CN106928141A - Tetraphenyl ethylene schiff bases feux rouges zinc ion probe and preparation method and purposes - Google Patents
Tetraphenyl ethylene schiff bases feux rouges zinc ion probe and preparation method and purposes Download PDFInfo
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- CN106928141A CN106928141A CN201710135796.5A CN201710135796A CN106928141A CN 106928141 A CN106928141 A CN 106928141A CN 201710135796 A CN201710135796 A CN 201710135796A CN 106928141 A CN106928141 A CN 106928141A
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- zinc ion
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
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- 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
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- 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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Abstract
The invention discloses a kind of tetraphenyl ethylene schiff bases feux rouges zinc ion probe and preparation method thereof and purposes, the compound synthesis method is simple, and abbreviation HL, its chemical structural formula is shown below.The probe can be used for detection zinc ion and with sensitivity higher, and detection line can reach 9 × 10‑8.Experiment is proved：Zinc ion fluorescent of the invention in selective enumeration method zinc ion and can occur fluorescein and move and strengthen, and mark zinc ion field to have potential application value in living things system.
Description
Technical field
The present invention relates to a kind of feux rouges fluorescence probe of quick detection zinc ion, specifically a kind of tetraphenyl ethylene schiff bases
Feux rouges zinc ion probe and preparation method thereof, belongs to technical field of analytical chemistry.
Background technology
Zinc ion is the transition metal of the second enrichment in human body, is distributed widely in inside of human body.For example, in adult human body altogether
Containing 2.3g zinc, and the content of copper is only 250mg.It is furthermore interesting that, substantial amounts of zinc ion is present in nerve fiber, such as in brain
The concentration of zinc ion has reached 0.1-0.5mM in tissue.At present it is known that the number in enzyme of its activated centre comprising zinc ion surpasses
1000 kinds are crossed, there is zinc ion in six big fermentoids, zinc ion take part in all metabolic processes of cell.
A large amount of evidences inside and outside organism all show that zinc ion is a kind of important adjustment element in apoptosis process.
Zinc ion can be discharged from cynapse capsule and enter cell by electric potential regulating type calcium ion channel, this show Free Zinc from
Son also has dysfunction of nervous regulation.Additionally, the disorder of zinc ion metabolism can also cause many diseases, such as Alzheimer
Family name's disease, amyotrophic lateral sclerosis (spinal cord) lateral sclerosis, epilepsy and Parkinson's disease etc..
However, because zinc ion is not free d tracks, so being jumped without the d-d electronics that transition metal generally has
Move, in visible region, zinc enzyme does not have visible spectrum yet.Simultaneously because zinc ion does not exist not paired electronics, so
Any magnetic signal is not showed, therefore utilizes conventional method of analysis, such as ultraviolet visible spectrometry, nuclear magnetic resonance method or electron paramagnetic yet
Resonance method can not effectively detect this atypical metal ion in vivo, and this gives people the research band of internal zinc ion
Difficulty is necessarily carried out.Zinc ion detection technique of fluorescence developed in recent years is to complete the studies above to work most strong
One of means.
At present the zinc ion fluorescent reported be mostly based on traditional fluorescent chromophore for example naphthalimide, cumarin,
Rhodamine etc., detects zinc ion, largely by probe in itself by the single enhancing of fluorescent quenching or fluorescence intensity
Spectrum and instrument performance are disturbed.
The content of the invention
For the problems of current zinc ion fluorescent detection and defect, the present invention is by MOLECULE DESIGN, synthesis
Go out a kind of tetraphenyl ethylene schiff bases feux rouges zinc ion probe, while giving the preparation method and its usage of the probe.By zinc
Ion coordination, hinders probe energy transfer in itself, causes launch wavelength to change, and detection line can reach 9 × 10-8M, with height
Sensitivity.
Tetraphenyl ethylene schiff bases feux rouges zinc ion probe (HL) of the present invention, molecular structural formula is as follows：
Molecular formula is：C36H26N2O。
The synthetic route of tetraphenyl ethylene schiff bases feux rouges zinc ion probe (HL) of the present invention is as follows：
The synthesis of tetraphenyl ethylene schiff bases feux rouges zinc ion probe of the present invention can be carried out by the following steps：
1) diphenyl-methane (1eq) is dissolved in tetrahydrofuran (THF), keeps subzero 20 DEG C, under nitrogen protective condition, slow drop
Plus n-BuLi (1eq), after 30min, 4- methoxy benzophenones (1eq) is added dropwise, it is stirred at room temperature 3 hours, add water and be quenched, two
Chloromethanes (DCM) is extracted, and screws out solvent, adds toluene, adds p-methyl benzenesulfonic acid (0.1eq), is flowed back 6 hours, is cooled to room temperature,
Column chromatography obtains compound A.
