CN110015989A - Application of the equal benzene trimellitic imide of 4-aminopyridine functionalization in detection nitrate ion - Google Patents
Application of the equal benzene trimellitic imide of 4-aminopyridine functionalization in detection nitrate ion Download PDFInfo
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- CN110015989A CN110015989A CN201910302745.6A CN201910302745A CN110015989A CN 110015989 A CN110015989 A CN 110015989A CN 201910302745 A CN201910302745 A CN 201910302745A CN 110015989 A CN110015989 A CN 110015989A
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- equal benzene
- functionalization
- aminopyridine
- benzene trimellitic
- trimellitic imide
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- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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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"
- 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
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- 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
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- 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
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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"
- G01N2021/6443—Fluorimetric titration
Abstract
The invention discloses the equal benzene trimellitic imides of 4-aminopyridine functionalization in detection NO3 ‑Application, be the equal benzene trimellitic imide ultrasonic disperse by 4-aminopyridine functionalization in pure water, then Th is added thereto4+, 50 ~ 60 DEG C are heated to, suspension dissolves to obtain the colourless solution of clear, then is separately added into F in the colourless solution of clear‑, Cl‑, Br‑, I‑, NO3 ‑, AcO‑, H2PO4 ‑, SO4 ‑, ClO4 ‑, CN‑, SCN‑, N3 ‑And OH‑Solution, only as addition NO3 ‑When, the colourless solution of clear is muddy and its fluorescence enhancement, lowest detection are limited to 3.29 × 10‑10M.Therefore, the equal benzene trimellitic imide of 4-aminopyridine functionalization is coordinated Th4+After can be used for selective hypersensitive identification NO3 ‑。
Description
Technical field
The present invention relates to a kind of new applications of the equal benzene trimellitic imide of 4-aminopyridine functionalization --- and its complex is used
In detection NO3 -, belong to the field of ion detection.
Background technique
The equal benzene trimellitic imide of aminopyridine functionalization is existed by 1,3,5- equal benzene trimellitic imide and 4-aminopyridine
It reacts and obtains in DMF.Its structural formula is as follows:
Currently, the equal benzene trimellitic imide class compound of aminopyridine functionalization has mainly as gelator applied to supermolecule
The preparation of machine gel.But it is used for fluorescence detection NO as sensor3 -Document have not been reported yet.
Summary of the invention
The object of the present invention is to provide a kind of equal benzene trimellitic imides of 4-aminopyridine functionalization to detect NO3 -Method.
1, to the detection of nitrate anion
The preparation of water-soluble supermolecule polymer solution: by the equal benzene trimellitic imide (being labeled as Q) of 4-aminopyridine functionalization
For ultrasonic disperse in pure water, obtaining concentration is 5.0 ~ 6.0 mg/mL(1.0 × 10-2~1.2×10-2M water slurry)；Again to
Th is wherein added4+(the equal benzene trimellitic imide and Th of 4-aminopyridine functionalization4+Molar ratio be 1:3 ~ 1:3.1), be heated to
50 ~ 60 DEG C of suspension dissolutions, obtain the colourless solution of clear, and as water-soluble supermolecule polymer solution is labeled as QT.
