CN109971465B - Multifunctional fluorescent probe with ESIPT (electron fluorescence tomography) and AIE (electron emission tomography) properties and preparation method and application thereof - Google Patents
Multifunctional fluorescent probe with ESIPT (electron fluorescence tomography) and AIE (electron emission tomography) properties and preparation method and application thereof Download PDFInfo
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Abstract
A multifunctional fluorescent probe with ESIPT and AIE properties, a preparation method and an application thereof, wherein the preparation method of the fluorescent probe comprises the following steps: dissolving 2-picolinic acid in dry dichloromethane, adding benzotriazole-N, N, N ', N ' -tetramethylurea hexafluorophosphate, stirring for 30 minutes, then adding 2- (2 ' -aminophenyl) benzothiazole and triethylamine, and stirring at room temperature overnight; and after the reaction is finished, evaporating the solvent under reduced pressure, and separating the residue by column chromatography to obtain the fluorescent probe N- (2- (2' -benzothiazolyl) phenyl) picolinamide. The fluorescent probe has the advantages of simple synthesis method, easy product separation and purification process, ESIPT + AIE property, capability of being used for monitoring, analyzing and tracing copper ions and pyrophosphate in a water environment system, and good sensitivity for measuring target ions.
Description
Technical Field
The invention relates to the field of functional materials, in particular to a multifunctional fluorescent probe with ESIPT and AIE properties, and a preparation method and application thereof.
Background
Fluorescence recognition of copper ions and pyrophosphate (PPi) is of great significance in life sciences, environmental monitoring and the like, and has been receiving attention in recent years. The relay identification enables the identification operation of two ions to be continuously carried out under the same test condition, and has the obvious advantage of simple operation. Many of the currently reported fluorescent probes capable of identifying copper ions and pyrophosphate in a relay manner need to be used in a mixed solvent containing more organic solvents, and are not beneficial to environmental protection. Few fluorescent probes capable of recognizing copper ions and pyrophosphate in aqueous solution have the defect of complex synthesis process.
By utilizing the property of Excited State Intramolecular Proton Transfer (ESIPT), long fluorescence emission can be obtained by a small-molecule fluorophore, but when the probe is used in a mixed solvent with high water content, the probe is limited by aggregation-induced quenching (ACQ) effect due to poor solubility.
At present, ESIPT and AIE properties are possessed, and a fluorescence probe capable of relay recognition of copper ions and pyrophosphate in a solvent with high water content is not reported in documents. Therefore, one probe molecule is endowed with multiple recognition functions, and the recognition operation can be completed under the same condition, so that the recognition process of multiple ions can be greatly simplified.
Disclosure of Invention
The invention aims to solve the technical problem of providing a multifunctional fluorescent probe with ESIPT and AIE properties, a preparation method and application thereof, the synthetic method is simple, the product separation and purification process is easy, the obtained fluorescent probe can relay and identify copper ions and pyrophosphate in a solvent with high water content, and the sensitivity is good.
The invention adopts the specific technical scheme that the purpose is realized by the following steps:
a multifunctional fluorescent probe with ESIPT and AIE properties has the following structural formula:
a preparation method of a multifunctional fluorescent probe with ESIPT and AIE properties comprises the following specific steps:
weighing 0.185g of 2-picolinic acid, dissolving the 2-picolinic acid in 15mL of dry dichloromethane, adding 0.682g of benzotriazole-N, N, N ', N ' -tetramethyluronium Hexafluorophosphate (HBTU), stirring for 30 minutes, then adding 0.226g of 2- (2 ' -aminophenyl) benzothiazole and 0.181g of triethylamine, and stirring at room temperature overnight; and (3) after the reaction is finished, evaporating the solvent under reduced pressure, and separating the residue by column chromatography to obtain the compound.
Preferably, the room-temperature reaction temperature is 25 ℃, and the room-temperature reaction time is 12 h.
Preferably, the eluent is ethyl acetate and petroleum ether in a volume ratio of 1: 10.
The application of the relay type multifunctional fluorescent probe is to the detection and tracing of copper ions and pyrophosphate in a water environment system.
