4-磺酸基苯偶氮8-羟基喹啉对不同溶剂中阴离子的识别行为研究
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摘要
为了制备一种能适应强极性溶剂和具有良好离子识别效果的喹啉偶氮衍生物,以8-羟基喹啉、对氨基苯磺酸等为原料合成了4-磺酸基苯偶氮8-羟基喹啉(SUL-8Hq)主体.通过红外、紫外研究了其结构及其与多种阴离子的相互作用行为,建立了一种灵敏度高、选择性好并能裸眼检测传感阴离子的新体系.结果表明:在乙腈中,SUL-8Hq可以识别H2PO4-,在310nm处出现新峰,其强度与H2PO-4离子浓度成正比.在水中可以识别OCl-,在472nm的吸收峰随OCl-浓度的增加而逐渐增强.在甲醇中,它可以识别HPO2-4和OCl-,且识别过程出现的新吸收峰峰值与识别离子浓度均呈现良好的线性关系.通过研究主体对不同极性溶剂中的阴离子的识别规律,为构建新型识别体系提供了一种新方法.
In order to prepare quinoline azo derivatives which could dissolve in strong polar solvent and used as subject recognition of anions in solvents,4-sulfonic acid benzene azo 8-hydroxyquinoline was synthesized using 8-hydroxyquinoline and p-aminobenzenesulfonic acid as raw materials.The structure and behavior of 8-hydroxyquinoline which interacts with many ions was studied by infrared spectrum and UV-Vis spectra.A new system of anion recognition was constructed which possessed high selectivity,good sensitivity and ablitity to detect and conduct negative ions by naked eyes.The result showed that H2 PO-4 could be recognized by SUL-8 Hq in acetonitrile,and a new peak appeared at 310 nm,whose intensity was directly proportional to the concentration of H2 PO-4 ion.OCl-was recognized by SUL-8 Hq in water,with the absorption peak at472 nm increasing with the concentration of OCl-ion.HPO2-4 and OCl-were also able to be recognized in methanol,and better linear relation was observed between new emerging absorption peak value during recognition process and recognized ion concentration.A new method was offered for constructing new recognition system by studying ion recognition principles in different polar solvents.
In order to prepare quinoline azo derivatives which could dissolve in strong polar solvent and used as subject recognition of anions in solvents,4-sulfonic acid benzene azo 8-hydroxyquinoline was synthesized using 8-hydroxyquinoline and p-aminobenzenesulfonic acid as raw materials.The structure and behavior of 8-hydroxyquinoline which interacts with many ions was studied by infrared spectrum and UV-Vis spectra.A new system of anion recognition was constructed which possessed high selectivity,good sensitivity and ablitity to detect and conduct negative ions by naked eyes.The result showed that H2 PO-4 could be recognized by SUL-8 Hq in acetonitrile,and a new peak appeared at 310 nm,whose intensity was directly proportional to the concentration of H2 PO-4 ion.OCl-was recognized by SUL-8 Hq in water,with the absorption peak at472 nm increasing with the concentration of OCl-ion.HPO2-4 and OCl-were also able to be recognized in methanol,and better linear relation was observed between new emerging absorption peak value during recognition process and recognized ion concentration.A new method was offered for constructing new recognition system by studying ion recognition principles in different polar solvents.
引文
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[3] LIU G,SHAO J.Fluorescence anion sensors based on combination of conformational restriction and photo-induced electron transfer[J].Journal of Luminescence,2013,135:312-317.
[4] TSUI Y K,DEVARAJ S,YEN Y P.Azo dyes featuring with nitrobenzoxadiazole(NBD)unit:A new selective chromogenic and fluorogenic sensor for cyanide ion[J].Sensors and Actuators B:Chemical,2012,161(1):510-519.
[5] MOHAMMADI A,DEHGHAN Z,RASSA M,et al.Colorimetric probes based on bioactive organic dyes for selective sensing of cyanide and fluoride ions[J].Sensors and Actuators B:Chemical,2016,230:388-397.
[6] CHANDEL M,ROY S M,SHARMA D,et al.Anion recognition ability of a novel azo dye derived from 4-hydroxycoumarin[J].Journal of Luminescence,2014,154:515-519.
[7] HUANG W W,LI Y P,LIN H,et al.A novel acetate selective chromog-charge neutral azo derivatives[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2012,86:437-442.
[8] WEI T B,WANG J,ZHANG Y M.The hydrogen sulfate recognition properties of azo-salicylaldehyde Schiff based receptors[J].Science China,2008,38(8);694-699.
[9] PANITSIRI A,TONGKHAN S,RADCHATAWEDCHAKOON W,et al.Synthesis and anion recognition studies of novel bis(4-hydroxycoumarin)methane azo dyes[J].Journal of Molecular Structure,2016,1107:14-18.
[10] KARAUSHA N N,MINAEVA V A,BARYSHNIKOVAB G V,et al.Identification of tautomeric intermediates of a novel thiazolylazonaphthol dye——A density functional theory study[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2018,203:324-332.
[11] HRISTOVA S,DENEVA V,PITTELKOW M,et al.A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols[J].Dyes and Pigments,2018,156:91-99.
[12] WANG Y Y,ZHAO X L,QIAN H F,et al.Mono/double3-methoxypropan-1-amine substituted pyridone azo dyes having isomeric ortho/para-aminobenzoic acids and corresponding methyl esters components[J].Dyes and Pigments,2018,153:44-52.
[13] UDHAYAKUMARIA D,VELMATHIA S,BOOBALAN M S,et al.Novel chemosensor for multiple target anions:The detection of F-and CN-ion via different approach[J].Journal of Fluorine Chemistry,2015,175:180-184.
[14] LI Y P,LI J W,LIN H,et al.A novel colorimetric receptor responding AcO-anions based on an azo derivative in DMSO and DMSO/water solution[J].Journal of Luminescence,2010,130(3):466-472.
[15]聂丽,胡蕾,傅绪成,等.N-(2,4-二硝基苯基)-N’-取代苯腙衍生物对阴离子识别研究[J].化学学报,2011,69(1):71-76.NIE L,HU L,FU X C,et al.Synthesis of N-(2,4-dinitrophenyl)-N′-(substituted-phenyl)hydrazones and their anion sensing[J].Journal of Chinese Chemical Society,2011,69(1):71-76.(Ch).