CN110015989B - Application of 4-aminopyridine functionalized trimesoimide in detecting nitrate ions - Google Patents

Application of 4-aminopyridine functionalized trimesoimide in detecting nitrate ions Download PDF

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CN110015989B
CN110015989B CN201910302745.6A CN201910302745A CN110015989B CN 110015989 B CN110015989 B CN 110015989B CN 201910302745 A CN201910302745 A CN 201910302745A CN 110015989 B CN110015989 B CN 110015989B
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trimesoimide
aminopyridine
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water
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林奇
樊彦青
安军年
姚虹
张有明
魏太保
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Northwest Normal University
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Abstract

The invention discloses the detection of NO by 4-aminopyridine functionalized trimesoimide3 ‑The application of (1) is that 4-aminopyridine functionalized trimesoimide is dispersed in pure water by ultrasonic, and Th is added into the pure water4+Heating to 50-60 ℃, dissolving the suspension to obtain clear and transparent colorless solutions, and respectively adding F into the clear and transparent colorless solutions‑，Cl‑，Br‑，I‑，NO3 ‑，AcO‑，H2PO4 ‑，SO4 ‑，ClO4 ‑，CN‑，SCN‑，N3 ‑And OH‑Solution, only when NO is added3 ‑When clear and transparent colorless solution is turbid and its fluorescence is enhanced, the lowest detection limit is 3.29X 10‑10And M. Thus, 4-aminopyridine-functionalized trimesoimide-coordinated Th4+Can be used for selectively and ultra-sensitively identifying NO3 ‑。

Description

Application of 4-aminopyridine functionalized trimesoimide in detecting nitrate ions
Technical Field
The invention relates to a new application of 4-aminopyridine functionalized trimesoimide-a complex thereof for detecting NO3 -Belonging to the field of ion detection.
Background
Aminopyridine-functionalized trimesoimide is obtained by reacting 1,3, 5-trimesoimide with 4-aminopyridine in DMF. The structural formula is as follows:
Figure 100002_DEST_PATH_IMAGE001
at present, the number of the current day,the aminopyridine functionalized trimesoimide compound is mainly used as a gelator to be applied to the preparation of supermolecule organogel. But it is used as a sensor for the fluorescence detection of NO3 -The literature of (A) has not been reported at present.
Disclosure of Invention
The invention aims to provide 4-aminopyridine functionalized trimesoimide for detecting NO3 -The method of (1).
1. Detection of nitrate radical
Preparation of water-soluble supramolecular polymer solution: ultrasonically dispersing 4-aminopyridine functionalized trimesoimide (marked as Q) in pure water to obtain the product with the concentration of 5.0-6.0 mg/mL (1.0 multiplied by 10)-2~1.2×10-2M) an aqueous suspension; adding Th thereto4+(4-aminopyridine-functionalized trimesoimide and Th4+The molar ratio of (1: 3) - (1: 3.1), heating to 50-60 ℃, and dissolving the suspension to obtain a clear and transparent colorless solution, namely a water-soluble supramolecular polymer solution, which is marked as QT.
Adding 4-aminopyridine functionalized trimesoimide F with equimolar amount into water-soluble supermolecular polymer solution-，Cl-，Br-，I-，NO3 -，AcO-，H2PO4 -，SO4 -，ClO4 -，CN-，SCN-，N3 -And OH-Solution (0.1M), it was found that only when NO was added3 -The water soluble supramolecular polymer solution (QT) goes from clear to turbid in solution and its fluorescence increases, while the water soluble supramolecular polymer fluorescence does not increase when an equivalent amount of other anions is added (see figure 1). Thus, 4-aminopyridine-functionalized trimesoimides are useful for selective recognition of NO3 -。
2. Anti-interference experiment
Anion anti-interference experiment: in the presence of different anions (F)-，Cl-，Br-，I-，NO3 -，AcO-，H2PO4 -，SO4 -，ClO4 -，CN-，SCN-，N3 -And OH-Solutions) QT separately and sequentially NO3 -When the above QTs containing different anions are all turbid, their fluorescence is enhanced (shown in FIG. 2). By QT in water on NO3 -The anti-interference test of detection proves that other possible coexisting anions can detect NO in QT3 -There is no interference. Therefore, NO which QT can detect with high selectivity3 -。
Cation anti-interference experiment: respectively adding a series of nitrates (NaNO) 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 QT containing different cations as described above is cloudy, its fluorescence increases (FIG. 3). By QT in water on NO3 -The anti-interference experiment of the detected cations proves that other possible coexisting cations can detect NO in QT3 -There is no interference. Therefore, NO which QT can detect with high selectivity3 -。
3. Sensitivity to detection of nitrate
FIG. 4 is a fluorescent titration graph of QT vs. nitrate for a water-soluble supramolecular polymer solution. The fluorescence titration experiment can show that the fluorescence intensity of the water-soluble supramolecular polymer (QT) solution is continuously enhanced along with the continuous increase of the concentration of nitrate ions in the water-soluble supramolecular polymer (QT) solution, when the equivalent of nitrate is 0.85, the fluorescence intensity of the water-soluble supramolecular polymer solution is balanced, and the detection limit of the water-soluble supramolecular polymer solution QT obtained by a 3 sigma method on nitrate is 3.29 multiplied by 10-10M, thereby achieving the level of ultra-sensitive detection.
4. Mechanism of detection of nitrate radical
FIG. 5 is the IR diagram of QT. The NH stretching vibration peak of the compound QT is 3414 cm respectively through infrared experiments-1When nitrate ions are added, the NH stretching vibration peak moves to 3434cm-1Indicating that the nitrate ion and NH of QT interact through hydrogen bonds.
FIG. 6 shows QT and QT + NO3 -SEM image of (d). By scanning Electron microscopy, in the description of NO3 -After the water-soluble supermolecule polymer QT is added, the surface morphology of the QT is changed into a porous network structure from a cross-linked network. This further illustrates that the nitrate ion and NH of QT interact via hydrogen bonds.
Drawings
FIG. 1 shows the fluorescence of a water-soluble supramolecular polymer solution QT for different anions under full scan.
FIG. 2 is a picture of an anion anti-interference experiment for detecting nitrate radical by water-soluble supramolecular polymer solution QT (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 a picture of a cation anti-interference experiment for detecting nitrate by using a water-soluble supramolecular polymer solution QT.
FIG. 4 is a fluorescent titration graph of QT vs. nitrate for a water-soluble supramolecular polymer solution.
Figure 5 is an IR diagram of a water-soluble supramolecular polymer solution QT.
FIG. 6 shows QT and QT + NO3 -SEM image of (d).
FIG. 7 is a hydrogen spectrum of aminopyridine-functionalized trimesoimide.
Detailed Description
The method for identifying nitrate by the single selection of aminopyridine-functionalized trimesoimide is further illustrated by the following specific examples.
1. Synthesis of 4-aminopyridine-functionalized trimesoimide Q
Dissolving 3.2 mmol of 4-aminopyridine (0.300 g) in 15mL of DMF solution, dropwise adding 1mmol of trimesoyl chloride (0.264 g) into the DMF solution, reacting at room temperature for 12-14 h (overnight), and recrystallizing with DMF and water to obtain 0.422g of 4-aminopyridine functionalized trimesoimide (DTA) with the yield of 97%. FIG. 7 is a hydrogen spectrum of Q.
2. 4-aminopyridine functionalized trimesoimide QT detection of NO3 -
5 mg of 4-aminopyridine functionalized trimesoimide Q is taken and dispersed in 1 mL of pure water to prepare suspension with the concentration of 5 mg/mL; adding 3 μ L of Th (NO)3)4Heating the solution (0.1M) to 50-60 deg.C, dissolving the suspension to obtain clear and transparent colorless solution, and cooling to room temperature to obtain water-soluble supramolecular polymer solution (QT) (1 × 10)-2 M）；
2mL of water-soluble supramolecular polymer (QT) (1X 10)-2M) in each case, F is added-，Cl-，Br-，I-，NO3 -，AcO-，H2PO4 -，SO4 -，ClO4 -，CN-，SCN-，N3 -And OH-Solution, if the water-soluble supramolecular polymer solution changes from clear to turbid and its fluorescence increases, indicating that NO is added3 -A solution; if the water-soluble supramolecular polymer solution is not turbid and the fluorescence does not change significantly, it is indicated that other ions are added.