Preferably, the relay type multifunctional fluorescent probe is prepared by mixing DMF and H at the pH value of 7.1 and the volume ratio of 1:92And detecting copper ions under a Tris buffer solution system of 10mmol/L of O.
Preferably, 10 mu mol/L Tris buffer solution of the relay type multifunctional fluorescent probe is added into a detection water sample, and fluorescence quenching can occur, which indicates that the detection water sample contains copper ions.
Preferably, the relay type multifunctional fluorescent probe is prepared by mixing DMF and H at the pH value of 7.1 and the volume ratio of 1:92Detecting copper ions in a Tris buffer solution system of 10mmol/L of O, quenching fluorescence, and continuously recognizing pyrophosphate (PPi) in the system.
Preferably, Tris buffer solution of the relay type multifunctional fluorescent probe after detecting and fluorescence quenching copper ions is added into a detected water sample, and pyrophosphate is contained if fluorescence emission is enhanced.
The invention has the beneficial effects that:
the relay type multifunctional fluorescent probe provided by the invention has the advantages that the synthetic method is simple, the separation and purification process of the product is easy, the probe has Excited State Intramolecular Proton Transfer (ESIPT) and Aggregation Induced Emission (AIE) properties, the defect of aggregation induced quenching (ACQ) of the traditional fluorescent dye is overcome, the fluorescence can be emitted by limiting intramolecular movement (intramolecular rotation and intramolecular vibration) in an aggregation state, copper ions and pyrophosphate can be recognized in a high-water-content solution in a relay manner, and the sensitivity to the determination of target ions is good; one probe molecule has multiple recognition functions, and the recognition operation can be completed under the same condition, so that the continuous operability is realized, and the recognition process of multiple ions can be greatly simplified.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the relay-type multifunctional fluorescent probe provided by the embodiment of the present invention: (1H NMR) pattern;
FIG. 2 is a nuclear magnetic resonance carbon spectrum of the relay-type multifunctional fluorescent probe provided in the embodiment of the present invention: (13C NMR) pattern;
FIG. 3 is a High Resolution Mass Spectrometry (HRMS) diagram of the relay-type multifunctional fluorescent probe provided by the embodiment of the present invention;
FIG. 4 shows the relay type multifunctional fluorescent probe provided by the embodiment of the invention in DMF/H with different water contents2A graph of the change in fluorescence spectra in O solution;
FIG. 5 shows the fluorescence intensity (557nm) of the relay type multifunctional fluorescent probe provided by the embodiment of the inventionDMF/H of the same water content2Graph of change in O solution;
FIG. 6 is a diagram of the change of the fluorescence emission spectra of the relay-type multifunctional fluorescence probe and its interaction with various metal ions according to the embodiment of the present invention;
FIG. 7 is a diagram showing the change of fluorescence emission spectra of the relay-type multifunctional fluorescent probe in the presence of copper ions of different concentrations ranging from 0. mu. mol/L to 20. mu. mol/L;
FIG. 8 is a graph showing the change of fluorescence emission spectra of the relay-type multifunctional fluorescent probe according to the embodiment of the present invention when other metal ions are added in an amount equimolar to the copper ions;
FIG. 9 is a graph showing the changes of fluorescence emission spectra of the relay-type multifunctional fluorescent probe and the fluorescent probe + copper ion under different pH conditions according to the embodiment of the present invention;
FIG. 10 is a diagram illustrating calculation of detection limits of copper ions by the relay-type multifunctional fluorescence probe according to the embodiment of the present invention;
FIG. 11 is a graph showing the change of fluorescence emission spectra before and after the relay-type multifunctional fluorescent probe-copper ion complex provided by the embodiment of the present invention reacts with various anions;
FIG. 12 is a graph showing the change of fluorescence emission spectra of the relay-type multifunctional fluorescent probe-copper ion complex with 0-350 μmol/L pyrophosphate;
FIG. 13 is a graph showing the change of fluorescence emission spectra of the relay-type multifunctional fluorescent probe-copper ion complex according to the embodiment of the present invention after the addition of pyrophosphate and equimolar amounts of other anions;
FIG. 14 is a graph showing calculation of detection limits of the relay-type multifunctional fluorescent probe-copper ion complex for pyrophosphate according to the embodiment of the present invention.
