CN106905958A - 一种基于反式七元瓜环的荧光探针、制备方法及应用 - Google Patents
一种基于反式七元瓜环的荧光探针、制备方法及应用 Download PDFInfo
- Publication number
- CN106905958A CN106905958A CN201710170649.1A CN201710170649A CN106905958A CN 106905958 A CN106905958 A CN 106905958A CN 201710170649 A CN201710170649 A CN 201710170649A CN 106905958 A CN106905958 A CN 106905958A
- Authority
- CN
- China
- Prior art keywords
- fluorescence probe
- cucurbit
- uril
- trans
- fluorescence
- 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.)
- Granted
Links
- 239000000523 sample Substances 0.000 title claims abstract description 47
- ZDOBFUIMGBWEAB-XGFHMVPTSA-N cucurbit[7]uril Chemical compound N1([C@H]2[C@H]3N(C1=O)CN1[C@H]4[C@H]5N(C1=O)CN1[C@H]6[C@H]7N(C1=O)CN1[C@H]8[C@H]9N(C1=O)CN1[C@H]%10[C@H]%11N(C1=O)CN([C@@H]1N(C%12=O)CN%11C(=O)N%10CN9C(=O)N8CN7C(=O)N6CN5C(=O)N4CN3C(=O)N2C2)C3=O)CN4C(=O)N5[C@H]6[C@@H]4N2C(=O)N6CN%12[C@@H]1N3C5 ZDOBFUIMGBWEAB-XGFHMVPTSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 238000001338 self-assembly Methods 0.000 claims abstract description 10
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 6
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000001514 detection method Methods 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 13
- 239000012153 distilled water Substances 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 3
- 230000035945 sensitivity Effects 0.000 abstract description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 32
- 239000007864 aqueous solution Substances 0.000 description 13
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical group N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000219112 Cucumis Species 0.000 description 3
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000972773 Aulopiformes Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000000500 calorimetric titration Methods 0.000 description 2
- 238000001506 fluorescence spectroscopy Methods 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- -1 glycosides urea unit Compound Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000004451 qualitative analysis Methods 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 235000019515 salmon Nutrition 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000000832 Ayote Nutrition 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- MDZOTMJVWQCVSB-UHFFFAOYSA-N N=NC=NN.N=NC=NN.[N] Chemical compound N=NC=NN.N=NC=NN.[N] MDZOTMJVWQCVSB-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- MSBXTPRURXJCPF-DQWIULQBSA-N cucurbit[6]uril Chemical compound N1([C@@H]2[C@@H]3N(C1=O)CN1[C@@H]4[C@@H]5N(C1=O)CN1[C@@H]6[C@@H]7N(C1=O)CN1[C@@H]8[C@@H]9N(C1=O)CN([C@H]1N(C%10=O)CN9C(=O)N8CN7C(=O)N6CN5C(=O)N4CN3C(=O)N2C2)C3=O)CN4C(=O)N5[C@@H]6[C@H]4N2C(=O)N6CN%10[C@H]1N3C5 MSBXTPRURXJCPF-DQWIULQBSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 238000007479 molecular analysis Methods 0.000 description 1
