二氨基马来腈席夫碱Al~(3+)荧光分子探针
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摘要
以2,4-二羟基苯甲醛和二氨基马来腈为原料合成了Schiff碱型荧光分子探针L,采用FT-IR、~1H NMR和MS对其结构进行了表征.结果表明:在V(乙醇)∶V(4-羟乙基哌嗪乙磺酸)=95∶5(pH=7.2)缓冲溶液中,L能够通过off-on荧光响应选择性识别Al~(3+),且几乎不受其他金属离子的干扰.在Al~(3+)浓度为0~2.4×10-5 mol/L时,溶液荧光强度与Al~(3+)浓度呈现良好的线性关系.L对Al~(3+)检出限为6.693×10~(-9)mol/L,二者的络合常数为2.146×10~4(mol/L)~(-1).
In this paper, a Schiff base fluorescent probe L was prepared from 2, 4-dihydroxybenzaldehyde and 2, 3-diaminomaleonitrile. It was characterized by FT-IR,~1H NMR and MS. Subsequently, L was applied as a fluorescent probe for Al~(3+)in ethanol and 4-(2-hydroxyethyl)-1-piperazine ethanesulfonic acid(95 ∶ 5, V/V, p H = 7.2) solution,L displayed an ″ off-on″ recognition ability for Al~(3+)with good selectivity and without obvious disturbances by other metal ions. In the concentration range of Al~(3+)from 0 to 2.4 × 10-5mol/L, the fluorescene intensity of L showed a good linear relationship with the concentration of Al~(3+). The detection limit of L for Al~(3+)is 6.693 × 10-9mol/L and the binding constant between them is 2.146 × 104(mol/L)~(-1).
In this paper, a Schiff base fluorescent probe L was prepared from 2, 4-dihydroxybenzaldehyde and 2, 3-diaminomaleonitrile. It was characterized by FT-IR,~1H NMR and MS. Subsequently, L was applied as a fluorescent probe for Al~(3+)in ethanol and 4-(2-hydroxyethyl)-1-piperazine ethanesulfonic acid(95 ∶ 5, V/V, p H = 7.2) solution,L displayed an ″ off-on″ recognition ability for Al~(3+)with good selectivity and without obvious disturbances by other metal ions. In the concentration range of Al~(3+)from 0 to 2.4 × 10-5mol/L, the fluorescene intensity of L showed a good linear relationship with the concentration of Al~(3+). The detection limit of L for Al~(3+)is 6.693 × 10-9mol/L and the binding constant between them is 2.146 × 104(mol/L)~(-1).
引文
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[17]马文辉,韩宏彦,徐群,等.香豆素类荧光增强型Cu2+荧光分子探针[J].精细化工,2012,29(5):425-428.
[18]丁宝辰,朱红军,李小墨,等.以香豆素为母体的荧光探针的合成、离子识别及拟合计算研究[J].精细化工,2014,31(6):695-698.
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[20]高勇,张敏,郭斌.罗丹明荧光探针在生化分析中的应用[J].化学通报,2009(1):15-19.
[21]夏帅.合成罗丹明B类衍生物荧光探针及利用Smiles重排合成苯并噁嗪酮类血小板聚集抑制剂[D].重庆:西南大学,2015.
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[23]BHOWMICK R,DOLAI M,MISTRI T,et al.A novel pyrene-2-(pyridin-2-ylmethylsulfanyl)ethylamine based turn-on dual sensor for Al3+:experimental and computational studies[J].RSC Advance,2014,4(79):41784-41792.
[24]RAZI S S,ALI R,SRIVASTAVA P,et al.A selective quinoline-derived fluorescent chemodosimeter to detect cyanide in aqueous medium[J].Tetrahedron Letters,2014,55(5):1052-1056.
[25]廖真川.含氮杂环配体作为铝离子荧光探针及其Gd(Ⅲ)Mn(Ⅱ)配合物的磁共振成像造影剂性质研究[D].兰州:兰州大学,2014.
[26]周莹.新型含氮杂环荧光分子的设计、合成及性质研究[D].大连:大连理工大学,2008.
[27]KHANSARI M E,WALLACE K D,HOSSAIN M D.Synthesis and anion recognition studies of a dipodal thioureabased sensor for anions[J].Tetrahedron Letters,2014,55(2):438-440.
[28]CHEREDDY N R,NAGARAJU P,RAJU M V,et al.A novel FRET′off-on′fluorescent probe for the selective detection of Fe3+,Al3+and Cr3+ions:its ultra fast energy transfer kinetics and application in live cell imaging[J].Biosensors and Bioelectronics,2015,68(15):749-756.
