CN109467712A - Metal organic framework MOF-Zn fluorescent sensor material and preparation method and application thereof - Google Patents
Metal organic framework MOF-Zn fluorescent sensor material and preparation method and application thereof Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 239000000463 material Substances 0.000 title claims abstract description 17
- 239000012621 metal-organic framework Substances 0.000 title claims abstract description 16
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 16
- 239000003446 ligand Substances 0.000 claims abstract description 13
- 229960005070 ascorbic acid Drugs 0.000 claims abstract description 8
- 235000010323 ascorbic acid Nutrition 0.000 claims abstract description 8
- 239000011668 ascorbic acid Substances 0.000 claims abstract description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 99
- 239000011701 zinc Substances 0.000 claims description 79
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 57
- 239000000243 solution Substances 0.000 claims description 57
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000000126 substance Substances 0.000 claims description 24
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 22
- 238000001514 detection method Methods 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 150000002460 imidazoles Chemical class 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 14
- 150000003751 zinc Chemical class 0.000 claims description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
- 239000004202 carbamide Substances 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 11
- 238000007654 immersion Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- 239000005457 ice water Substances 0.000 claims description 10
- 239000011259 mixed solution Substances 0.000 claims description 10
- 238000000967 suction filtration Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 7
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 7
- 239000011686 zinc sulphate Substances 0.000 claims description 7
- 239000000523 sample Substances 0.000 claims description 6
- 238000005303 weighing Methods 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000001967 indiganyl group Chemical group [H][In]([H])[*] 0.000 claims description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 3
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical class [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 abstract description 2
- VWSRHOIRMGHAPR-UHFFFAOYSA-N 2-methyl-1-[4-(2-methylimidazol-1-yl)butyl]imidazole Chemical compound CC1=NC=CN1CCCCN1C(C)=NC=C1 VWSRHOIRMGHAPR-UHFFFAOYSA-N 0.000 abstract 1
- 235000001014 amino acid Nutrition 0.000 description 10
- 150000001413 amino acids Chemical class 0.000 description 10
- 238000010791 quenching Methods 0.000 description 9
- 239000012491 analyte Substances 0.000 description 7
- 230000000171 quenching effect Effects 0.000 description 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 6
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 3
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 3
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- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 3
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- 238000005259 measurement Methods 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- GDSOZVZXVXTJMI-SNAWJCMRSA-N (e)-1-methylbut-1-ene-1,2,4-tricarboxylic acid Chemical compound OC(=O)C(/C)=C(C(O)=O)\CCC(O)=O GDSOZVZXVXTJMI-SNAWJCMRSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
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- 238000013329 compounding Methods 0.000 description 2
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- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
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- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- 206010047623 Vitamin C deficiency Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
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- 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
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- 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"
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- C09K2211/18—Metal complexes
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- 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
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Abstract
The invention discloses a metal organic framework MOF-Zn fluorescent sensor material and a preparation method and application thereof. Using high purity bbi ═ 1, 4-bis (2-methylimidazol-1-yl) butane as the primary ligand, and Zn2+The salt is used as a metal node to construct a novel MOF-Zn material with stable fluorescence property, and can be used for detecting ascorbic acid with high selectivity, high sensitivity and high stability.
Description
Technical field
The invention belongs to analytical chemistry field, metal-organic framework materials MOF-Zn fluorescent optical sensor and preparation method thereof and
Using more particularly to a kind of metal organic framework MOF-Zn fluorescent sensor material and its preparation method and application, utilize high-purity
Bis- (2-methylimidazole -1- base) butane of bbi=1,4- use Zn as major ligand2+Salt constructs newly as metal node
Have and stablize the MOF-Zn material of photoluminescent property, can be used for highly selective, highly sensitive, high stability detection ascorbic acid.