- 239000003147 molecular marker Substances 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011897 real-time detection Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000011895 specific detection Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
本发明公开了一种基于反式七元瓜环的荧光探针、制备方法及应用。包括iQ[7]与DASPM合成摩尔比为1:1的自组装络合物，所述的自组装络合物的分子式为C58H61N30O14，结构式为：本发明具有高灵敏度和高选择性识别对苯二甲胺分子的特点。
Description
技术领域
本发明涉及有机合成和分析化学领域，特别是一种基于反式七元瓜环的荧光探针、制备方法及应用。
背景技术
瓜环又名葫芦脲(Cucurbit[n]uril简称Q[n]或CB[n])作为一类新型大环化合物，因其结构貌似南瓜又为环状物而得名，是由苷脲单元通过亚甲基桥联形成的一类新型大环化合物。反式七元瓜环(即iQ[7])存在一个反转的苷脲单元，使得空腔相比较于七元瓜环较小。由于其具有内疏水外亲水空腔及由环绕的羰基氧原子组成的端口，使得瓜环能够通过疏水作用、氢键、离子偶极等非共价键作用键合多种阳离子客体及中性分子形成的超分子自组装结构在分子开关、分子梭、信息存储等方面,以及药物缓释、分子识别等方面都有潜在的应用价值。
分子识别最初是被用来在分子研究生物体系中的化学问题而提出的。分子识别通过变换和易位过程产生催化作用,在生物体系中,是理解酶反应、信息传递和不同介质间物种能量转移现象的信息来源,在分析化学领域则是构成分离、检测和定量测定的基础超分子包结物的形成则是建立在分子识别的基础之上。建立在分子识别基础上的荧光探针技术，通过对特定目标分子、离子的选择性结合，实现识别信息通过相应的荧光信号传导转换为易于检测的光谱信号，从而实现在分子水平上的原位、实时检测，并能提供丰富的光谱信息，在各种离子检测、DNA及蛋白质分子标记、细胞成像、免疫分析等方面发挥着重要作用。但是目前并没有关于反式七元瓜环-荧光体超分子体系作为分子探针的报道。
发明内容
本发明的目的是提供一种基于反式七元瓜环的荧光探针、制备方法及应用。本发明具有高灵敏度和高选择性识别对苯二甲胺分子的特点。
本发明是这样实现的：包括iQ[7]与DASPM合成摩尔比为1:1的自组装络合物，所述的自组装络合物的分子式为C58H61N30O14，结构式为：
前述的基于反式七元瓜环的荧光探针,按下述步骤制备：将iQ[7]和DASPM加入蒸馏水混合，混合后加热到45-55℃反应，反应完全后降温，制得所述的荧光探针的溶液。
前述的基于反式七元瓜环的荧光探针,按下述步骤制备：将iQ[7]与DASPMI按照摩尔比1:1的比例混合，并加入蒸馏水配置成(1.0-2.0)×10-4mol·L-1的混合溶液，在45-55℃搅拌反应2h，冷却至室温制备得到橙红色溶液，即所述的荧光探针的溶液。
前述的基于反式七元瓜环的荧光探针用于对苯二甲胺分子的识别检测。
有益效果
与现有技术相比，本发明用于检测对苯二甲胺的荧光光度定性和定量分析，在水溶液介质条件下，利用荧光发射光谱检测微量对苯二甲胺。上述荧光光度定性和定量分析的荧光光谱的激发波长419nm,最大发射波长582nm.荧光光谱特征为探针加入对苯二甲胺后，最大发射波长582nm处的荧光强度明显降低。由此可知本发明具有操作方法简便，灵敏度高、选择性能优越等特点。
为了进一步验证本发明的荧光探针及该荧光探针的有益效果，发明人做了下述实验：
实验1：iQ[7]与DASPM(即染料分子，化学式为2-[4-(二甲氨基)苯乙烯基]-1-甲基吡啶盐碘化物)的核磁共振实验。实验结果如图2所示：其结果显示客体分子(即染料分子)的苯环以及氮二甲基部分进入到瓜环的空腔内部，而氮甲基吡啶部分裸露在瓜环的空腔外部，形成主客体比为1:1的瓜环/染料荧光探针。
实验2：iQ[7]与DASPM的紫外可见光谱与荧光光谱分析。实验结果如图3所示：其结果显示随着iQ[7]的加入染料分子DASPMI的最大紫外吸收波长从437nm红移到455nm，吸收强度先下降后上升，而随着瓜环的加入DASPMI荧光强度逐渐上升，形成1:1的主客体络合物。
实验3：iQ[7]与DASPM的等温量热滴定。实验结果如图4所示：结合常数为(6.58±0.53)×105M-1，吉布斯自由能-33.21kJ/mol，其中主客体摩尔比为0.981±0.017，由此可知，瓜环与染料分子形成1:1的主客体络合物。