Claims (4)

  1. The application of 4-aminopyridine functionalized trimesoimide in detecting nitrate ions is characterized in that: ultrasonically dispersing aminopyridine functionalized trimesoimide into pure water to obtain a water suspension; adding Th to the aqueous suspension4+Heating to 50-60 ℃, and dissolving the suspension to obtain a clear and transparent colorless solution; then in clear and transparent colorlessAdding F into the solution respectively-，Cl-，Br-，I-，NO3 -，AcO-，H2PO4 -，SO4 -，ClO4 -，CN-，SCN-，N3 -And OH-Solution, only when NO is added3 -Clear, transparent, colorless solutions are turbid and fluorescence increases upon solution; the structural formula of the aminopyridine functionalized trimesoimide is as follows:
    Figure DEST_PATH_IMAGE001
    。
  2. 2. use of 4-aminopyridine-functionalized trimesoimide according to claim 1 for the detection of nitrate ions, wherein: the concentration of the water suspension is 5.0-6.0 mg/mL.
  3. 3. Use of 4-aminopyridine-functionalized trimesoimide according to claim 1 for the detection of nitrate ions, wherein: th4+Derived from Th (NO)3)4。
  4. 4. Use of 4-aminopyridine-functionalized trimesoimide according to claim 1 for the detection of nitrate ions, wherein: 4-aminopyridine functionalized trimesoimide and Th4+The molar ratio of (a) to (b) is 1:3 to 1: 3.1.
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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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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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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* Cited by examiner, † Cited by third party
Title
An easy-to-make strong white AIE supramolecular polymer as a colour tunable photoluminescence material;Yan-Qing Fan，等;《J. Mater. Chem. C》;20181120;13331-13335 *
刺激响应型超分子凝胶;逯桃桃，等;《化学进展》;20181231;1541-1549 *

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