H,JIN D,et al.A Sensitive Colorimetric and Ratiometric Chemosensor for Trivalent Metal Cations[J].Journal of Fluorescence,2015,25(2):327-333.
[16]HOUSE J E.Calculator Program for Analysis of a Complex by Job’s Method[J].Journal of Chemical Education,1982,59(2):132.
[17]RENNY J S,TOMASEVICH L L,TALLMADGE E H,et al.Method of Continuous Variations:Applications of Job Plots to the Study of Molecular Associations in Organometallic Chemistry[J].Angewandte Chemie International Edition,2013,52(46):11998-12013.
[2]WEI R Y,WEI Z W,SUN L N,et al.Nile Red Derivative-Modified Nanostructure for Upconversion Luminescence Sensing and Intracellular Detection of Fe3+and MR Imaging[J].ACS Applied Materials&Interfaces,2016,8(1):400-410.
[3]CAIRO G,PIETRANGELO A.Iron Regulatory Proteins in Pathobiology[J].Biochemical Journal,2000,352(2):241-250.
[4]SINGH A K,GUPTA V K,GUPTA B.Chromium(III)Selective Membrane Sensors Based on Schiff Bases As Chelating Ionophores[J].Analytica Chimica Acta,2007,585(1):171-178.
[5]ZHANG H,ZHANG G,XU J K,et al.Highly Sensitive“Turn-On”Fluorescent Chemical Sensor for Trace Analysis of Cr3+Using Electro-Synthesized Poly(N-(9-Fluorenylmethoxycarbonyl)-L-Histidine)[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2018,191:79-87.
[6]侯淑华,曲忠国,钟克利,等.一种苯并噻唑-罗丹明衍生物的合成及其对Fe3+、Al3+、Cr3+的识别[J].有机化学,2016,36(4):768-773.HOU Shuhua,QU Zhongguo,ZHONG Keli,et al.Synthesis of a Novel Benzothiazole-Rhodamine Derivative and Its Selective Detection of Fe3+,Al3+and Cr3+[J].Chinese Journal of Organic Chemistry,2016,36(4):768-773.
[7]ZHU Z X,YU D D,LIU Z G,et al.A Naphthalene Derivative As‘Turn-On’Fluorescent Chemosensor for the Highly Selective and Sensitive Detection of Al3+[J].Luminescence,2017,32(7):1307-1312.
[8]罗秘兰,钟伟通,曾贤桂,等.用电感耦合等离子光谱发生仪测定水中铜、铅、锌、铬、镉、镍含量的不确定度分析[J].广东化工,2013,40(1):114-116,98.LUO Milan,ZHONG Weitong,ZENG Xiangui,et al.Using Inductively Coupled Plasma Spectrum Analyzer to Measure the Water Happened Copper,Lead,Zinc,Chromium,Cadmium,Nickel Content of Uncertainty Analysis[J].Guangdong Chemical Industry,2013,40(1):114-116,98.
[9]杨晓婧,李美丽,白建华,等.火焰原子吸收光谱法测定废水中的重金属离子[J].光谱实验室,2010,27(1):247-249.YANG Xiaojing,LI Meili,BAI Jianhua,et al.Determination of Heavy Metal Ions in Waste Water by the Flame Atomic Absorption Spectrometry[J].Chinese Journal of Spectroscopy Laboratory,2010,27(1):247-249.
[10]霍晶.离子色谱法测定水中7种阴离子[J].中国无机分析化学,2014,4(2):8-10.HUO Jing.Determination of Seven Types of Anions in Water by Ion Chromatography[J].Chinese Journal of Inorganic Analytical Chemistry,2014,4(2):8-10.
[11]罗莹,刘有智,祁贵生,等.紫外可见分光光度法测定络合铁离子浓度[J].天然气化工,2013,38(5):75-78,84.L U O Yi n g,L I U Yo u z h i,Q I G u i s h e n g,e t a l.A p p l i c a t i o n o f U V-Vi s S p e c t r o p h o t o m e t r y f o r Determination of Chelated Iron Concentration[J].Natural Gas Chemical Industry,2013,38(5):75-78,84.
[12]冯素玲,唐安娜,樊静.荧光分析法测定痕量铬(Ⅵ)[J].分析化学,2001,29(5):558-560.FENG Suling,TANG Anna,FAN Jing.A Fluorimetric Method for Determination of Chromium(Ⅵ)[J].Chinese Journal of Analytical Chemistry,2001,29(5):558-560.
[13]魏颖.芳香性双亲配体的合成与金属离子的检测识别[D].大连:大连理工大学,2015.WEI Ying.The Synthesis of Aromaticity Parents Ligands and the Detection of the Metal Ions[D].Dalian:Dalian University of Technology,2015.
[14]LI C L,WANG S P,CHEN W P,et al.High Performance Full Color OLEDs Based on a Class of Molecules with Dual Carrier Transport Channels and Small Singlet-Triplet Splitting[J].Chemical Communications,2015,51:10632-10635.
[15]ZHAO X,YIN G H,JIN D,et al.A Sensitive Colorimetric and Ratiometric Chemosensor for Trivalent Metal Cations[J].Journal of Fluorescence,2015,25(2):327-333.
[16]HOUSE J E.Calculator Program for Analysis of a Complex by Job’s Method[J].Journal of Chemical Education,1982,59(2):132.
[17]RENNY J S,TOMASEVICH L L,TALLMADGE E H,et al.Method of Continuous Variations:Applications of Job Plots to the Study of Molecular Associations in Organometallic Chemistry[J].Angewandte Chemie International Edition,2013,52(46):11998-12013.