CN109265473B - 一种含混合配体锌(ⅱ)金属有机配合物及其制备方法和应用 - Google Patents
一种含混合配体锌(ⅱ)金属有机配合物及其制备方法和应用 Download PDFInfo
- Publication number
- CN109265473B CN109265473B CN201811433191.5A CN201811433191A CN109265473B CN 109265473 B CN109265473 B CN 109265473B CN 201811433191 A CN201811433191 A CN 201811433191A CN 109265473 B CN109265473 B CN 109265473B
- Authority
- CN
- China
- Prior art keywords
- complex
- biquinoline
- single crystal
- zinc
- nitrobenzene
- 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.)
- Active
Links
- 239000003446 ligand Substances 0.000 title abstract description 12
- 229910052751 metal Inorganic materials 0.000 title abstract description 7
- 239000002184 metal Substances 0.000 title abstract description 7
- 238000002360 preparation method Methods 0.000 title abstract description 7
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 title description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000013078 crystal Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000008367 deionised water Substances 0.000 claims abstract description 9
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 9
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 claims abstract description 8
- WPTCSQBWLUUYDV-UHFFFAOYSA-N 2-quinolin-2-ylquinoline Chemical compound C1=CC=CC2=NC(C3=NC4=CC=CC=C4C=C3)=CC=C21 WPTCSQBWLUUYDV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 6
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000012065 filter cake Substances 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 238000004729 solvothermal method Methods 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- 239000007795 chemical reaction product Substances 0.000 claims abstract 2
- -1 5-amino isophthalic acid zinc-biquinoline metal complex Chemical class 0.000 claims description 11
- 238000002447 crystallographic data Methods 0.000 claims description 4
- 238000007670 refining Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000011701 zinc Substances 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 229910052725 zinc Inorganic materials 0.000 abstract description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007900 aqueous suspension Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000725 suspension Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 5