2) compound A (1eq) is dissolved in acetic acid, adds 48% hydrobromic acid (10eq), flowed back 24 hours, after column chromatography
Obtain compound B.
3) compound B-11 eq) acetic acid is dissolved in, add hexamethylenetetramine (10eq) backflow 6h, the compound C of column chromatography.
4) compound C (1eq) is dissolved in ethanol, adds 8- aminoquinolines (1eq), titrates a few drop glacial acetic acids, recrystallizing methanol
Obtain compound HL.
The purposes of zinc ion probe of the present invention：The fluorescence probe can apply the fluorescence sense of zinc ion to detect.
Advantages of the present invention：(1) the synthesis cost of probe is than relatively low, and last handling process is relatively easy；(2) present invention is real
Show the selective quick detection of zinc ion, and it is selective good, resist other molecule interference performances strong.
Therefore, in the presence of zinc ion, the fluorescence probe can rapidly occur ripple by the stimulation of ultraviolet lighting
Red shift long and the increase of fluorescence intensity, are preferably used for the detection of zinc ion.Probe of the present invention has larger Stokes displacements,
Luminous zone has reached red light region, and close to near-infrared wavelength, compared with probe in itself blue light wavelength, signal to noise ratio is substantially reduced, and makes
Must detect that zinc ion is more definite.So, the present invention is a kind of simple, and quickly, the zinc ion specific detection with feux rouges is tried
Agent, has broad application prospects in biological ion detection field.Its performance will give specifically in embodiment with reference to accompanying drawing
It is bright.
Brief description of the drawings
Fig. 1 is tetraphenyl ethylene schiff bases feux rouges zinc ion probe HL of the present invention in embodiment1H NMR spectras.
Fig. 2 is changes of the tetraphenyl ethylene schiff bases feux rouges zinc ion probe HL of the present invention with the addition fluorogram of zinc ion
Situation.
Fig. 3 is the change that tetraphenyl ethylene schiff bases feux rouges zinc ion probe HL of the present invention increases fluorogram with zinc ion concentration
Change situation.
Fig. 4 is fluorescence intensity after tetraphenyl ethylene schiff bases feux rouges zinc ion probe HL of the present invention is added to different metal ions
Situation of change.
Fig. 5 is recognition mechanism collection of illustrative plates of the tetraphenyl ethylene schiff bases feux rouges zinc ion probe HL of the present invention to zinc ion.
Fig. 6 is recognition mechanism nuclear-magnetism proof diagrams of the tetraphenyl ethylene schiff bases feux rouges zinc ion probe HL of the present invention to zinc ion
Spectrum.
Fig. 7 is detection line collection of illustrative plates of the tetraphenyl ethylene schiff bases feux rouges zinc ion probe HL of the present invention to zinc ion.
Specific embodiment
With reference to embodiment and accompanying drawing, the present invention will be further described, but the present invention is not limited by following embodiments
System, number of the number of compound for compound in such scheme in embodiment.
Embodiment
The synthesis of tetraphenyl ethylene schiff bases feux rouges zinc ion probe compound HL proposed by the present invention
The synthetic route of compound HL is as follows：
1st, the synthesis of compound A：
Diphenyl-methane (12mmol, 2.02g) is dissolved in 50ml tetrahydrofurans, subzero 20 DEG C, under nitrogen protection, 2.5M is added dropwise
N-BuLi (10mmol, 4ml), is added dropwise 4- methoxy benzophenones (12mmol, 3.03g) and is warmed up to room temperature, stirs 3 hours,
Add water and be quenched, dichloromethane extraction screws out solvent, add toluene, p-methyl benzenesulfonic acid (1.8mmol, 0.342g) to flow back 6 hours,
Cooling room temperature, 5% sodium acid carbonate is washed twice, and anhydrous magnesium sulfate is bold enough to do, and screws out solvent, obtains yellow crude product, is recrystallized
White solid product compound A, rate 80%.1H NMR(400MHz,DMSO-d6)δ(TMS,ppm)：7.19-7.06(m,9H),
7.03-6.92 (m, 6H), 6.87 (d, J=8.7Hz, 2H), 6.70 (d, J=8.8Hz, 2H), 3.67 (s, 3H).
