CN109369624B - 一种巴比妥酸衍生物及其制备和在荧光识别铁离子和汞离子中的应用 - Google Patents
一种巴比妥酸衍生物及其制备和在荧光识别铁离子和汞离子中的应用 Download PDFInfo
- Publication number
- CN109369624B CN109369624B CN201811466124.3A CN201811466124A CN109369624B CN 109369624 B CN109369624 B CN 109369624B CN 201811466124 A CN201811466124 A CN 201811466124A CN 109369624 B CN109369624 B CN 109369624B
- Authority
- CN
- China
- Prior art keywords
- barbituric acid
- acid derivative
- fluorescence
- ions
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- DNZPLHRZXUJATK-UHFFFAOYSA-N 2-sulfanylidene-5-[[5-[2-(trifluoromethyl)phenyl]furan-2-yl]methyl]-1,3-diazinane-4,6-dione Chemical compound FC(F)(F)C1=CC=CC=C1C(O1)=CC=C1CC1C(=O)NC(=S)NC1=O DNZPLHRZXUJATK-UHFFFAOYSA-N 0.000 title claims abstract description 24
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title description 19
- -1 iron ions Chemical class 0.000 title description 12
- 229910052742 iron Inorganic materials 0.000 title description 9
- 229910052753 mercury Inorganic materials 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 93
- 239000000243 solution Substances 0.000 claims abstract description 35
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims abstract description 19
- DXUACWQWQDJZMY-UHFFFAOYSA-N 5-(3-nitrophenyl)furan-2-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=2OC(C=O)=CC=2)=C1 DXUACWQWQDJZMY-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000010791 quenching Methods 0.000 claims abstract description 6
- 230000008859 change Effects 0.000 claims abstract description 5
- 230000000171 quenching effect Effects 0.000 claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 150000007656 barbituric acids Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000003745 diagnosis Methods 0.000 claims 2
- 150000002500 ions Chemical class 0.000 abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 10
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000001514 detection method Methods 0.000 description 12
- 150000001768 cations Chemical class 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 102000001554 Hemoglobins Human genes 0.000 description 2
- 108010054147 Hemoglobins Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 206010022971 Iron Deficiencies Diseases 0.000 description 2
- 102000036675 Myoglobin Human genes 0.000 description 2
- 108010062374 Myoglobin Proteins 0.000 description 2