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000010886 Peripheral nerve injury Diseases 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229920001795 coordination polymer Polymers 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 239000002957 persistent organic pollutant Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- 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
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- 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
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
本发明公开了一种含混合配体锌(Ⅱ)金属有机配合物及其制备方法和应用。将六水合硝酸锌、叠氮酸钠、5‑氨基间苯二甲酸和2,2’‑联喹啉在二次去离子水中进行溶剂热反应。反应产物过滤，去离子水洗涤滤饼，得到化学式为C52H34N6O8Zn2的黄色块状配合物单晶。配合物通过5‑氨基间苯二甲酸根桥联形成一维螺旋链状结构，再由分子间氢键和π···π芳香环堆积构成三维超分子结构。该配合物/水的悬浮液在406纳米处具有很强的荧光发射，在加入硝基苯后荧光迅速猝灭，可作为荧光探针检测水体中的硝基苯。
Description
技术领域
本发明属于有机合成领域，涉及一种联喹啉类锌金属有机配合物及其制备方法，和该配合物在荧光检测方面的应用。
背景技术
硝基苯是一种重要的化工原料，在医药、染料、炸药等行业被广泛应用。硝基苯对人体危害性极强，人们长期接触硝基苯的水体，会造成肝脏、血液、皮肤等器官的病变以及周围神经损伤，属我国首批水中优先控制污染物黑名单68个中的一种。尽管检测硝基苯的方法多种多样，如化学分析法，色谱法、电化学方法、光谱分析法等，但这些方法均存在着费用高、分析时间长、可能造成二次污染等缺点，故寻找一种高效、快速、安全地检测水体中硝基苯的方法是目前该领域研究的一个热点。近年来，使用荧光探针检测化学污染物的方法以其灵敏度高、费用低、易操作和响应时间短等优点吸引了人们的广泛关注。在各种荧光探针中，金属有机配合物以其结构多变性，性能可调控性和易制备、光敏性好等特点成为首选，在检测有机污染物和金属离子方面具有巨大的潜力。
发明内容
本发明的第一个目的是提供一种含混合配体锌(Ⅱ)金属有机配合物，即5-氨基间苯二甲酸锌-联喹啉金属配合物。该配合物以联喹啉和5-氨基间苯二甲酸根为配体，形成了一维螺旋链状配位聚合物，通过配体间的π···π相互作用，构成二维层状结构，再由氢键和芳香环堆积构成三维超分子结构。
本发明所涉及的5-氨基间苯二甲酸锌-联喹啉金属配合物的化学式为Zn2(biq)2(5-aip)2，其中biq为联喹啉，5-aip为5-氨基间苯二甲酸根。
该配合物的晶体属单斜晶系，空间群为P21/c。晶胞参数为：
α＝90.00°，β＝119.05(10)°，γ＝90.00°。配合物晶体最小不对称结构单元中包含两个Zn2+，两个biq配体、两个5-aip阴离子。两个Zn2+配位模式不同，其中Zn1原子分别与同一个biq配体的两个N原子、来源于两个不同配位形式的5-aip配体的两个O原子配位，形成四面体构型；Zn2原子则与另一个biq配体的两个N原子和来自两个不同配位形式的5-aip配体的三个O原子配位，形成畸变的四方锥配位构型。Zn1-N键长为2.059(2)和
Zn1-O键长为1.893(2)和
N/O-Zn1-N/O键角在81.10(10)～128.23(10)°之间；Zn2-N键长为2.095(3)和
Zn2-O键长为2.388(2)、2.002(2)和
N/O-Zn2-N/O键角在59.00(8)～159.91(9)°之间。每个配位的5-aip配体桥联两个Zn(Ⅱ)原子形成一维螺旋链，同时，通过分子间弱的氢键和π···π芳香环堆积构成三维超分子结构。
本发明的第二个目的是提供一种5-氨基间苯二甲酸锌-联喹啉金属配合物的制备方法。
为达到上述目的，本发明5-氨基间苯二甲酸锌-联喹啉金属配合物的制备方法是：将六水合硝酸锌、叠氮酸钠、5-氨基间苯二甲酸和2,2’-联喹啉在二次去离子水中进行溶剂热反应。其中六水合硝酸锌、叠氮酸钠、5-氨基间苯二甲酸、2,2’-联喹啉的摩尔比为2:4:1:1。反应介质为二次去离子水，叠氮酸钠充当碱，在150-180℃下反应3天，随后降至室温，得黄色块状晶体，过滤，去离子水洗涤滤饼，得目标配合物单晶。
本发明的第三个目的在于提供一种5-氨基间苯二甲酸锌-联喹啉金属配合物作为荧光探针检测水体中低浓度的硝基苯。
为达到上述目的，将5-氨基间苯二甲酸锌-联喹啉金属配合物加入到水溶剂中，超声波分散，配制成悬浊液，测定其荧光发射光谱。再将上述悬浊液注入到比色皿中，逐次向内加入纯硝基苯溶剂，分别测其悬浊液荧光发射光谱。随着硝基苯浓度增加，配合物悬浊液的荧光发射强度迅速减弱，当硝基苯加入至一定量时，该悬浮液基本无荧光发射。据此，可以检测水体中的硝基苯。
附图说明
图1是本发明5-氨基间苯二甲酸锌-联喹啉金属配合物的晶体不对称结构图；
图2是本发明5-氨基间苯二甲酸锌-联喹啉金属配合物一维链状结构图；
图3是本发明浓度为1.5×10-6mol/L的5-氨基间苯二甲酸锌-联喹啉金属配合物/水的悬浊液中滴加硝基苯的荧光发射光谱图，其中箭头所指的数据为加入的硝基苯的体积量。
具体实施方式
下面结合具体实施实例进一步阐述本发明。