Background technique
With the development of society and the improvement of people's living standards, requirement of the people to quality of life is also higher and higher, resists
Bad hematic acid (AA) and human health are closely related.The shortage of AA will lead to scurvy, anaemia and immunity degradation in human body.But
It is that Excess free enthalpy AA can also cause diarrhea, the diseases such as stone in urinary system.The intracorporal AA of people is mainly from food, fruit and beverage
Intake.The balance of the intake content of AA can generate subtle influence to human health.Therefore, it develops a kind of highly sensitive
Property detection AA method be very important.
Up to the present, several method has been developed for sensitive and specific measurement AA, including chromatography, capillary be electric
Swimming method (CE), titration, electrochemical process (EC), spectrophotometry and biological enzyme.Such as have by using PCN-333 (aluminium) metal
Machine skeleton (MOFs) be used as catalyst, be prepared for AA electrochemistry ratio biosensor, using electrochemical redox signal into
Row detection, to the detection of AA be limited to 4.6 ± 0.1 μM (Li Wang, Coucong Gong, Yuan Shen, Wenhui Ye,
Mengli Xu,Yonghai Song,A novel ratiometric electrochemical biosensor for
Sensitive detection of ascorbic acid), however, most of in these technologies be it is time-consuming, it is expensive and
And professional technician is needed to operate.In recent years, scientific worker, which begins one's study, uses MOFs to detect AA as fluorescence probe.Such as
AA is detected using the metal-organic framework materials MIL-88 of solvent-thermal method preparation, 1.03 × 10 are limited to the detection of AA-6M(Cunji
Gao,Hongmei Zhu,Jia Chen,Hongdeng Qiu,Facile synthesis of enzyme functional
metal-organic framework for colorimetric detecting H2O2and ascorbic acid).But it should
Method detects limit for height, costs dearly, cannot accomplish the accurate detection to AA, be very limited in practical application.
Summary of the invention
Objects of the present invention are to provide a kind of metal organic framework MOF-Zn fluorescence sense in view of the deficiencies of the prior art
Equipment material and its preparation method and application reduces the detection to AA and limits, can respond in a short time, and can be in pH range
Sensitivity detection carried out to AA in the case where relatively wide and in the presence of different aminoacids, detection limit is down to 1.704ppb.
Technical scheme is as follows:
A kind of preparation method of metal organic framework MOF-Zn fluorescent sensor material, the preparation method is as follows:
The preparation of BBi ligand: a certain amount of imidazoles, NaOH, KOH, Ca (OH) are weighed2One of or several alkali and
CH4N2O is dissolved in H2O, DMA, DMSO, DMF, C2H5OH, CH3In the combination solution of OH one or several kinds, it is thoroughly mixed, in oil
1.5~12h is reacted in bath at 50~70 DEG C, then weighs a certain amount of 1,1-C4H8Cl2, 1,2-C4H8Cl2, 1,3-C4H8Cl2, 1,
4-C4H8Cl2, 2,2-C4H8Cl2And 2,3-C4H8Cl2One or several kinds of combinations, be added in above-mentioned solution several times, continue 5~8h
Afterwards, solution immersion is contained into H2O,DMA,DMSO,DMF,C2H5OH,CH3In the ice water mixed solution of OH one or more combination, one is stood
At night, a large amount of product as white needles are obtained, suction filtration obtains white needle-like crystals, is put into drying for standby in vacuum oven.
Hydro-thermal method prepares MOF-Zn: weighing BBi, phthalic acid, phthalic acid and Zn (NO3)2, (CH3COO)2Zn,
ZnSO4One of zinc salt in C2H5OH, CH3OH, H2It is filled in the combination solvent of O, DMF, DMA, DMSO one or more substance
Divide and be mixed, be subsequently placed in polytetrafluoroethyllining lining, is reacted in 24~48h at 60~90 DEG C, obtain colorless and transparent monocrystalline.
The preparation method, imidazoles, NaOH, KOH, Ca (OH)2One of or several alkali, CH4N2O three's molar ratio
For 1:1:1.
The preparation method, 1,1-C4H8Cl2, 1,2-C4H8Cl2, 1,3-C4H8Cl2, Isosorbide-5-Nitrae-C4H8Cl2, 2,2-C4H8Cl2
And 2,3-C4H8Cl2One or several kinds of combined moles be imidazoles, NaOH, KOH, Ca (OH)2It is one of or several
Alkali, CH4N22 times of the sum of O three's mole.