[29]毛国江.基于香豆素、萘等衍生物的新型荧光探针的设计合成与应用研究[D].长沙:湖南大学,2014.
[30]周晓燕.酰胺和喹啉类配体配合物的合成、表征及荧光性质研究[D].兰州:兰州大学,2012.
[31]ZHU J L,ZHANG Y H,WANG L,et al.A simple turnon Schiff base fluorescence sensor for aluminumion[J].Tetrahedron Letters,2016,57(31):3535-3539.
[32]ZHOU D,SUN C Y,CHEN C,et al.Research of a highly selective fluorescent chemosensor for aluminum(III)ions based on photoinduced electron transfer[J].Journal of Molecular Structure,2015,1079(5):315-320.
[33]FAN L,LI T R,WANG B D,et al.A colorimetric and turn-on fluorescent chemosensor for Al(III)based on a chromone Schiff-base[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2013,118c(2):760-764.
[34]CROSBY G A,DEMASA J N.Measurement of photoluminescence quantum yields.Review[J].Journal of Physical Chemistry,1971,75(8):991-1024.
[35]BENESI H A,HILDEBRAND J H.A spectrophotometric investigation of the interaction of iodine with Aromatic hydrocarbons[J].Journal of the American Chemical Society,1949,71(8):2703-2707.
[36]LOUKAS Y L.Multiple complex formation of fluorescent compounds with cyclodextrins:efficient determination and evaluation of the binding constant with improved fluorometric studies[J].Analyst,1997,122(4):377-388.
[37]JISHA V S,THOMAS A J,RAMAIAH D.Fluorescence ratiometric selective recognition of Cu2+ions by dansylnaphthalimide dyads[J].Journal of Organic Chemistry,2009,74(17):6667-6673.
[38]HAKONEN A.Plasmon enhancement and surface wave quenching for phase ratiometry in coextraction-based fluorosensors[J].Analytical Chemistry,2009,81(11):4555-4559.
[2]江玉亮,邱道骥,吴婧,等.中氮茚衍生物对金属离子选择识别性的研究[J].南京师大学报(自然科学版),2008,31(3):68-70.
[3]LAKOWICZ J R.Topics in fluorescence spectroscopy:probe design and chemical sensing[M].New York:Kluwer Academic Publishers,2002:4.
[4]SONI M G,WHITE S M,FLAMM W G,et al.Safety evaluation of dietary aluminum[J].Regulatory Toxicology and Pharmacol,2001,33(1):66-79.
[5]PERL D P,BRODY A R.Alzheimer′s disease:X-ray spectrometric evidence of aluminum accumulation in neurofibrillary tangle-bearing neurons[J].Science,1980,208(4441):297-299.
[6]CRONAN C S,WALKER W J,BLOOM P R.Predicting aqueous aluminium concentrations in natural waters[J].Nature,1986,324(6093):140-143.
[7]PERL D P,GAJDUSEK D C,GARRUTO R M,et al.Intraneuronal aluminum accumulation in amyotrophic lateral sclerosis and Parkinsonism-dementia of Guam[J].Science,1982,217(4564):1053-1055.
[8]POLIZZI S,PIRA E,FERRARA M,et al.Neurotoxic effects of aluminium among foundry workers and alzheimer′s disease[J].Neurotoxicology,2002,23(6):761-774.
[9]WALTON J R.Aluminum in hippocampal neurons from humans with Alzheimer′s disease[J].Neurotoxicology,2006,27(3):385-394.
[10]RONDEAU V,JACQMIN-GADDA H,COMMENGES D,et al.Aluminum and silica in drinking water and the risk of alzheimer′s disease or cognitive decline:findings from 15-year follow-up of the PAQUID cohort[J].American Journal of Epidemiology,2009,169(4):489-496.
[11]TAYLOR A,BRANCH S,DAY M D,et al.Atomic spectrometry update.Clinical and biological materials,foods and beverages[J].Journal of Analytical Atomic Spectrometry,2008,23:595-646.
[12]QUIONERO J,MONGAY C,de la GUARDIA M.Determination of aluminum at the parts per billion level by solvent extraction and flame atomic emission spectrometry[J].Microchemical Journal,1991,43(3):213-221.
[13]CAI Q T,KHOO S B.Determination of trace aluminium by differential pulse adsorptive stripping voltammetry of aluminium(II)-8-hydroxyquinoline complex[J].Analytica Chimica Acta,1993,276(1):99-108.
[14]SANTOS W J R,SOUSA A L,LUZ R C S,et al.Amperometric sensor for nitrite using a glassy carbon electrode modified with alternating layers of iron(III)tetra-(Nmethyl-4-pyridyl)-porphyrin and cobalt(II)tetrasulfonated phthalocyanine[J].Talanta,2006,70(3):588-594.