Detailed Description
The invention will be further elucidated with reference to the drawings and specific embodiments in order to provide a better understanding of the invention.
Examples
(1) Synthesizing a relay type multifunctional fluorescent probe according to a reaction formula:
(2) the method comprises the following specific steps of synthesizing a relay type multifunctional fluorescent probe:
0.185g of 2-picolinic acid was weighed out and dissolved in 15mL of dry dichloromethane, and after adding 0.682g of benzotriazole-N, N, N ', N ' -tetramethyluronium Hexafluorophosphate (HBTU), stirring was carried out for 30 minutes, 0.226g of 2- (2 ' -aminophenyl) benzothiazole and 0.181g of triethylamine were further added, and stirring was carried out at 25 ℃ for 12 hours. After the reaction is finished, the solvent is distilled off under reduced pressure, and the solvent is removed by a solvent with the volume ratio of 1:10, separating the residue by column chromatography through ethyl acetate and petroleum ether eluent to obtain the relay type multifunctional fluorescent probe N- (2- (2' -benzothiazolyl) phenyl) picolinamide with the yield of 90 percent. Melting point: 165.5-166.1 ℃.
The results of the nuclear magnetic analyses are shown in FIGS. 1 to 3:1H NMR(400MHz,DMSO-d6)δ14.15(s,1H),8.98(dd, J＝4.0,8.0Hz,2H),8.33–8.13(m,3H),8.10(t,J＝8.0Hz,1H),8.02(d,J＝8.0Hz,1H),7.76 –7.69(m,1H),7.64(dd,J＝8.0,8.0Hz,2H),7.53(t,J＝8.0Hz,1H),7.32(t,J＝8.0Hz,1H)；13C NMR(100MHz,DMSO-d6)δ167.79,163.75,153.07,150.24,149.34,138.66,137.39, 133.68,132.48,130.73,127.63,127.54,126.55,124.48,123.14,122.94,122.66,120.91,120.28.
HRMS(ESI+)：Calcd for C19H13N3OS[M+Na]+,354.0817；Found:354.0672.
first, DMF-H of fluorescent probe in different water content2Fluorescence spectroscopy in O-mixed solvents
According to DMF-H2O was prepared into 2mL solutions at different volume ratios, 10. mu. mol/L N- (2- (2' -benzothiazolyl) phenyl) picolinamide prepared in example was added to prepare solutions having 99%, 95%, 90%, 80%, 70%, 60%, 50%, 40%, 30%, 20%, 10%, 0% of water content, respectively, and the fluorescence spectra of the respective samples were measured. As shown in FIG. 4, it can be seen that the fluorescence intensity is strongest at a water content of 90%.
II, for copper ion (Cu)2+) And other metalsSelective detection of ions
To 2mL of 10. mu. mol/L of N- (2- (2' -benzothiazolyl) phenyl) picolinamide (relay type multifunctional fluorescent probe) prepared in example, DMF/H was added2To the O (1/9, v/v, Tris 10mmol/L, pH 7.1) system was added 20. mu. mol/L of another metal ion (Ni)2+，Hg2+，Ba2+，Mg2+，K+，Al3+，Mn2+，Pb2+，Na+，Ca2+，Co2+，Cr3+，Ag+， Fe2+，Fe3+，Zn 2+，Cd2+，Cu2+) And detecting the change of the fluorescence spectrum of the solution after 30 min. As shown in FIG. 6, Cu2+Can cause significant fluorescence quenching, other metal ions (Ni)2+，Hg2+，Ba2+，Mg2+，K+，Al3+，Mn2+，Pb2+， Na+，Ca2+，Co2+，Cr3+，Ag+，Fe2+，Fe3 +，Zn2+，Cd2+) Has little influence on the fluorescence spectrum of the relay type multifunctional fluorescent probe.