The preparation method, BBi, phthalic acid, phthalic acid, Zn (NO3)2, (CH3COO)2Zn, ZnSO4's
One of zinc salt, four mass ratioes are 1:1:1:2.
The preparation method, first synthetic ligands bbi: a certain amount of imidazoles 3.4g, NaOH (2.0g and urea are weighed
3.0g is dissolved in H2O, DMA, DMSO, DMF, C2H5OH, CH3In the combination solution 10mL of OH one or several kinds, it is sufficiently stirred mixed
It closes, reacts 1.5~12h at 50~70 DEG C in oil bath pan, then weigh the 1,1-C of 0.075mol4H8Cl2, 1,2-C4H8Cl2,
1,3-C4H8Cl2, Isosorbide-5-Nitrae-C4H8Cl2, 2,2-C4H8Cl2And 2,3-C4H8Cl2One or several kinds of combinations be added several times
It states in solution, after continuing 5~8h, solution immersion is contained into 500mLH2O, DMA, DMSO, DMF, C2H5OH, CH3OH is a kind of or several
In the combined ice water mixed solution of kind, a night is stood, obtains a large amount of product as white needles, suction filtration obtains white needle-like crystals, puts
Enter drying for standby in vacuum oven；
Weigh BBi15mg, phthalic acid 15mg, phthalic acid 15mg and Zn (NO3)2, (CH3COO)2Zn, ZnSO4's
One of zinc salt 30mg is in C2H5OH, CH3OH, H2In the combination solution of O, DMF, DMA, DMSO one or more substance sufficiently
It is mixed, is subsequently placed in polytetrafluoroethyllining lining, reacted in 24~48h at 60~90 DEG C, obtain colorless and transparent monocrystalline.
The preparation method, first synthetic ligands bbi: imidazoles 6.8g, NaOH 4.0g and urea 6.0g are weighed and is dissolved in
H2O, DMA, DMSO, DMF, C2H5OH, CH3It in the combination solution 10mL of OH one or several kinds, is thoroughly mixed, 50 in oil bath pan
1.5~12h is reacted at~70 DEG C, then weighs the 1,1-C of 0.15mol4H8Cl2, 1,2-C4H8Cl2, 1,3-C4H8Cl2, Isosorbide-5-Nitrae-C4H8Cl2,
2,2-C4H8Cl2And 2,3-C4H8Cl2One or several kinds of combinations be added in above-mentioned solution several times, will be molten after continuing 5~8h
Liquid immersion contains 500mLH2O,DMA,DMSO,DMF,C2H5OH,CH3In the ice water mixed solution of OH one or more combination, one is stood
At night, a large amount of product as white needles are obtained, suction filtration obtains white needle-like crystals, is put into drying for standby in vacuum oven；
Weigh BBi26mg, phthalic acid 26mg, phthalic acid 26mg and Zn (NO3)2, (CH3COO)2Zn, Zn (SO4)
One of zinc salt 52mg in C2H5OH, CH3OH, H2It is filled in the combination solution of O, DMF, DMA, DMSO one or more substance
Divide and be mixed, be subsequently placed in polytetrafluoroethyllining lining, is reacted in 24~48h at 60~90 DEG C, obtain colorless and transparent monocrystalline.