- 208000007502 anemia Diseases 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- SWKHEIHSYWZUJP-UHFFFAOYSA-N 1,3-diazinane-2,4,6-trione Chemical compound O=C1CC(=O)NC(=O)N1.O=C1CC(=O)NC(=O)N1 SWKHEIHSYWZUJP-UHFFFAOYSA-N 0.000 description 1
- 102000018832 Cytochromes Human genes 0.000 description 1
- 108010052832 Cytochromes Proteins 0.000 description 1
- 208000015710 Iron-Deficiency Anemia Diseases 0.000 description 1
- 206010025476 Malabsorption Diseases 0.000 description 1
- 208000004155 Malabsorption Syndromes Diseases 0.000 description 1
- 208000008763 Mercury poisoning Diseases 0.000 description 1
- 206010027439 Metal poisoning Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 102000000505 Ribonucleotide Reductases Human genes 0.000 description 1
- 108010041388 Ribonucleotide Reductases Proteins 0.000 description 1
- 102000019259 Succinate Dehydrogenase Human genes 0.000 description 1
- 108010012901 Succinate Dehydrogenase Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000018823 dietary intake Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000002795 fluorescence method Methods 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 244000000053 intestinal parasite Species 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000008239 natural water Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004799 sedative–hypnotic effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 238000000954 titration curve Methods 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 230000005740 tumor formation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Pathology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Molecular Biology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
本发明公开了一种基于5‑(3‑硝基苯基)呋喃‑2‑甲醛的巴比妥酸衍生物的合成方法，是在溶剂乙醇中，5‑(3‑硝基苯基)呋喃‑2‑甲醛和巴比妥酸制得。该巴比妥酸衍生物在DMSO中呈浅绿色荧光。在巴比妥酸衍生物的DMSO溶液中分别入Mg2+，Ca2+，Cr3+，Fe3+，Co2+，Ni2+，Cu2+，Zn2+，Ag+，Cd2+，Hg2+，Pb2+，Ba2+，Al3+的水溶液，只有Fe3+加入能使巴比妥酸衍生物溶液的荧光猝灭；只有Hg2+的加入能使巴比妥酸衍生物溶液的荧光增强并由绿色变为橙黄色，因此其可用于Fe3+、Hg2+的单一选择性荧光识别，这种识别性能在离子识别领域具有重要的应用价值。
Description
技术领域
本发明涉及一种巴比妥酸衍生物，尤其涉及一种基于5-(3-硝基苯基)呋喃-2-甲醛的巴比妥酸衍生物其及制备方法，主要用于单一选择性识别Fe3+和Hg2+，属于化学合成领域及阳离子检测领域。
背景技术
在化学、生物、环境等领域中，离子和分子扮演者重要的角色，对于环境中某些特殊离子或分子的检测与分离至关重要，例如：
铁（Fe），是人体不可缺少的微量元素，它是构成血红蛋白、肌红蛋白及多种酶的重要成分，如果体内缺少铁，可影响血红蛋白、肌红白蛋的合成，可使某些酶，如细胞色素C、核糖核苷酸还原酶、琥珀酸脱氢酶等的活性降低。这些酶与生物氧化、组织呼吸、神经递质的分解与合成有着密切关系。因此，铁的缺乏可引起很多生理上的变化，从而导致免疫力低下，智力降低和机体抗感染能力降低，影响机体体温调节能力，神经机能紊乱，工作效率降低等各种疾病，最常见的是缺铁性贫血。我国7岁以下儿童贫血平均患病率达51.6％，孕妇贫血率平均30％左右。主要因机体铁需要量增加、膳食摄入不足及吸收障碍引起。另外，消化道溃疡、肠道寄生虫等疾病的出血，也是引起铁缺乏的重要原因。因此，检测生命体中的铁含量具有重要的意义。