2nd, the synthesis of compound B：
Compound A (4.4mmol, 1.72g), is dissolved in glacial acetic acid, adds 48% hydrobromic acid (50ml), is refluxed 12 small
When, solvent is evaporated off, add toluene to steam again, ethyl acetate extraction, respectively with sodium acid carbonate, saturated common salt is washed twice, anhydrous sulphur
Sour magnesium is dried, and screws out solvent, column chromatography (n-hexane/ethyl acetate=10:1) product Compound B is obtained.1H NMR(400MHz,
CDCl3) δ (TMS, ppm) 7.16-7.10 (m, 9H), 7.08-7.02 (m, 6H), 6.92 (d, J=8.3Hz, 2H), 6.59 (d, J
=8.3Hz, 2H), 4.61 (s, 1H).
3rd, the synthesis of compound C：
Compound B (1.0g, 3mmol) is dissolved in 50ml glacial acetic acids, hexamethylenetetramine (4.2g, 30mmol) is added,
Backflow 3 hours, after reaction completely, is extracted 2 times with dichloromethane, is washed 2-3 times, and salt is washed 1 time, and anhydrous sodium sulfate drying subtracts
Pressure obtains crude product, column chromatography (methylene chloride/methanol=50 after being spin-dried for solvent:1) compound C is obtained, yield is 70%.1H NMR
(400MHz,DMSO-d6)δ(TMS,ppm):10.70 (s, 1H), 10.11 (s, 1H), 7.23 (d, J=2.4Hz, 1H), 7.20-
7.07 (m, 10H), 7.01-6.94 (m, 6H), 6.75 (d, J=8.6Hz, 1H).
4th, the synthesis of compound HL：
Compound C (0.376g, 1mmol) and 8- aminoquinolines (0.30g, 1mmol) are dissolved in ethanol, are added dropwise 1 and drip glacial acetic acid,
Backflow overnight, separates out solid, recrystallizes to obtain compound HL.Yield 90%.1H NMR(400MHz,DMSO-d6)δ(TMS,ppm):
14.07 (s, 1H), 8.89 (s, 1H), 8.43 (d, J=8.3Hz, 1H), 7.91 (d, J=7.9Hz, 1H), 7.73-7.55 (m,
3H), 7.27 (d, J=2.3Hz, 1H), 7.15 (m, J=19.5,8.4Hz, 9H), 7.08-6.97 (m, 8H), 6.75 (d, J=
8.5Hz, 1H), nuclear magnetic spectrogram is as shown in Figure 1.
Tetraphenyl ethylene schiff bases feux rouges zinc ion probe compound HL of the present invention adds the increase fluorescence of equivalent with zinc ion
The change of spectrogram：
Take tetraphenyl ethylene schiff bases feux rouges zinc ion probe compound HL manufactured in the present embodiment and be dissolved in tetrahydrofuran (THF)
In, it is made 1mmol/L storing solutions.20uL is taken out from storing solution to be added in the middle of the centrifuge tube of 5mL, and 4mL is diluted to THF,
The zinc ion standard liquid of different equivalents (0-2.0eq) is added, its photoluminescent property is measured.Fluorescence spectrum as shown in Figures 2 and 3, is sent out
Light mechanism and nucleus magnetic hydrogen spectrum are shown in Figure 4 and 5 respectively as the spectrogram that zinc ion is added changes.
Selectivity of the tetraphenyl ethylene schiff bases feux rouges zinc ion probe compound HL of the present invention to different metal ions：
20 μ L are taken out from foregoing storing solution to be added in the middle of the centrifuge tube of 5mL, are separately added into the competition point of equimolar amounts
Substandard solution, zinc ion standard liquid [(1) blank of one of addition equimolar amounts；(2) zinc ion；(3)Cd2+；(4)
Mg2+；(5)Ag+；(6)Co2+；(7)Mn2+；(8)Ni2+；(9)Cu2+；(10)K+；(11)Ba2+；(12)Na+], with THF after 30min
It is solvent, 365nm is exciting light, detects the fluorescence emission spectrum change of solution, as a result as shown in Figure 6.It is investigated it simultaneously
His influence of the metal ion to fluorescence probe intensity of the present invention, with THF as solvent, 365nm is exciting light.Being seen by Fig. 6 can be with
It was found that, fluorescence of other metal ions to compound HL at 600nm has little to no effect, and the making of addition of zinc ion solution
Fluorescence of the compound HL at 600nm is significantly increased.
In summary experimental data, probe of the present invention has single-minded selectivity to zinc ion, while there is high sensitivity, most
Low detection property can reach 9 × 10-8M (Fig. 7).Probe identification zinc ion emission wavelength is 600nm, is red light region, close to closely
Region of ultra-red, applies the zinc ion in life system to recognize there is very big development potentiality after being.