The preparation method, first synthetic ligands bbi: imidazoles 7.8g, NaOH 5.1g and urea 7.6g are weighed and is dissolved in
H2O, DMA, DMSO, DMF, C2H5OH, CH3In the combination solution 10mL of OH one or several kinds, it is thoroughly mixed, in oil bath
1.5~12h is reacted in pot at 50~70 DEG C, then weighs the 1,1-C of 0.165mol4H8Cl2, 1,2-C4H8Cl2, 1,3-
C4H8Cl2, Isosorbide-5-Nitrae-C4H8Cl2, 2,2-C4H8Cl2And 2,3-C4H8Cl2One or several kinds of combinations be added several times it is above-mentioned molten
In liquid, after continuing 5~8h, solution immersion is contained into 500mLH2O,DMA,DMSO,DMF,C2H5OH,CH3OH one or more group
In the ice water mixed solution of conjunction, a night is stood, obtains a large amount of product as white needles, suction filtration obtains white needle-like crystals, is put into true
Drying for standby in empty drying box；
Weigh BBi 45mg, phthalic acid 45mg, phthalic acid 45mg and Zn (NO3)2, (CH3COO)2Zn, Zn
(SO4) one of zinc salt 90mg in C2H5OH, CH3OH, H2In the combination solution of O, DMF, DMA, DMSO one or more substance
It is sufficiently mixed stirring, is subsequently placed in polytetrafluoroethyllining lining, is reacted in 24~48h at 60~90 DEG C, obtains colorless and transparent monocrystalline.
The metal organic framework MOF-Zn fluorescent sensor material prepared according to any the method.
Application of the metal organic framework MOF-Zn fluorescent sensor material in detection ascorbic acid, utilizes MOF-
ZnMOF-Zn fluorescent sensor material is detected as fluorescence probe Ascorbic Acid.
In order to assess the sensitivity of MOF-Zn, quantitative fluorescence titration experiments have been carried out.With the increase of AA concentration, MOF-Zn solution
Fluorescence intensity decrease be intended to quench.When the concentration of AA increases to 0.01M from 0M, the fluorescence intensity of MOF-Zn solution is dull and anxious
Play decline.This shows that MOF-Zn can be highly sensitive to AA as fluorescence probe.It can be quantified by Stern-Volmer (SV) equation
It explains fluorescent quenching efficiency, detection limit: wherein I can also be calculated0Fluorescence intensity before being analyte, I are glimmering after analyte
Luminous intensity, Ksv are quenching constant (M-1), [Q] is the molar concentration of analyte.It is almost sudden when AA concentration increases to 0.071mM
It goes out.The standard deviation (σ) of duplicate measurements three times based on blank solution fluorescence intensity, detection limit (3 σ/Ksv) are calculated as 1.704ppb.
MOF-Zn solution fluorescence intensity in pH=4~11 keeps stablizing, and the MOF-Zn under different pH is taken to measure its XRD,
Its diffraction maximum can be obtained to be consistent with former MOF-Zn substantially, illustrate that crystal form keeps good.
The substance solutions such as 200 μ L amino acid are added into MOF-Zn solution, then 40 μ LAA are added thereto, so that its
There is also the substances such as other amino acid simultaneously in the case where there are AA.The substances such as all amino acid is glimmering after addition compounding substances (Y+AA)
Luminous intensity is all quenched, and illustrates that the identification substances such as AA and other amino acid of the probe property of can choose do not interfere with the detection to AA.
The invention has the following advantages that
1, analyte can be detected in water；
2, other method detection limits reported in the literature that compare are lower；
3, under condition of different pH and under the interference of the substances such as other amino acid, the effect of detection is not still influenced.
Detailed description of the invention
Fig. 1 is the microstructure of MOF-Zn；
Fig. 2 is (a) MOF-Zn asymmetric cell；(b) coordination structure of Zn (II)；(c) chemical structure of MOF-Zn；(d)
The 2D planar structure of MOF-Zn；
Fig. 3 is the topological structure of MOF-Zn；
Fig. 4 is the fluorescent quenching figure that the substances such as different aminoacids and AA are added into MOF-Zn solution；
Fig. 5 is standard curve (Stern-Volmer curve) of the AA to MOF-Zn fluorescent quenching；
Fig. 6 beWhen, the XRD (A) and fluorescence intensity figure (B) of MOF-Zn；
Fig. 7 is when the substances such as other amino acid and AA are existed simultaneously to MOF-Zn fluorescent quenching histogram；
The ultra-violet absorption spectrum (A) and fluorescence emission spectrum (B) that Fig. 8 is MOF-Zn of the present invention；
Fig. 9 is that titration experiments are quenched to MOF-Zn in AA of the present invention；
Figure 10 is process flow chart of the invention；
Specific embodiment
Below in conjunction with specific embodiment, the present invention is described in detail.