汞（Hg）及其化合物对人体健康存在多种危害，若存在于天然水体中，则会对大范围的人群以及动物造成威胁。它能够在生物体内累积，通过食物链转移到人体内。人体内累积的微量汞无法通过自身代谢进行排泄，便会直接导致心脏、肝、甲状腺疾病，引起神经系统紊乱，慢性汞中毒，甚至引发恶性肿瘤的形成。所以对它们的检测与分离也是至关重要的。
目前，人们已经研发出多种离子/分子检测的方法，并且由于荧光法具有操作简便、快捷、灵敏度高等优点，已经发展为离子/分子识别的主要检测手段。然而，在现实生活中，各种对人体有益或有害的离子/分子大都存在于水相中，而所报道的可以对离子进行检测的方法大多是在溶液中进行，对离子/分子的检测也比较局限。
巴比妥酸（Barbituric acid），又称丙二酰脲，化学名：2,4,6-嘧啶三酮。用途：可用作分析试剂、有机合成原料、塑料和染料的中间体、聚合反应的催化剂。丙二酰脲亚甲基上两个氢原子被烃基取代后的若干衍生物，称为巴比妥类药物，是一类重要的镇静催眠药物。然而，对于巴比妥酸衍生物在荧光识别阳离子的研究，目前尚未见报道。
发明内容
本发明的目的是提供一种基于5-(3-硝基苯基)呋喃-2-甲醛的巴比妥酸衍生物及其制备方法；
本发明的另一目的是提供一种该巴比妥酸衍生物作为传感器在单一选择性荧光识别Fe3+和Hg2+中的应用。
一、巴比妥酸衍生物
本发明巴比妥酸衍生物，是基于5-(3-硝基苯基)呋喃-2-甲醛的巴比妥酸衍生物，标记为SN，其结构式如下：
巴比妥酸衍生物SN的合成：在溶剂乙醇中，5-(3-硝基苯基)呋喃-2-甲醛和巴比妥酸以1:1~1:1.2的摩尔比，在72~80℃下反应6~10 h，冷却至室温，抽滤得到黄色固体，并用乙醇洗涤3~5次，所得产物即为巴比妥酸衍生物（SN）。
巴比妥酸衍生物SN的质谱和氢谱谱图见图1和图2。
二、巴比妥酸衍生物在检测Fe3+、Hg2+离子中的应用
1、SN的荧光性能
通过对巴比妥酸衍生物SN的荧光性能研究表明，SN在DMSO溶液中具有荧光发射性能：当激发波长为355nm时，SN发出浅绿色荧光（发射波长500nm）。
2、SN单一选择性荧光检测Fe3+、Hg2+
在SN的DMSO溶液（浓度为1×10-4mol/L）中，加入5倍当量（相对于SN）的Mg2+，Ca2+，Cr3+，Fe3+，Co2+，Ni2+，Cu2+，Zn2+，Ag+，Cd2+，Hg2+，Pb2+，Ba2+，和Al3+（0.1M）水溶液，观察溶液的荧光变化情况。
结果发现，只有Fe3+加入能使SN的DMSO溶液荧光猝灭；只有加入Hg2+时，SN溶液的荧光增强并由浅绿色变为橙色。
图3为SN的DMSO溶液中分别加入不同阳离子的全扫描(λex=355 nm)。由图3表明汞离子能使SN的DMSO溶液荧光增强，由浅绿色变为橙色；而铁离子能使SN的DMSO溶液荧光猝灭。
图4为SN的DMSO溶液中先加入Fe3+，在此基础上分别加入不同阳离子的抗干扰图。（从1到13依次为：Fe3+、Ag+、Al3+,Ba2+、Ca2+、Cd2+、Co2+、Cr3+、Cu2+、Mg2+、Ni2+、Pb2+、Zn2+）。图4显示的结果说明，没有汞离子存在时其他离子对铁离子的识别没有影响，但汞离子存在会对铁离子的识别有干扰。这也说明没有汞离子存在能专一性识别铁离子。
图5、6为SN的DMSO溶液中加入Fe3+的荧光滴定图及最低检测限。荧光滴定实验表明，SN的DMSO溶液对Fe3+的最低检测限分别为4.75×10-9M。
图7为SN的DMSO溶液中加入Hg2+，在此基础上分别加入不同阳离子的抗干扰图（从4到26依次为：Ag+ 、Al3+、Ba2+、Ca2+、Cd2+、Co2+、Cr3+、Cu2+、Fe3+、Mg2+、Ni2+、Pb2+、Zn2+。）。图7显示的结果说明上述离子对SN的DMSO溶液识别汞离子没有干扰，即使Fe3+存在时对Hg2+识别也没有影响。
图8、9分别为SN的DMSO溶液中加入Hg2+的荧光滴定图及加入Hg2+的最低检测限。荧光滴定实验表明，SN的DMSO溶液对Fe3+的最低检测限分别为5.2×10-9M。
3、识别机理分析
在DMSO中，巴比妥酸衍生物SN能与Fe3+、Hg2+配位分别形成配合物SN-Fe3+荧光猝灭、SN-Hg2+荧光增强。图10为SN和SN+Fe3+的红外光谱图；从图10可以看出，当Fe3+加入到主体SN后，主体N-H伸缩振动峰从3327cm-1移动到3444 cm-1，C=O伸缩振动峰从1691 cm-1移动到1649 cm-1，说明主体SN与Fe3+通过氢键作用发生了配位，致使荧光猝灭。图11为SN和SN+Hg2+的红外光谱图。从图11可以看出，当Hg2+加入到主体SN后，主体N-H伸缩振动峰从3327cm-1移动到3468 cm-1，C=O伸缩振动峰从1691 cm-1移动到1693cm-1，说明主体SN与Hg2+形成了氢键，致使荧光增强。
附图说明
图1为SN的质谱图；
图2为SN的氢谱图；
图3为SN的DMSO溶液中分别加入不同阳离子的全扫描(λex=355 nm)；
图4为SN的DMSO溶液中加入Fe3+，在此基础上分别加入不同阳离子的抗干扰图。
图5为SN的DMSO溶液中加入Fe3+的荧光滴定图；
图6为SN的DMSO溶液中加入Fe3+的最低检测限；
图7为SN的DMSO溶液中加入Hg2+，在此基础上分别加入不同阳离子的抗干扰图；
图8为SN的DMSO溶液中加入Hg2+的荧光滴定图；
图9为SN的DMSO溶液中加入Hg2+的最低检测限；
图10为SN和SN+Fe3+的红外光谱图；
图11为SN和SN+Hg2+的红外光谱图。