10μmol/L Cu2+(fluorescent Probe) DMF/H2Adding 0-20 mu mol/L Cu into O (1/9, v/v, Tris 10mmol/L, pH 7.1) system2+The measured changes in the fluorescence spectra are shown in FIG. 7. As can be seen from FIG. 7, with Cu2+The fluorescence intensity of the emission peak at 557nm is continuously weakened, and 20 mu mol/L of Cu is added2+Saturation is reached and fluorescence is completely quenched.
10 μmol/L N- (2- (2' -benzothiazolyl) phenyl) picolinamide (fluorescent probe) DMF/H2Adding 20 mu mol/L of other metal ions and Cu into an O (1/9, v/v, Tris 10mmol/L, pH 7.1) system2+Thereafter, the change in the fluorescence spectrum was measured as shown in the white striped portion of FIG. 8, with only Cu2+Can cause a change in fluorescence. However, on this basis (addition of the further metal ions) a further 20. mu. mol/L Cu addition was continued2+This in turn causes fluorescence quenching, as shown by the black bar in FIG. 8This shows that the coexistence of other metal ions in the solution can not change the probe molecule pair Cu2+Selectivity of (2).
To 10. mu. mol/L N- (2- (2' -benzothiazolyl) phenyl) picolinamide (fluorescent probe) in DMF/H2To a system of O (1/9, v/v, Tris 10mmol/L, pH 7.1) was added Cu of 20. mu. mol/L2+And then carrying out an experiment on the influence of the fluorescence intensity of the fluorescent probe under different acid-base conditions. The results are shown in FIG. 9. The pH value is within 3-12, the fluorescence intensity of the fluorescent probe at 557nm is slightly changed, and when 20 mu mol/L Cu is added2+Then, fluorescence quenching is obvious between pH 5 and 7.4.
Fluorescence probe for Cu based on SNR method2+The limit of detection (LOD: 3. sigma./k, where. sigma. is the standard deviation of the blank solution; k is the slope of the calibration curve) of (A) was calculated to be 5.0X 10-7mol/L。
Thirdly, selective detection of relay recognition pyrophosphate (PPi)
To 2mL of 10. mu. mol/L N- (2- (2' -benzothiazolyl) phenyl) picolinamide and 20. mu. mol/L Cu2+Complex formed after action (fluorescent probe-Cu)2+) DMF/H of2After adding 350. mu. mol/L of anion to O (1/9, v/v, Tris 10mmol/L, pH 7.1) system (F)-，Br-，I-，SCN-，PO4 3-，PPi,S2O3 2-，H2PO4 -，HPO4 2-，N3 -，SO3 2-， AcO-，SO4 2-，NO2 -，CO3 2-，HCO3 -,S2-，CN-) FIG. 11 shows the change of the fluorescence spectrum detected after 30 min. As can be seen from FIG. 11, PPi enables the relay type multifunctional fluorescent probe-Cu2+The fluorescence emission of the probe is enhanced, which shows that the relay type multifunctional fluorescent probe-Cu2+The system is highly selective for PPi.
10 μmol/L N- (2- (2' -benzothiazolyl) phenyl) picolinamide and Cu2+Complex formed after action (fluorescent probe-Cu)2+) DMF/H of2FIG. 12 shows the change of fluorescence spectra measured when 0. mu. mol/L to 350. mu. mol/L of PPi pyrophosphate was added to O (1/9, v/v, Tris 10mmol/L, pH 7.1). As can be seen from FIG. 12, the fluorescence intensity of the emission peak at 557nm increased with increasing concentration of PPi, and was saturated when 350. mu. mol/L of PPi was added, and the fluorescence intensity did not change any more.
10 μmol/L N- (2- (2' -benzothiazolyl) phenyl) picolinamide and Cu2+Complex formed after action (fluorescent probe-Cu)2+) DMF/H of2After addition of 350. mu. mol/L of other anions and PPi to O (1/9, v/v, Tris 10mmol/L, pH 7.1), the fluorescence spectrum was measured as shown in the black bar portion of FIG. 13, with only PPi being able to cause a change in fluorescence. However, on this basis (addition of the other anion) a further 35 times the amount of PPi caused an increase in fluorescence, as indicated by the white striped portion in FIG. 13, indicating that the co-presence of other anions in the solution did not alter the probe molecules and Cu2+Selectivity of the complex formed after the action on PPi.