The present invention with L-Phe, Urea, β-Ala, L-Asp, DL-Pro, L-Val, L-Glu, Arg, Gly, L-Pyr, Suc,
LAC, CTS, D-Glc, MEL, CA, L-Lys, L-His, L-Leu, L-Met, L-Ser, L-Thr, AA, by synthesized MOF-Zn
Solution carries out selective enumeration method to AA.
The structural formula and abbreviated list of each amino acid of table 1 and other substances
Embodiment 1:
Synthetic ligands bbi first: a certain amount of imidazoles (3.4g, M are weighedImidazoles=68.1g/mol), NaOH (2.0g, MNaOH
=40g/mol) and urea (3.0g, MCH4N2O=60g/mol) it is dissolved in H2O, DMA, DMSO, DMF, C2H5OH, CH3OH etc. it is a kind of or
It in several combination solution of person (10mL), is thoroughly mixed, reacts 1.5~12h at 50~70 DEG C in oil bath pan, then claim
Take the 1,1-C of 0.075mol4H8Cl2, 1,2-C4H8Cl2, 1,3-C4H8Cl2, Isosorbide-5-Nitrae-C4H8Cl2, 2,2-C4H8Cl2And 2,3-
C4H8Cl2One or several kinds of combinations be added in above-mentioned solution several times, after continuing 5~8h, solution immersion is contained
500mLH2O, DMA, DMSO, DMF, C2H5OH, CH3In the ice water mixed solution of the one or more combinations such as OH, a night is stood, is obtained
To a large amount of product as white needles, suction filtration obtains white needle-like crystals, is put into drying for standby in vacuum oven.
It weighs a certain amount of BBi (15mg), phthalic acid (15mg), phthalic acid (15mg) and Zn (NO3)2,
(CH3COO)2Zn, ZnSO4One of zinc salt (30mg) according to the mass ratio of 1:1:1:2 in C2H5OH, CH3OH, H2O, DMF,
It is sufficiently mixed stirring in the combination solution of the one or more substance such as DMA, DMSO, is subsequently placed in polytetrafluoroethyllining lining,
It is reacted in 24~48h at 60~90 DEG C, obtains colorless and transparent monocrystalline.Fig. 1 is obtained MOF-Zn microstructure.
20mg monocrystalline is finally added to 5mLDMSO, DMF, DMA, C2H5OH, H2O, CH3The combination of OH one or more is molten
Ultrasonic disperse in the centrifuge tube of liquid, then configures 10-2The AA solution of M.With liquid-transfering gun take the MOF-Zn solution of 100~150 μ L in
It is settled to 5mL in centrifuge tube, a certain amount of detection solution is then added.Fig. 8 is the UV-vis absorption spectrum (A) of MOF-Zn solution
With fluorescence spectrum (B).
Embodiment 2:
Synthetic ligands bbi first: weighing a certain amount of imidazoles (6.8g), and NaOH (4.0g) and urea (6.0g) are dissolved in H2O,
DMA, DMSO, DMF, C2H5OH, CH3In the combination solution (10mL) of the one or several kinds such as OH, it is thoroughly mixed, in oil bath
1.5~12h is reacted in pot at 50~70 DEG C, then weighs the 1,1-C of 0.15mol4H8Cl2, 1,2-C4H8Cl2, 1,3-C4H8Cl2,
1,4-C4H8Cl2, 2,2-C4H8Cl2And 2,3-C4H8Cl2One or several kinds of combinations be added in above-mentioned solution several times, hold
After continuous 5~8h, solution immersion is contained into 500mLH2O,DMA,DMSO,DMF,C2H5OH,CH3The ice of the one or more combinations such as OH
In water mixed solution, a night is stood, obtains a large amount of product as white needles, suction filtration obtains white needle-like crystals, is put into vacuum drying
Drying for standby in case.