具体实施方式
下面通过具体实施例对本发明巴比妥酸衍生物SN的制备和荧光识别Fe3+、Hg2+的应用做进一步说明。
1、巴比妥酸衍生物SN的制备
取5-(3-硝基苯基)呋喃-2-甲醛0.152g（0.7 mmol），巴比妥酸0.09g（0.7mmol），加入到50ml乙醇中，在80℃下反应8h，冷却至室温，抽滤，得到黄色固体，用乙醇洗涤4次，得到目标化合物（SN）0.198g，产率为82%。SN合成路线为：
实施例2、SN识别Fe3+
移取2 mlSN的DMSO溶液（CSN=1×10-4M）于一系列比色管中，分别加入5倍当量Zn2+，Ni2+，Cd2+，Pb2+，Fe3+，Co2+，Ag+，Ca2+，Cu2+，Mg2+，Cr3+，Ba2+，Al3+，Hg2+的水溶液（C=0.5mM），若SN的DMSO溶液荧光猝灭，说明加入的是Fe3+，若SN溶液的荧光没有发生变化，则说明加入的不是Fe3+。
实施例3、SN识别Hg2+
移取2 mlSN的DMSO溶液（CSN=1×10-4M）溶液于一系列比色皿中，分别加入5倍当量的Zn2+，Ni2+，Cd2+，Pb2+，Fe3+，Co2+，Ag+，Ca2+，Cu2+，Mg2+，Cr3+，Ba2+，Al3+，Hg2+的水溶液，若SN溶液的荧光增强并由浅绿色变为橙色，说明加入的是Hg2+，若传感器分子的荧光没有发生变化，则说明加入的不是Hg2+。
Claims (2)
1.一种基于5-(3-硝基苯基)呋喃-2-甲醛的巴比妥酸衍生物在单一选择性荧光识别Fe3 +中的应用，其特征在于：在巴比妥酸衍生物的DMSO溶液中，分别加入Mg2+，Ca2+，Cr3+，Fe3+，Co2+，Ni2+，Cu2+，Zn2+，Ag+，Cd2+，Hg2+，Pb2+，Ba2+，Al3+的水溶液，只有Fe3+加入能使巴比妥酸衍生物DMSO溶液的荧光猝灭；所述应用是以非疾病诊断或治疗为目的；所述基于5-(3-硝基苯基)呋喃-2-甲醛的巴比妥酸衍生物，其结构式如下：
2.一种基于5-(3-硝基苯基)呋喃-2-甲醛的巴比妥酸衍生物在单一选择性荧光识别Hg2 +中的应用，其特征在于：在巴比妥酸衍生物的DMSO溶液中，分别加入Zn2+、Ni2+、Cd2+、Pb2+、Fe3+、Co2+、Ag+、Ca2+、Cu2+、Mg2+、Cr3+、Ba2+、Al3+、Hg2+的水溶液，只有Hg2+的加入能使巴比妥酸衍生物DMSO溶液的荧光增强并由绿色变为橙黄色；所述应用是以非疾病诊断或治疗为目的；所述基于5-(3-硝基苯基)呋喃-2-甲醛的巴比妥酸衍生物，其结构式如下：
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811466124.3A CN109369624B (zh) | 2018-12-03 | 2018-12-03 | 一种巴比妥酸衍生物及其制备和在荧光识别铁离子和汞离子中的应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811466124.3A CN109369624B (zh) | 2018-12-03 | 2018-12-03 | 一种巴比妥酸衍生物及其制备和在荧光识别铁离子和汞离子中的应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109369624A CN109369624A (zh) | 2019-02-22 |
| CN109369624B true CN109369624B (zh) | 2021-07-30 |
Family
ID=65375219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811466124.3A Expired - Fee Related CN109369624B (zh) | 2018-12-03 | 2018-12-03 | 一种巴比妥酸衍生物及其制备和在荧光识别铁离子和汞离子中的应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109369624B (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109942458B (zh) * | 2019-04-08 | 2022-03-11 | 西北师范大学 | 一种能同步荧光识别铝、铬、铁离子的超分子传感器分子的合成和应用 |
| CN110028456B (zh) * | 2019-04-19 | 2021-02-23 | 齐鲁工业大学 | 一种巴比妥酸衍生物及制备方法与应用 |
| CN112920189B (zh) * | 2021-01-29 | 2021-12-21 | 中国科学院城市环境研究所 | 一种高灵敏汞离子荧光传感材料及其制备方法和应用以及检测溶液中汞离子浓度的方法 |
| CN115650923B (zh) * | 2022-10-02 | 2024-02-27 | 齐鲁工业大学 | 一种基于巴比妥酸的荧光探针及其在检测汞离子中的应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107286102A (zh) * | 2016-03-31 | 2017-10-24 | 新疆大学 | 一种小分子聚集态荧光增强型汞离子探针 |
| CN108586438A (zh) * | 2018-05-23 | 2018-09-28 | 齐鲁工业大学 | 一种一取代五元杂环的巴比妥酸衍生物及其制备方法 |
-
2018