The equal benzene trimellitic imide etc. of 4-aminopyridine functionalization is separately added into water-soluble supermolecule polymer solution
The F of mole-, Cl-, Br-, I-, NO3 -, AcO-, H2PO4 -, SO4 -, ClO4 -, CN-, SCN-, N3 -And OH-Solution (0.1M), can be with
It was found that only as addition NO3 -Water solubility supermolecule polymer solution (QT) is by clear to muddy and its fluorescence when solution
When enhancing, and other anion of equivalent are added, water-soluble supermolecule polymer fluorescence does not enhance (see figure 1).Cause
This, the equal benzene trimellitic imide of 4-aminopyridine functionalization can be used for Selective recognition NO3 -。
2, interference--free experiments
Anion interference--free experiments: containing different anions (F respectively-, Cl-, Br-, I-, NO3 -, AcO-, H2PO4 -, SO4 -,
ClO4 -, CN-, SCN-, N3 -And OH-Solution) QT in be sequentially added into NO3 -When, the above-mentioned QT containing different anions is muddy
It is turbid, and its fluorescence enhancement (shown in Fig. 2).By QT aqueous solution to NO3 -The interference--free experiments of detection, it was demonstrated that other may be total to
The anion deposited detects NO to QT3 -There is no interference.Therefore, QT can highly selective detection NO3 -。
Cationic interference--free experiments: a series of nitrate (NaNO are separately added into QT3, KNO3, LiNO3, Ba
(NO3)2, Ca(NO3)2, Co(NO3)2, Mg(NO3)2, Al(NO3)3, Fe(NO3)3, Hg(NO3)2, Pb(NO3)2,
AgNO3, Cu(NO3)2) when, the above-mentioned QT containing different cations is muddy, and its fluorescence enhancement (Fig. 3).It is water-soluble by QT
Liquid is to NO3 -The cationic interference--free experiments of detection, it was demonstrated that other can compatible cation NO is detected to QT3 -There is no dry
It disturbs.Therefore, QT can highly selective detection NO3 -。
3, to the sensitivity of the detection of nitrate anion
Fig. 4 is water solubility supermolecule polymer solution QT to nitrate anion fluorescence titration figure.It can be obtained by fluorescence titration experiment, with
Nitrate ion concentration in water-soluble supermolecule polymer (QT) solution is continuously increased, it is found that its fluorescence intensity constantly increases
By force, when nitrate anion equivalent is 0.85, fluorescence intensity reaches balance, obtains water-soluble supermolecule polymer solution by 3 σ methods
QT is limited to 3.29 × 10 to the detection of nitrate anion-10M, thus reached the level of super sensitivity detection.
4, to the mechanism of the detection of nitrate anion
The IR that Fig. 5 is QT schemes.It can be obtained by infrared experiment, the NH stretching vibration peak of compound Q T is respectively in 3414 cm-1, work as nitre
After acid ion is added, movement is had occurred in NH stretching vibration peak, is moved to 3434cm-1, illustrate nitrate ion and the NH of QT
It is interacted by hydrogen bond.
Fig. 6 is QT and QT+NO3 -SEM figure.Illustrated by scanning electron microscope, by NO3 -It is added to water-soluble supermolecule
After polymer QT, the configuration of surface of QT changes into porous network structure by crosslinking net.This also further illustrate nitrate anion from
The NH of son and QT are interacted by hydrogen bond.
Detailed description of the invention
Fig. 1 is water solubility supermolecule polymer solution QT to different anion full scan fluorograms.
Fig. 2 be water solubility supermolecule polymer solution QT detection nitrate anion anion interference--free experiments picture (1- blank,
2-F-, 3- Cl-, 4-Br-, 5-I-, 6- NO3 -, 7-AcO-, 8-H2PO4 -, 9-HSO4 -, 10-ClO4 -, 11- CN-, 12- SCN-,
13-N3 -, 14-OH-).
Fig. 3 is the cationic interference--free experiments picture that water solubility supermolecule polymer solution QT detects nitrate anion.
Fig. 4 is water solubility supermolecule polymer solution QT to nitrate anion fluorescence titration figure.
Fig. 5 is the IR figure of water-soluble supermolecule polymer solution QT.
Fig. 6 is QT and QT+NO3 -SEM figure.
Fig. 7 is the hydrogen spectrogram of the equal benzene trimellitic imide of aminopyridine functionalization.
Specific embodiment
Below by the equal benzene trimellitic imide unicity selection identification nitric acid of specific embodiment P-aminopyridine functionalization
The method of root is described further.
1, the synthesis of the equal benzene trimellitic imide Q of 4-aminopyridine functionalization
3.2 mmol 4-aminopyridines (0.300g) are taken, are dissolved in 15mL DMF solution, then take 1mmol pyromellitic trimethylsilyl chloride
(0.264g) is added drop-wise in DMF solution, and it is overnight to react 12 ~ 14h(at room temperature), then recrystallized with DMF and water, obtain 0.422g
The equal benzene trimellitic imide (DTA) of 4-aminopyridine functionalization, yield 97%.Fig. 7 is the hydrogen spectrogram of Q.