It weighs a certain amount of BBi (26mg), phthalic acid (26mg), phthalic acid (26mg) and Zn (NO3)2,
(CH3COO)2Zn, Zn (SO4) one of zinc salt (52mg) according to the mass ratio of 1:1:1:2 in C2H5OH, CH3OH, H2O,
It is sufficiently mixed stirring in the combination solution of the one or more substance such as DMF, DMA, DMSO, is subsequently placed in polytetrafluoroethyllining lining
In, it is reacted in 24~48h at 60~90 DEG C, obtains colorless and transparent monocrystalline.
Embodiment 3:
Synthetic ligands bbi first: weighing a certain amount of imidazoles 7.8g, and NaOH 5.1g and urea 7.6g are dissolved in H2O, DMA,
DMSO, DMF, C2H5OH, CH3It in the combination solution 10mL of the one or several kinds such as OH, is thoroughly mixed, 50 in oil bath pan
1.5~12h is reacted at~70 DEG C, then weighs the 1,1-C of 0.165mol4H8Cl2, 1,2-C4H8Cl2, 1,3-C4H8Cl2, Isosorbide-5-Nitrae-
C4H8Cl2, 2,2-C4H8Cl2And 2,3-C4H8Cl2One or several kinds of combinations be added in above-mentioned solution several times, continue 5~
After 8h, solution immersion is contained into 500mLH2O,DMA,DMSO,DMF,C2H5OH,CH3The ice water of the one or more combinations such as OH is mixed
It closes in solution, stands a night, obtain a large amount of product as white needles, suction filtration obtains white needle-like crystals, is put into vacuum oven
Drying for standby.
It weighs a certain amount of BBi (45mg), phthalic acid (45mg), phthalic acid (45mg) and Zn (NO3)2,
(CH3COO)2Zn, Zn (SO4) one of zinc salt (90mg) according to the mass ratio of 1:1:1:2 in C2H5OH, CH3OH, H2O,
It is sufficiently mixed stirring in the combination solution of the one or more substance such as DMF, DMA, DMSO, is subsequently placed in polytetrafluoroethyllining lining
In, it is reacted in 24~48h at 60~90 DEG C, obtains colorless and transparent monocrystalline.
Detection of the embodiment 4:MOF-Zn as fluorescence probe to AA
The AA solution of 100~150 μ L is added into MOF-Zn solution, is separately added into L-Phe, Urea, β-Ala, L-Asp,
DL-Pro, L-Val, L-Glu, Arg, Gly, L-Pyr, Suc, LAC, CTS, D-Glc, MEL, CA, L-Lys, L-His, L-Leu,
L-Met, L-Ser, L-Thr, AA.AA significantly decreases to the fluorescence of MOF-Zn solution in Fig. 4.
In MOF-Zn solution, when the amount of AA increases to 90 μ L from 0 μ L, the fluorescence intensity of MOF-Zn it is dull and sharply under
It drops, with the increase of AA concentration in Fig. 9, the fluorescence intensity of MOF-Zn solution is gradually quenched.This shows that MOF-Zn is visited as fluorescence
Needle can be highly sensitive to AA.It can also be counted with quantitative interpretation fluorescent quenching efficiency by Stern-Volmer (SV) equation
Calculate detection limit: wherein I0Fluorescence intensity before being analyte, I are the fluorescence intensities after analyte, and Ksv is quenching constant (M-1), [Q] is the molar concentration of analyte.When AA concentration increases to 0.071mM, almost quench.According to the number in Fig. 5
According to.The standard deviation (σ) of duplicate measurements three times based on blank solution fluorescence intensity, detection limit (3 σ/Ksv) are calculated as
1.704ppb。
150uL amino acid and other substances (L-Phe, Urea, β-Ala, L-Asp, DL- are added into MOF-Zn solution
Pro, L-Val, L-Glu, Arg, Gly, L-Pyr, Suc, LAC, CTS, D-Glc, MEL, CA, L-Lys, L-His, L-Leu, L-
Met, L-Ser, L-Thr etc.), then 40 μ L AA are added thereto, so that in the case that it is there are AA while there is also other
Ion.The fluorescence intensity that compounding substances (M+AA) all mixed solutions are added in Fig. 7 is all quenched, and illustrates that other substances are not done
Disturb the detection to AA.