实施例：将Zn(NO3)2·6H2O(59.2mg，0.2mmol)、NaN3(26.0mg，0.4mmol)、5-氨基间苯二甲酸(18.1mg，0.1mmol)，2,2’-联喹啉(25.63mg，0.1mmol)及15mL的二次去离子水作溶剂加入到25mL的高压反应釜内，加热至180℃，维持该温度反应3天。待其自行冷却至室温，得到黄色块状晶体，过滤，去离子水洗涤滤饼，得目标配合物单晶。基于Zn(NO3)2·6H2O计算产率约为51％。
本发明所述的5-氨基间苯二甲酸锌-联喹啉金属配合物进一步表征，其过程如下：
1、所述的配合物晶体结构测定
选取0.180mm×0.160mm×0.150mm大小的单晶，于293K下在Bruker Smart APEXII CCD单晶衍射仪上，以经石墨单色化的Mo-kα射线
为入射辐射，
扫描方式收集X-射线单晶衍射数据，采用最小二乘法精修晶胞参数，SHELXL-97直接法解析晶体结构，所有非氢原子用全矩阵最小二乘法进行各向异性精修，H原子位置理论模式计算确定。晶体衍射数据收集和结构精修的部分参数见表1，晶体结构如图1～2所示。
2、所述的配合物作为荧光探针检测水体中低浓度的硝基苯。
取3.0mg的5-氨基间苯二甲酸锌-联喹啉金属配合物加入到水溶剂中，超声波分散，配制成1.5×10-6mol/L的悬浊液。将上述悬浊液注入到4.5mL的比色皿中，用Hitachi F-4500荧光光谱仪测定荧光发射光谱。再逐次向内加入0.1μL纯硝基苯溶剂，分别测其悬浊液荧光发射光谱。随着硝基苯浓度增加，配合物悬浊液的荧光强度迅速减弱，当硝基苯加入量为0.5μL即水溶液中硝基苯的浓度为0.000133g/mL时，该悬浮液基本无荧光发射(图3所示)。据此，可检测水体中微量的硝基苯。
表1本发明5-氨基间苯二甲酸锌-联喹啉金属配合物的晶体学数据
Claims (4)
1.5-氨基间苯二甲酸锌-联喹啉金属配合物单晶，其特征在于该单晶的分子式为Zn2(biq)2(5-aip)2，其中biq为2,2’-联喹啉，5-aip为5-氨基间苯二甲酸根；晶体结构采用Bruker Smart Apex IICCD单晶衍射仪测定，以石墨单色化的Mokα射线
为入射辐射，ω-2θ扫描方式收集室温X-射线单晶衍射数据，最小二乘法精修晶胞参数，SHELXL-97直接法解得晶体数据：
2.一种如权利要求1所述的配合物单晶的制备方法，其特征在于：将六水合硝酸锌、叠氮酸钠、5-氨基间苯二甲酸和2,2’-联喹啉在二次去离子水中进行溶剂热反应，反应产物过滤，去离子水洗涤滤饼，得目标配合物单晶，其中叠氮酸钠起碱的作用。
3.一种如权利要求2所述的配合物单晶的制备方法，其特征在于：六水合硝酸锌、叠氮酸钠、5-氨基间苯二甲酸和2,2’-联喹啉的摩尔比为2∶4∶1∶1，进行溶剂热反应的温度为180℃，维持该温度反应3天。
4.一种如权利要求1所述的配合物单晶作为荧光探针检测水体中的硝基苯。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811433191.5A CN109265473B (zh) | 2018-11-28 | 2018-11-28 | 一种含混合配体锌(ⅱ)金属有机配合物及其制备方法和应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811433191.5A CN109265473B (zh) | 2018-11-28 | 2018-11-28 | 一种含混合配体锌(ⅱ)金属有机配合物及其制备方法和应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109265473A CN109265473A (zh) | 2019-01-25 |
| CN109265473B true CN109265473B (zh) | 2020-10-23 |
Family
ID=65186259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811433191.5A Active CN109265473B (zh) | 2018-11-28 | 2018-11-28 | 一种含混合配体锌(ⅱ)金属有机配合物及其制备方法和应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109265473B (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111057077B (zh) * | 2019-12-31 | 2023-04-07 | 安庆师范大学 | 一种磺酸类锌金属有机配合物及其应用 |
| CN111533689B (zh) * | 2020-05-28 | 2023-08-18 | 烟台大学 | 一种2,2’-联喹啉类化合物及其一锅制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080206890A1 (en) * | 2006-07-31 | 2008-08-28 | Wisconsin Alumni Research Foundation | Bis(2,9-di-tert-butyl-1,10-phenanthroline)copper(i) complexes, methods of synthesis, and uses therof |
| CN103665013A (zh) * | 2013-12-04 | 2014-03-26 | 天津工业大学 | 5-氨基间苯二甲酸过渡金属锌配合物及其制备方法 |