Claims (3)
1. a kind of tetraphenyl ethylene schiff bases feux rouges zinc ion probe, its molecular structural formula is as follows：
2. a kind of preparation method of the tetraphenyl ethylene schiff bases feux rouges zinc ion probe described in claim 1, its step is as follows：
Step 1, diphenyl-methane 1eq are dissolved in tetrahydrofuran, keep subzero 20 DEG C, under nitrogen protective condition, n-BuLi are added dropwise
After 1eq, 30min, 4- methoxy benzophenone 1eq are added dropwise, are stirred at room temperature 3 hours, add water and be quenched, dichloromethane (DCM) extraction
Take, screw out solvent, add toluene, add p-methyl benzenesulfonic acid 0.1eq, flow back 6 hours, be cooled to room temperature, column chromatography obtains compound
A：
Step 2, compound A 1eq are dissolved in acetic acid, add 48% hydrobromic acid 10eq, flowed back 24 hours, after column chromatography
Compound B：
Step 3, compound B 1eq are dissolved in acetic acid, add hexamethylenetetramine 10eq, flow back 6 hours, the compound C of column chromatography：
Step 4, compound C 1eq are dissolved in ethanol, add 8- aminoquinoline 1eq, titrate glacial acetic acid, and recrystallizing methanol obtains compound
HL。
3. the tetraphenyl ethylene schiff bases probe described in claim 1 is used for the fluoroscopic examination of zinc ion.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108424349A (en) * | 2018-03-29 | 2018-08-21 | 山东大学 | A kind of preparation method of the rare earth nano line for the tetraphenyl ethylene Derivatives Modified can be used for organic carboxyl acid detection |
| CN108593608A (en) * | 2018-02-08 | 2018-09-28 | 陕西师范大学 | Tetraphenyl ethylene pyridiniujm is in detection NO3-And ClO4-In application |
| CN110467570A (en) * | 2019-08-30 | 2019-11-19 | 广东工业大学 | A kind of tetraphenyl ethylene -8-hydroxyquinoline class compound and its preparation method and application |
| CN110746374A (en) * | 2019-12-11 | 2020-02-04 | 南通大学 | Tetrastyrene Schiff base Zn2+Fluorescent probe and preparation method and application thereof |
| CN111440281A (en) * | 2020-03-02 | 2020-07-24 | 华南理工大学 | Chiral Schiff base polymers and preparation method and application thereof |
| CN112209871A (en) * | 2020-10-29 | 2021-01-12 | 西北师范大学 | Zinc ion fluorescent probe based on tetraphenylethylene and preparation method and application thereof |
| CN114634507A (en) * | 2022-05-18 | 2022-06-17 | 烟台大学 | Fluorescent probe for detecting zinc ions and preparation method thereof |
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| ANKUR BIKASH PRADHAN等: ""A highly selective fluorescent sensor for zinc ion based on quinoline platform with potential applications for cell imaging studies"", 《POLYHEDRON》 * |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108593608A (en) * | 2018-02-08 | 2018-09-28 | 陕西师范大学 | Tetraphenyl ethylene pyridiniujm is in detection NO3-And ClO4-In application |
| CN108424349A (en) * | 2018-03-29 | 2018-08-21 | 山东大学 | A kind of preparation method of the rare earth nano line for the tetraphenyl ethylene Derivatives Modified can be used for organic carboxyl acid detection |
| CN108424349B (en) * | 2018-03-29 | 2020-05-12 | 山东大学 | Preparation method of tetraphenylethylene derivative modified rare earth nanowire for organic carboxylic acid detection |
| CN110467570A (en) * | 2019-08-30 | 2019-11-19 | 广东工业大学 | A kind of tetraphenyl ethylene -8-hydroxyquinoline class compound and its preparation method and application |
| CN110746374A (en) * | 2019-12-11 | 2020-02-04 | 南通大学 | Tetrastyrene Schiff base Zn2+Fluorescent probe and preparation method and application thereof |
| CN110746374B (en) * | 2019-12-11 | 2022-03-01 | 南通大学 | Tetrastyrene Schiff base Zn2+Fluorescent probe and preparation method and application thereof |
| CN111440281A (en) * | 2020-03-02 | 2020-07-24 | 华南理工大学 | Chiral Schiff base polymers and preparation method and application thereof |
| CN112209871A (en) * | 2020-10-29 | 2021-01-12 | 西北师范大学 | Zinc ion fluorescent probe based on tetraphenylethylene and preparation method and application thereof |
| CN114634507A (en) * | 2022-05-18 | 2022-06-17 | 烟台大学 | Fluorescent probe for detecting zinc ions and preparation method thereof |
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Application publication date: 20170707 |