Based on SNR method, complex (fluorescent probe-Cu)2+) The limit of detection (LOD 3 σ/k, σ is the standard deviation of the blank solution; k is the slope of the calibration curve) was calculated to be 4.7 × 10-6mol/L。
The foregoing is only a preferred embodiment of the invention. It should be noted that, for those skilled in the art, the present invention is not limited thereto, and several modifications and decorations can be made without departing from the technical solution of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (8)
1. A preparation method of a relay type multifunctional fluorescent probe is characterized by comprising the following steps:
the relay type multifunctional fluorescent probe has the following structural formula:
the preparation method of the fluorescent probe comprises the following steps:
weighing 0.185g of 2-picolinic acid, dissolving the 2-picolinic acid in 15mL of dry dichloromethane, adding 0.682g of benzotriazole-N, N, N ', N ' -tetramethylurea hexafluorophosphate, stirring for 30 minutes, then adding 0.226g of 2- (2 ' -aminophenyl) benzothiazole and 0.181g of triethylamine, and stirring for reaction at room temperature; and (3) after the reaction is finished, evaporating the solvent under reduced pressure, and separating the residue by column chromatography to obtain the compound.
2. The method for preparing a relay type multifunctional fluorescent probe as claimed in claim 1, wherein the room temperature reaction temperature is 25 ℃ and the room temperature reaction time is 12 h.
3. The method for preparing the relay type multifunctional fluorescent probe as claimed in claim 1, wherein the eluent for column chromatography is ethyl acetate and petroleum ether in a volume ratio of 1: 10.
4. The application of the relay type multifunctional fluorescent probe as claimed in claim 1, which is characterized by application in detection and tracing of copper ions and pyrophosphate in a water environment system.
5. The application of the relay type multifunctional fluorescent probe is characterized in that the relay type multifunctional fluorescent probe has the following structural formula:
the relay type multifunctional fluorescent probe is prepared by mixing DMF (dimethyl formamide) and H (hydrogen peroxide) at a pH of 7.1 and a volume ratio of 1:92And detecting copper ions under a Tris buffer solution system of 10mmol/L of O.
6. The application of the relay type multifunctional fluorescent probe as claimed in claim 5, wherein 10 μmol/L Tris buffer solution of the relay type multifunctional fluorescent probe is added into a detected water sample, and fluorescence quenching can occur, indicating that the probe contains copper ions.
7. The application of the relay-type multifunctional fluorescent probe as claimed in claim 5, wherein the relay-type multifunctional fluorescent probe is prepared by mixing DMF and H at a pH of 7.1 and a volume ratio of 1:92Detecting copper ions in a Tris buffer solution system of 10mmol/L of O, quenching fluorescence, and continuously identifying pyrophosphate in the system.
8. The application of the relay-type multifunctional fluorescent probe as claimed in claim 7, wherein Tris buffer solution of the relay-type multifunctional fluorescent probe after detection and fluorescence quenching of copper ions is added into a detected water sample, and pyrophosphate is contained if fluorescence emission is enhanced.
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| CN104592983A (en) * | 2014-11-28 | 2015-05-06 | 渤海大学 | Fluorescent probes based on pyrene, and preparation method and application thereof |
| CN106770133A (en) * | 2017-01-19 | 2017-05-31 | 陕西师范大学 | One kind continuously detects Cu using aggregation-induced emission type fluorescence sense molecule2+With the method for pyrophosphate |
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| CN104592983A (en) * | 2014-11-28 | 2015-05-06 | 渤海大学 | Fluorescent probes based on pyrene, and preparation method and application thereof |
| CN106770133A (en) * | 2017-01-19 | 2017-05-31 | 陕西师范大学 | One kind continuously detects Cu using aggregation-induced emission type fluorescence sense molecule2+With the method for pyrophosphate |
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