| CN103864825A (zh) * | 2014-01-21 | 2014-06-18 | 安庆师范学院 | 一种基于混合配体的锌配合物及其制备方法 |
| CN104447377A (zh) * | 2014-11-14 | 2015-03-25 | 天津工业大学 | 一种发光金属有机框架材料在硝基芳烃类污染物检测中的应用 |
-
2018
- 2018-11-28 CN CN201811433191.5A patent/CN109265473B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN109265473A (zh) | 2019-01-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Liu et al. | Multi-functional fluorescent responses of cobalt complexes derived from functionalized amide-bridged ligand | |
| CN108998007B (zh) | 一种稀土金属有机框架材料的制备方法 | |
| CN104370952A (zh) | 一种基于有机配体的多功能锌配合物及其应用 | |
| CN108384018B (zh) | 一种mof配合物及其合成和在荧光识别铁离子的应用 | |
| CN109265473B (zh) | 一种含混合配体锌(ⅱ)金属有机配合物及其制备方法和应用 | |
| CN106866989B (zh) | 一种具有选择性探测Fe3+离子的发光晶体材料的制备方法 | |
| CN107011367A (zh) | 一种具有选择性探测重铬酸根离子的发光晶体材料的制备 | |
| Quan et al. | Eu (III) functionalized crystalline polyimide hydrogel film as a multifunctional platform for consecutive sensing of spermine and copper ions | |
| CN107573258B (zh) | 一种检测铝离子和锌离子的荧光探针及制备方法与应用 | |
| Li et al. | One-pot synthesis of 2, 2'-dipicolylamine derived highly photoluminescent nitrogen-doped carbon quantum dots for Fe3+ detection and fingermark detection | |
| CN108484927A (zh) | 一种对硝基苯具有选择性荧光识别的锌基金属有机框架及其制备方法 | |
| CN103421030B (zh) | 用作镉离子荧光探针的二元芳香酸铈配合物及其制备方法 | |
| CN106496253B (zh) | 一种噻酚基有机配体的多功能锌/镉配合物及其应用 | |
| CN109384804B (zh) | 一种六亚甲基四胺配体的铜碘配合物、其制备方法及应用 | |
| CN110217825A (zh) | 一种高核金属锰簇的制备方法 | |
| Wang et al. | Three Zn (II) coordination polymers constructed with a new amide-thiophene-derived bis-pyridyl ligand as ultrasensitive luminescent sensors for Hg (II) and purines | |
| CN101735798A (zh) | 对丙酮有传感功能的稀土有机骨架材料及制备方法与应用 | |
| CN111057077B (zh) | 一种磺酸类锌金属有机配合物及其应用 | |
| CN115181279B (zh) | 用于检测人体的生物标志物3-硝基酪氨酸的荧光型金属-有机框架材料及其应用 | |
| CN114920762B (zh) | 一种有机杂化碘化亚铜双响应荧光探针材料及其制备方法 | |
| CN105669709B (zh) | 检测镉离子的含铜化合物及其制备方法和应用 | |
| CN103980884A (zh) | Al3+荧光传感器、合成方法及应用 | |
| CN109912633B (zh) | Eu-配合物荧光探针及其制备方法和应用 | |
| CN108659821A (zh) | 3,3′,5,5′-氧化偶氮苯四甲酸钴(ii)金属配位聚合物及其合成方法和应用 | |
| CN116135911A (zh) | 一种噻菌灵类镉金属有机配合物及其制备方法与应用 |
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 | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20221123 Address after: No. 2, West Ring Road, High tech Zone, Anqing City, Anhui Province 246005 Patentee after: ZHONGXI NEW MATERIAL (ANHUI) CO.,LTD. Address before: 246133 1318 Jixian North Road, Anqing, Anhui Patentee before: ANQING NORMAL University |