It should be understood that for those of ordinary skills, it can be modified or changed according to the above description,
And all these modifications and variations should all belong to the protection domain of appended claims of the present invention.
Claims (9)
1. a kind of preparation method of metal organic framework MOF-Zn fluorescent sensor material, which is characterized in that the preparation method is as follows:
The preparation of BBi ligand: a certain amount of imidazoles, NaOH, KOH, Ca (OH) are weighed2One of or several alkali and CH4N2O is molten
In H2O, DMA, DMSO, DMF, C2H5OH, CH3In the combination solution of OH one or several kinds, it is thoroughly mixed, in oil bath pan
In 1.5~12h is reacted at 50~70 DEG C, then weigh a certain amount of 1,1-C4H8Cl2, 1,2-C4H8Cl2, 1,3-C4H8Cl2, 1,
4-C4H8Cl2, 2,2-C4H8Cl2And 2,3-C4H8Cl2One or several kinds of combinations, be added in above-mentioned solution, continue several times
After 5~8h, solution immersion is contained into H2O,DMA,DMSO,DMF,C2H5OH,CH3The ice water mixing of OH one or more combination is molten
In liquid, a night is stood, obtains a large amount of product as white needles, suction filtration obtains white needle-like crystals, is put into vacuum oven dry
It is spare；
Hydro-thermal method prepares MOF-Zn: weighing BBi, phthalic acid, phthalic acid and Zn (NO3)2, (CH3COO)2Zn, ZnSO4
One of zinc salt in C2H5OH, CH3OH, H2It is sufficiently mixed in the combination solvent of O, DMF, DMA, DMSO one or more substance
Stirring is closed, is subsequently placed in polytetrafluoroethyllining lining, is reacted in 24~48h at 60~90 DEG C, obtains colorless and transparent monocrystalline.
2. preparation method according to claim 1, which is characterized in that imidazoles, NaOH, KOH, Ca (OH)2It is one of or several
Kind alkali, CH4N2O three's molar ratio is 1:1:1.
3. preparation method according to claim 1, which is characterized in that 1,1-C4H8Cl2, 1,2-C4H8Cl2, 1,3-
C4H8Cl2, Isosorbide-5-Nitrae-C4H8Cl2, 2,2-C4H8Cl2And 2,3-C4H8Cl2One or several kinds of combined moles be imidazoles,
NaOH、KOH、Ca(OH)2One of or several alkali, CH4N22 times of the sum of O three's mole.
4. preparation method according to claim 1, which is characterized in that BBi, phthalic acid, phthalic acid, Zn
(NO3)2, (CH3COO)2Zn, ZnSO4One of zinc salt, four mass ratioes be 1:1:1:2.
5. preparation method according to claim 1, which is characterized in that synthetic ligands bbi first: weigh a certain amount of imidazoles
(2.0g and urea 3.0g are dissolved in H by 3.4g, NaOH2O, DMA, DMSO, DMF, C2H5OH, CH3The combination of OH one or several kinds is molten
It in liquid 10mL, is thoroughly mixed, reacts 1.5~12h at 50~70 DEG C in oil bath pan, then weigh the 1,1- of 0.075mol
C4H8Cl2, 1,2-C4H8Cl2, 1,3-C4H8Cl2, Isosorbide-5-Nitrae-C4H8Cl2, 2,2-C4H8Cl2And 2,3-C4H8Cl2One or several kinds
Combination be added in above-mentioned solution several times, after continuing 5~8h, by solution immersion contain 500mLH2O, DMA, DMSO, DMF,
C2H5OH, CH3In the ice water mixed solution of OH one or more combination, a night is stood, a large amount of product as white needles are obtained, filtered
White needle-like crystals are obtained, drying for standby in vacuum oven is put into；
Weigh BBi15mg, phthalic acid 15mg, phthalic acid 15mg and Zn (NO3)2, (CH3COO)2Zn, ZnSO4Wherein
A kind of zinc salt 30mg is in C2H5OH, CH3OH, H2It is sufficiently mixed in the combination solution of O, DMF, DMA, DMSO one or more substance
Stirring, is subsequently placed in polytetrafluoroethyllining lining, reacts in 24~48h at 60~90 DEG C, obtains colorless and transparent monocrystalline.