实验4：浓度为2.00×10-5mol·L-1探针的水溶液，加入各种胺类分子后的反应分析。如图5所示，在水溶液中，本发明的荧光探针具有较强的荧光发射，激发波长为419nm，发射波长为582nm，在582nm紫外灯下观察到发射黄色荧光。当加入各种胺类分子的水溶液后，观察到当加入对苯二甲胺溶液时荧光发射强度显著降低，而其他实验胺类分子对检测体系均无明显的响应信号，这表明荧光探针对对苯二甲胺具有识别检测性能。如图6所示，随着对苯二甲胺的加入，探针的荧光强度逐渐下降，直到加入4倍量的对苯二甲胺时，体系的荧光强度趋于平缓。最后通过综合分析染料分子的荧光强度曲线、探针的荧光强度曲线和加入4倍量的对苯二甲胺荧光强度曲线(如图7所示)可得：本发明所述的荧光探针对对苯二甲胺有明显的检测效果。
附图说明
图1为本发明所述的荧光探针的结构式；
图2为2.00×10-4mol·L-1的iQ[7]的氘代水溶液，逐步加入DASPMI的核磁共振谱图；
图3为2.00×10-5mol·L-1的DASPMI的水溶液，逐步加入反式七元瓜环的紫外吸收光谱以及荧光光谱图；
图4为1.00×10-4mol·L-1的iQ[7]的水溶液，逐步加入1.00×10-3mol·L-1的DASPMI的等温量热滴定谱图；
图5为2.00×10-5mol·L-1的荧光探针的水溶液，加入各种胺类分子后的荧光发射光谱图；
图6为2.00×10-5mol·L-1的荧光探针的水溶液，逐渐加入对苯二甲胺分子后的荧光强度变化曲线；
图7为2.00×10-5mol·L-1的DASPMI、荧光探针的水溶液以及加入3倍量的对苯二甲胺后的荧光强度曲线图。
具体实施方式
实施例1。一种基于反式七元瓜环的荧光探针，包括iQ[7]与
DASPM合成摩尔比为1:1的自组装络合物，所述的自组装络合物的分子式为C58H61N30O14，结构式为：
前述的基于反式七元瓜环的荧光探针，按下述步骤制备：将iQ[7]和DASPM加入蒸馏水混合，混合后加热到45-55℃反应，反应完全后降温，制得所述的荧光探针。
前述的基于反式七元瓜环的荧光探针按下述步骤制备：将iQ[7]与DASPMI按照摩尔比1:1的比例混合，并加入蒸馏水配置成(1.0-2.0)×10-4mol·L-1的混合溶液，在45～55℃搅拌反应2h，冷却至室温后得到橙红色液体，即制得所述的荧光探针。
具体地，前述的基于反式七元瓜环的荧光探针下述步骤制备：
a.准确称取6.8mg反式七元瓜环于25ml容量瓶中，用蒸馏水定容后超声震荡，即可得到物质的量浓度为2.00×10-4mol·L-1的A溶液；
b.称取7.3mg DASPM于10ml容量瓶中，用蒸馏水定容后超声震荡，即可得到物质的量浓度为2.00×10-3mol·L-1的B溶液；
c.取2.5mL配置好的B溶液加入到A溶液中，混合均匀，在45～55℃下搅拌反应2h，反应完全后降温，制得所述的2.00×10-4mol·L-1的荧光探针溶液。
前述的基于反式七元瓜环的荧光探针用于对苯二甲胺分子的识别检测。
实施例2。一种基于反式七元瓜环的荧光探针，包括iQ[7]与
DASPM合成摩尔比为1:1的自组装络合物，所述的自组装络合物的分子式为C58H61N30O14，结构式如图1。
前述的基于反式七元瓜环的荧光探针，按下述步骤制备：分别称取反式七元瓜环iQ[7]与DASPMI按照摩尔比1:1的比例，加入蒸馏水，配置2.00×10-4mol·L-1的荧光探针溶液，在45～55℃搅拌反应2h。冷却至室温得到橙红色液体，即所述的荧光探针。
前述的基于反式七元瓜环的荧光探针用于对苯二甲胺分子的识别检测，具体检测如下：
(1)对苯二甲胺的标准溶液：称取对苯二甲胺0.2mmol(27.3mg)配制成100mL水溶液，对苯二甲胺水溶液浓度为2.00×10-3mol·L-1，根据需要用蒸馏水逐级稀释到适宜的浓度；
(2)在10.0mL容量瓶中加入瓜环/染料荧光探针的储备液(2.00×10-4mol·L-1，0.5mL)，各种胺类分子的水溶液(2.00×10-4mol·L-1，1mL)。用蒸馏水溶液稀释至刻度，摇匀，在室温放置2h，移入3cm的石英比色皿进行荧光光谱测定。体系荧光光谱测定的激发和发射波长为419/582nm。
所用试剂为分析纯试剂，试验用水为二次蒸馏水。
所用荧光分光光度计型号为Cary Eclipse荧光分光光度计，美国VARIAN公司制造。
在水溶液中，瓜环/染料荧光探针具有较强的荧光发射，激发波长为419nm，发射波长为582nm，在582nm紫外灯下观察到发射黄色荧光。当加入各种胺类分子的水溶液后，观察到当加入对苯二甲胺溶液时荧光发射强度显著降低，而其他实验胺类分子对检测体系均无明显的响应信号(如图5)。表明荧光探针对对苯二甲胺具有识别检测性能。
荧光探针对苯二甲胺的荧光曲线(如图6)随着对苯二甲胺的加入，探针的荧光强度逐渐下降，直到加入4倍量的对苯二甲胺时，体系的荧光强度趋于平缓。染料分子的荧光强度曲线，探针的荧光强度曲线，与加入4倍量的对苯二甲胺荧光强度曲线(如图7)，说明探针对对苯二甲胺有明显的检测效果。
Claims (4)
1.一种基于反式七元瓜环的荧光探针，其特征在于，包括iQ[7]与DASPM合成摩尔比为1:1的自组装络合物，所述的自组装络合物的分子式为C58H61N30O14，结构式为：
2.一种如权利要求1所述的基于反式七元瓜环的荧光探针的制备方法，其特征在于,按下述步骤制备：将iQ[7]和DASPM加入蒸馏水混合，混合后加热到45-55℃反应，反应完全后降温，制得所述的荧光探针的溶液。
3.如权利要求2所述的基于反式七元瓜环的荧光探针的制备方法，其特征在于：按下述步骤制备：将iQ[7]与DASPMI按照摩尔比1:1的比例混合，并加入蒸馏水配置成(1.0-2.0)×10-4mol·L-1的混合溶液，在45-55℃搅拌反应2h，冷却至室温制备得到橙红色溶液，即所述的荧光探针的溶液。