- 2018-12-03 CN CN201811466124.3A patent/CN109369624B/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107286102A (zh) * | 2016-03-31 | 2017-10-24 | 新疆大学 | 一种小分子聚集态荧光增强型汞离子探针 |
| CN108586438A (zh) * | 2018-05-23 | 2018-09-28 | 齐鲁工业大学 | 一种一取代五元杂环的巴比妥酸衍生物及其制备方法 |
Non-Patent Citations (1)
| Title |
|---|
| Synthesis of 5-Arylidene-2,4,6(1H,3H,5H)pyrimidinetrione Derivatives;Prousek, Josef;《Collection of Czechoslovak Chemical Communications》;19931231;第58卷(第12期);第3014页化合物IIb，第3015页实验内容 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109369624A (zh) | 2019-02-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109369624B (zh) | 一种巴比妥酸衍生物及其制备和在荧光识别铁离子和汞离子中的应用 | |
| CN108169189B (zh) | 一种响应二氧化硫/亚硫酸（氢）盐的比率荧光探针 | |
| Han et al. | Colorimetric hydrazine detection and fluorescent hydrogen peroxide imaging by using a multifunctional chemical probe | |
| CN109294558B (zh) | 基于均苯三甲酰氯功能化的主客体组装超分子凝胶及其制备和应用 | |
| CN109187472A (zh) | 一种基于主客体自组装的超分子传感器及其制备和应用 | |
| CN112409292B (zh) | 一种多功能荧光探针及制备方法和应用 | |
| Wu et al. | A novel Near-Infrared fluorescent probe for Zn2+ and CN–double detection based on dicyanoisfluorone derivatives with highly sensitive and selective, and its application in Bioimaging | |
| CN104004514A (zh) | 一种检测三价铋离子的对称双罗丹明荧光探针及制备方法和用途 | |
| CN111808109A (zh) | 一种哒嗪并喹喔啉二胺席夫碱钴离子荧光探针及其制备方法 | |
| Cui et al. | Design and synthesis of a terbium (III) complex-based luminescence probe for time-gated luminescence detection of mercury (II) Ions | |
| CN109053728B (zh) | 基于4-氨基吡啶功能化1,4,5,8-萘四甲酰亚胺超分子有机凝胶及应用 | |
| CN109096369B (zh) | 一种特异性检测铜离子和硫离子的多肽、化学荧光传感器及其制备方法与应用 | |
| CN109608382B (zh) | 一种检测氰根离子和次氯酸的荧光探针及其制备和应用 | |
| CN113234071A (zh) | 三苯胺基甲基吡啶盐及合成方法以及对cn-的识别和生物成像应用 | |
| CN111635354B (zh) | 一种咔唑Schiff碱为识别受体的多离子差异性检测荧光探针 | |
| CN113651828B (zh) | 一种用于检测铬离子和铝离子的近红外荧光探针及其制备方法和应用 | |
| CN108033911B (zh) | 一种二氧化硫/亚硫酸（氢）盐的溶酶体靶向荧光探针 | |
| CN103012375B (zh) | 吡啶基三氮唑甲基取代的吖啶衍生物及其制备方法和应用 | |
| Wang et al. | A new “on-off-on” fluorescent sensor for cascade recognition of Hg2+ and S2− ion in aqueous medium | |
| CN107382901B (zh) | 一种基于苯基噻唑和对氰基联苯酚的荧光传感材料及其制备方法和用途 | |
| CN108918495B (zh) | 基于2-醛基罗丹明类衍生物的分光光度法定量检测氰根离子的方法 | |
| KR101548806B1 (ko) | 신규한 화합물, 이를 이용한 크롬 이온 또는 알루미늄 이온 검출제, 검출방법 및 검출장치 | |
| CN112142764A (zh) | 一种锌配合物及其合成和在荧光识别Fe3+离子的方法 | |
| CN108929673A (zh) | 一种具有aie效应识别铝离子的荧光探针 | |
| CN114213407B (zh) | 一种2-吡啶基噻唑腙类香豆素衍生物化学传感器、制备方法及应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20210730 |