6. preparation method according to claim 1, which is characterized in that synthetic ligands bbi first: weighing imidazoles 6.8g,
NaOH 4.0g and urea 6.0g are dissolved in H2O, DMA, DMSO, DMF, C2H5OH, CH3The combination solution 10mL of OH one or several kinds
In, it is thoroughly mixed, reacts 1.5~12h at 50~70 DEG C in oil bath pan, then weigh the 1,1-C of 0.15mol4H8Cl2,
1,2-C4H8Cl2, 1,3-C4H8Cl2, Isosorbide-5-Nitrae-C4H8Cl2, 2,2-C4H8Cl2And 2,3-C4H8Cl2One or several kinds of combinations point
It is repeatedly added in above-mentioned solution, after continuing 5~8h, solution immersion is contained into 500mLH2O,DMA,DMSO,DMF,C2H5OH,
CH3In the ice water mixed solution of OH one or more combination, a night is stood, obtains a large amount of product as white needles, suction filtration obtains white
Color acicular crystal is put into drying for standby in vacuum oven；
Weigh BBi26mg, phthalic acid 26mg, phthalic acid 26mg and Zn (NO3)2, (CH3COO)2Zn, Zn (SO4) its
A kind of middle zinc salt 52mg is in C2H5OH, CH3OH, H2It is sufficiently mixed in the combination solution of O, DMF, DMA, DMSO one or more substance
Stirring is closed, is subsequently placed in polytetrafluoroethyllining lining, is reacted in 24~48h at 60~90 DEG C, obtains colorless and transparent monocrystalline.
7. preparation method according to claim 1, which is characterized in that synthetic ligands bbi first: weighing imidazoles 7.8g,
NaOH 5.1g and urea 7.6g are dissolved in H2O, DMA, DMSO, DMF, C2H5OH, CH3The combination solution 10mL of OH one or several kinds
In, it is thoroughly mixed, reacts 1.5~12h at 50~70 DEG C in oil bath pan, then weigh the 1,1- of 0.165mol
C4H8Cl2, 1,2-C4H8Cl2, 1,3-C4H8Cl2, Isosorbide-5-Nitrae-C4H8Cl2, 2,2-C4H8Cl2And 2,3-C4H8Cl2One or several kinds
Combination be added in above-mentioned solution several times, after continuing 5~8h, by solution immersion contain 500mLH2O,DMA,DMSO,DMF,
C2H5OH,CH3In the ice water mixed solution of OH one or more combination, a night is stood, a large amount of product as white needles are obtained, filtered
White needle-like crystals are obtained, drying for standby in vacuum oven is put into；
Weigh BBi 45mg, phthalic acid 45mg, phthalic acid 45mg and Zn (NO3)2, (CH3COO)2Zn, Zn (SO4)
One of zinc salt 90mg is in C2H5OH, CH3OH, H2In the combination solution of O, DMF, DMA, DMSO one or more substance sufficiently
It is mixed, is subsequently placed in polytetrafluoroethyllining lining, reacted in 24~48h at 60~90 DEG C, obtain colorless and transparent monocrystalline.
8. the metal organic framework MOF-Zn fluorescent sensor material of -7 any the method preparations according to claim 1.
9. metal organic framework MOF-Zn fluorescent sensor material answering in detection ascorbic acid according to claim 8
With being detected using MOF-ZnMOF-Zn fluorescent sensor material as fluorescence probe Ascorbic Acid.
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