2, the equal benzene trimellitic imide QT of 4-aminopyridine functionalization detects NO3 -
The equal benzene trimellitic imide Q for taking 5 mg 4-aminopyridine functionalization, is scattered in 1 ml pure water, and 5 mg/mL of concentration is made
Suspension in；3 μ L Th (NO are added3)4Solution (0.1 M) is heated to 50-60 DEG C, and suspension dissolution becomes clear
Colourless solution is cooled to room temperature, i.e., water-soluble supermolecule polymer solution (QT) (1 × 10-2M)；
Take 2mL water solubility supermolecule polymer (QT) (1 × 10-2M in), it is separately added into F-, Cl-, Br-, I-, NO3 -, AcO-,
H2PO4 -, SO4 -, ClO4 -, CN-, SCN-, N3 -And OH-Solution, if water-soluble supermolecule polymer solution becomes muddy from clear
It is turbid, and its fluorescence enhancement, that illustrate to be added is NO3 -Solution；If there is no muddinesses for water-soluble supermolecule polymer solution, and
For its fluorescence there is no significantly changing, illustrate to be added is other ions.
Claims (4)
- Application of the equal benzene trimellitic imide of 1.4- aminopyridine functionalization in detection nitrate ion, it is characterised in that: by ammonia The equal benzene trimellitic imide ultrasonic disperse of yl pyridines functionalization obtains water slurry in pure water；It is added again into water slurry Th4+, 50 ~ 60 DEG C are heated to, suspension dissolves to obtain the colourless solution of clear；Then in the colourless solution of clear It is separately added into F-, Cl-, Br-, I-, NO3 -, AcO-, H2PO4 -, SO4 -, ClO4 -, CN-, SCN-, N3 -And OH-Solution only works as addition NO3 -When solution, the colourless solution muddiness and fluorescence enhancement of clear；Three formyl of equal benzene of the aminopyridine functionalization is sub- The structural formula of amine is as follows:。
- 2. the equal benzene trimellitic imide of 4-aminopyridine functionalization as described in claim 1 detection nitrate ion application, It is characterized by: the concentration of the water slurry is 5.0 ~ 6.0 mg/mL.
- 3. the equal benzene trimellitic imide of 4-aminopyridine functionalization as described in claim 1 detection nitrate ion application, It is characterized by: Th4+From Th (NO3)4。
- 4. the application of the equal benzene trimellitic imide detection nitrate ion of 4-aminopyridine functionalization as described in claim 1, It is characterized in that: the equal benzene trimellitic imide and Th of 4-aminopyridine functionalization4+Molar ratio be 1:3 ~ 1:3.1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115181279A (en) * | 2022-06-08 | 2022-10-14 | 渤海大学 | Fluorescent metal-organic framework material for detecting human biomarker 3-nitrotyrosine and application thereof |
Citations (2)
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| CN109265398A (en) * | 2018-09-12 | 2019-01-25 | 西北师范大学 | A kind of application of supramolecular organogel and its fluorescence identifying mercury ion |
| CN109320454A (en) * | 2018-11-29 | 2019-02-12 | 西北师范大学 | The preparation and application of a kind of bi-component supramolecular organogel and its metal gel |
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Patent Citations (2)
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|---|---|---|---|---|
| CN109265398A (en) * | 2018-09-12 | 2019-01-25 | 西北师范大学 | A kind of application of supramolecular organogel and its fluorescence identifying mercury ion |
| CN109320454A (en) * | 2018-11-29 | 2019-02-12 | 西北师范大学 | The preparation and application of a kind of bi-component supramolecular organogel and its metal gel |
Non-Patent Citations (2)
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| YAN-QING FAN，等: "An easy-to-make strong white AIE supramolecular polymer as a colour tunable photoluminescence material", 《J. MATER. CHEM. C》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115181279A (en) * | 2022-06-08 | 2022-10-14 | 渤海大学 | Fluorescent metal-organic framework material for detecting human biomarker 3-nitrotyrosine and application thereof |
| CN115181279B (en) * | 2022-06-08 | 2023-05-12 | 渤海大学 | Fluorescent metal-organic framework material for detecting biomarker 3-nitrotyrosine of human body and application thereof |
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Granted publication date: 20210716 |