[15]NEWBERY J E,de HADDAD M P L.Amperometric determination of nitrite by oxidation at a glassy carbon electrode[J].Analyst,1985,110(1):81-82.
[16]魏荣严,赵峰,严世强.基于罗丹明B的off-on型席夫碱荧光探针的研究[J].精细化工,2013,30(10):1169-1172.
[17]马文辉,韩宏彦,徐群,等.香豆素类荧光增强型Cu2+荧光分子探针[J].精细化工,2012,29(5):425-428.
[18]丁宝辰,朱红军,李小墨,等.以香豆素为母体的荧光探针的合成、离子识别及拟合计算研究[J].精细化工,2014,31(6):695-698.
[19]袁跃华,田茂忠,冯锋,等.罗丹明类阳离子荧光探针[J].化学进展,2010,22(10):1929-1939.
[20]高勇,张敏,郭斌.罗丹明荧光探针在生化分析中的应用[J].化学通报,2009(1):15-19.
[21]夏帅.合成罗丹明B类衍生物荧光探针及利用Smiles重排合成苯并噁嗪酮类血小板聚集抑制剂[D].重庆:西南大学,2015.
[22]蔡松涛.基于罗丹明和蒽醌类荧光分子探针的合成及其识别性能[D].天津:天津理工大学,2013.
[23]BHOWMICK R,DOLAI M,MISTRI T,et al.A novel pyrene-2-(pyridin-2-ylmethylsulfanyl)ethylamine based turn-on dual sensor for Al3+:experimental and computational studies[J].RSC Advance,2014,4(79):41784-41792.
[24]RAZI S S,ALI R,SRIVASTAVA P,et al.A selective quinoline-derived fluorescent chemodosimeter to detect cyanide in aqueous medium[J].Tetrahedron Letters,2014,55(5):1052-1056.
[25]廖真川.含氮杂环配体作为铝离子荧光探针及其Gd(Ⅲ)Mn(Ⅱ)配合物的磁共振成像造影剂性质研究[D].兰州:兰州大学,2014.
[26]周莹.新型含氮杂环荧光分子的设计、合成及性质研究[D].大连:大连理工大学,2008.
[27]KHANSARI M E,WALLACE K D,HOSSAIN M D.Synthesis and anion recognition studies of a dipodal thioureabased sensor for anions[J].Tetrahedron Letters,2014,55(2):438-440.
[28]CHEREDDY N R,NAGARAJU P,RAJU M V,et al.A novel FRET′off-on′fluorescent probe for the selective detection of Fe3+,Al3+and Cr3+ions:its ultra fast energy transfer kinetics and application in live cell imaging[J].Biosensors and Bioelectronics,2015,68(15):749-756.
[29]毛国江.基于香豆素、萘等衍生物的新型荧光探针的设计合成与应用研究[D].长沙:湖南大学,2014.
[30]周晓燕.酰胺和喹啉类配体配合物的合成、表征及荧光性质研究[D].兰州:兰州大学,2012.
[31]ZHU J L,ZHANG Y H,WANG L,et al.A simple turnon Schiff base fluorescence sensor for aluminumion[J].Tetrahedron Letters,2016,57(31):3535-3539.
[32]ZHOU D,SUN C Y,CHEN C,et al.Research of a highly selective fluorescent chemosensor for aluminum(III)ions based on photoinduced electron transfer[J].Journal of Molecular Structure,2015,1079(5):315-320.
[33]FAN L,LI T R,WANG B D,et al.A colorimetric and turn-on fluorescent chemosensor for Al(III)based on a chromone Schiff-base[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2013,118c(2):760-764.
[34]CROSBY G A,DEMASA J N.Measurement of photoluminescence quantum yields.Review[J].Journal of Physical Chemistry,1971,75(8):991-1024.
[35]BENESI H A,HILDEBRAND J H.A spectrophotometric investigation of the interaction of iodine with Aromatic hydrocarbons[J].Journal of the American Chemical Society,1949,71(8):2703-2707.
[36]LOUKAS Y L.Multiple complex formation of fluorescent compounds with cyclodextrins:efficient determination and evaluation of the binding constant with improved fluorometric studies[J].Analyst,1997,122(4):377-388.
[37]JISHA V S,THOMAS A J,RAMAIAH D.Fluorescence ratiometric selective recognition of Cu2+ions by dansylnaphthalimide dyads[J].Journal of Organic Chemistry,2009,74(17):6667-6673.
[38]HAKONEN A.Plasmon enhancement and surface wave quenching for phase ratiometry in coextraction-based fluorosensors[J].Analytical Chemistry,2009,81(11):4555-4559.