4.一种如权利要求1所述的基于反式七元瓜环的荧光探针的应用，其特征在于：该荧光探针用于对苯二甲胺分子的识别检测。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710170649.1A CN106905958B (zh) | 2017-03-21 | 2017-03-21 | 一种基于反式七元瓜环的荧光探针、制备方法及应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710170649.1A CN106905958B (zh) | 2017-03-21 | 2017-03-21 | 一种基于反式七元瓜环的荧光探针、制备方法及应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106905958A true CN106905958A (zh) | 2017-06-30 |
| CN106905958B CN106905958B (zh) | 2019-08-02 |
Family
ID=59195139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710170649.1A Expired - Fee Related CN106905958B (zh) | 2017-03-21 | 2017-03-21 | 一种基于反式七元瓜环的荧光探针、制备方法及应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106905958B (zh) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109507163A (zh) * | 2018-12-20 | 2019-03-22 | 贵州大学 | 一种水溶液中h2po4-的检测方法 |
| CN109580567A (zh) * | 2018-12-04 | 2019-04-05 | 贵州大学 | 一种检测水中bf4-、h2po4-和hso4-的方法 |
| CN110208235A (zh) * | 2019-06-26 | 2019-09-06 | 贵州大学 | 一种检测水中农药多果定的荧光探针及其检测方法 |
| CN110527506A (zh) * | 2019-08-27 | 2019-12-03 | 贵州大学 | 一种用于检测苯丙氨酸的高选择性荧光探针及其应用 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1094065A2 (en) * | 1999-10-21 | 2001-04-25 | Pohang University of Science and Technology Foundation | Cucurbituril derivatives, their preparation methods and uses |
| WO2007106144A1 (en) * | 2006-02-28 | 2007-09-20 | University Of Maryland | NOR-SECO-, BIS-NOR-SECO, TRIS-NOR-SECO- AND HIGHER NOR-SECO- CUCURBIT[n]URIL COMPOUNDS |
| CN104151327A (zh) * | 2014-08-25 | 2014-11-19 | 贵州大学 | 反式七元瓜环的合成分离方法 |
| CN104447768A (zh) * | 2013-09-23 | 2015-03-25 | 贵州大学 | 七元瓜环[3]轮烷及其制备方法和应用 |
| CN106290338A (zh) * | 2016-09-10 | 2017-01-04 | 上海大学 | 一种快速检测金刚烷胺含量的方法 |
-
2017
- 2017-03-21 CN CN201710170649.1A patent/CN106905958B/zh not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1094065A2 (en) * | 1999-10-21 | 2001-04-25 | Pohang University of Science and Technology Foundation | Cucurbituril derivatives, their preparation methods and uses |
| WO2007106144A1 (en) * | 2006-02-28 | 2007-09-20 | University Of Maryland | NOR-SECO-, BIS-NOR-SECO, TRIS-NOR-SECO- AND HIGHER NOR-SECO- CUCURBIT[n]URIL COMPOUNDS |
| CN104447768A (zh) * | 2013-09-23 | 2015-03-25 | 贵州大学 | 七元瓜环[3]轮烷及其制备方法和应用 |
| CN104151327A (zh) * | 2014-08-25 | 2014-11-19 | 贵州大学 | 反式七元瓜环的合成分离方法 |
| CN106290338A (zh) * | 2016-09-10 | 2017-01-04 | 上海大学 | 一种快速检测金刚烷胺含量的方法 |
Non-Patent Citations (1)
| Title |
|---|
| ANAMIKA MANNA ET AL.: "Switching of emission of a styryl dye in cucurbit[7]uril: A comprehensive experimental and theoretical study", 《SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109580567A (zh) * | 2018-12-04 | 2019-04-05 | 贵州大学 | 一种检测水中bf4-、h2po4-和hso4-的方法 |
| CN109580567B (zh) * | 2018-12-04 | 2021-05-14 | 贵州大学 | 一种检测水中bf4-、h2po4-和hso4-的方法 |
| CN109507163A (zh) * | 2018-12-20 | 2019-03-22 | 贵州大学 | 一种水溶液中h2po4-的检测方法 |
| CN109507163B (zh) * | 2018-12-20 | 2021-03-23 | 贵州大学 | 一种水溶液中h2po4-的检测方法 |
| CN110208235A (zh) * | 2019-06-26 | 2019-09-06 | 贵州大学 | 一种检测水中农药多果定的荧光探针及其检测方法 |
| CN110208235B (zh) * | 2019-06-26 | 2022-02-01 | 贵州大学 | 一种检测水中农药多果定的荧光探针及其检测方法 |
| CN110527506A (zh) * | 2019-08-27 | 2019-12-03 | 贵州大学 | 一种用于检测苯丙氨酸的高选择性荧光探针及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106905958B (zh) | 2019-08-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106905958B (zh) | 一种基于反式七元瓜环的荧光探针、制备方法及应用 | |
| Sun et al. | Recent advances in developing lanthanide metal–organic frameworks for ratiometric fluorescent sensing | |
| Wang et al. | Rhodamine-based highly sensitive colorimetric off-on fluorescent chemosensor for Hg 2+ in aqueous solution and for live cell imaging | |
| Fereja et al. | A recent review on chemiluminescence reaction, principle and application on pharmaceutical analysis | |
| Wang et al. | A ratiometric fluorescent probe for bisulphite anion, employing intramolecular charge transfer | |
| CN106916591B (zh) | 一种发射白色荧光的碳点及其在检测有机试剂中的应用 | |
| CN107814808B (zh) | 一种近红外反应型双光子荧光探针及其制备方法和应用 | |
| Qu et al. | A fluorescence “switch-on” approach to detect hydrazine in aqueous solution at neutral pH | |
| CN105906643B (zh) | 一种近红外gsh荧光探针的制备方法和应用 | |
| CN104447768A (zh) | 七元瓜环[3]轮烷及其制备方法和应用 | |
| CN107082785A (zh) | 一种检测氰根离子的荧光探针及其合成合应用方法 | |
| Gao et al. | An Aza-Cope mediated fluorescent probe based on aggregation-induced emission for highly selective and sensitive detection of formaldehyde in living cells and tissues | |
| CN105924449A (zh) | 一种检测汞离子反应型荧光素类荧光探针制备与应用 | |
| CN103497121A (zh) | 均苯三甲酰腙系列衍生物的制备及其作为探针分子识别氟离子的应用 | |
| CN108752377B (zh) | 一种检测过氧亚硝基阴离子的荧光探针、合成方法和应用 | |
| CN105038295A (zh) | 一种基于菁染料为骨架的近红外荧光化合物、制备及其应用 | |
| An et al. | Energy transfer chemiluminescence for ratiometric pH imaging | |
| CN106518763B (zh) | 一种选择性比率式检测氰根离子的荧光探针及其合成方法与应用 | |
| CN110229165A (zh) | 上转换荧光探针罗丹明衍生物及其应用 | |
| Lei et al. | A ratiometric fluorescent probe for sensing hydrogen peroxide based on a hemicyanine–naphthol fluorophore | |
| CN105038761A (zh) | 荧光波长可调材料及应用 | |
| CN104448254B (zh) | 一种含卟啉铂配合物磷光共轭聚电解质光电材料及其制备方法和应用 | |
| CN110642882B (zh) | 一种兼具双氧水检测和光动力杀伤癌细胞活性的荧光探针及其制备方法和应用 | |
| CN109652062B (zh) | 一种荧光探针t及其制备和应用 | |
| CN107417681A (zh) | 一种含有香豆素‑噻二唑基席夫碱荧光探针化合物及其制备方法和用途 |
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: 20190802 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |