CN110078666A - A kind of nickel ion fluorescence probe based on naphthalimide, preparation method and applications - Google Patents
A kind of nickel ion fluorescence probe based on naphthalimide, preparation method and applications Download PDFInfo
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- CN110078666A CN110078666A CN201910518386.8A CN201910518386A CN110078666A CN 110078666 A CN110078666 A CN 110078666A CN 201910518386 A CN201910518386 A CN 201910518386A CN 110078666 A CN110078666 A CN 110078666A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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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"
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- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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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 kind of nickel ion fluorescence probe and preparation method thereof based on naphthalimide, preparation method includes the following steps: 4- morpholine base -1,8- naphthalic anhydride, hydroxylamine hydrochloride and sodium bicarbonate mix at room temperature, ethyl alcohol is added, reflux, after the reaction was completed, it is evaporated in vacuo and is dried to obtain orange solids product.Its application is also disclosed.Nickel ion fluorescence probe prepared by the present invention based on naphthalimide is able to detect the Ni in other ions2+Ion.
Description
Technical field
The present invention relates to the detection technique field of toxic metal ions more particularly to a kind of nickel ions based on naphthalimide
The preparation method and applications of fluorescence probe.
Background technique
In recent years, organic molecule causes extensive pass to the detection of toxic metal ions as fluorescence chemical sensor
Note.These sensors are applied to biomedical and environmental science.Compared with other recognition methods, organic sensor it is main excellent
Point is synthesis simple, high sensitivity, at low cost.To Fe3+、Mn2+、Zn2+、Cu2+、Hg2+、Pb2+Detection report more than to nickel from
The detection of son.Ni2+It is essential microelement in the bioprocess such as breathing, biosynthesis, metabolism.Nickel is the important of human body
Element.Under normal circumstances, the nickel content in human body is very small.Such as adult body includes about 10 milligrams of nickel, normal blood
Middle concentration is g/ milliliters of 0.11 μ.Scarce nickel can lead to diabetes, anaemia, cirrhosis, uremia, renal failure and blood lipid and
Phospholipid metabolism is abnormal.Nickel is also the most common sensitization metal, and about 20% people is to nickel ion allergy [23-27].Female in allergic human population
Property patient quantity be higher than male patient.Nickel ion can enter skin by pore and sebaceous glands, cause skin with after human contact
Skin stimulation.Given this, it is intended to obtain a kind of efficient fluorescence probe, can be highly selective, highly sensitive detect Ni2+
Ion.
Naphthalimide fluorogen have good photostability, high-fluorescence quantum yield, biggish stoke shift and
Molecular structure is easy to the advantages that modifying, and is widely used in fluorescence probe field.Inspection of the naphthalimide to metal ion
Survey relates generally to Fe3+、Zn2+、Hg2+And Pb2+.And the fluorescent chemicals based on naphthalimide how are designed and synthesized for Ni2+
Detection be the problem to be solved in the present invention.
Summary of the invention
In order to solve the above-mentioned technical problem, the object of the present invention is to provide a kind of, and the nickel ion fluorescence based on naphthalimide is visited
The preparation method of needle is somebody's turn to do the nickel ion fluorescence probe based on naphthalimide and is able to detect the Ni in other ions2+Ion.
In order to solve the above technical problems, the present invention adopts the following technical scheme:
A kind of nickel ion fluorescence probe based on naphthalimide, structural formula are as follows:
。
A kind of preparation method of the nickel ion fluorescence probe based on naphthalimide, includes the following steps:
At room temperature by 4- morpholine base -1,8- naphthalic anhydride (CAS No.31837-36-2), hydroxylamine hydrochloride and sodium bicarbonate
Mixing, is added ethyl alcohol, and reflux, after the reaction was completed, vacuum evaporation are dried to obtain orange solids product；
Its reaction equation is as follows:
。
Further, the dosage quality of 4- morpholine base -1,8- naphthalic anhydride, hydroxylamine hydrochloride and sodium bicarbonate
Than: 800-900:280-240:200-300.
Further, the dosage quality of 4- morpholine base -1,8- naphthalic anhydride, hydroxylamine hydrochloride and sodium bicarbonate
Than: 849:209:252.
Further, the dosage of the ethyl alcohol is every 1000g4- morpholine base -1,8- naphthalic anhydride 20-27ml second
Alcohol.
Further, being evaporated in vacuo dry temperature is 35 DEG C.
The present invention also provides above-mentioned, and the nickel ion fluorescence probe based on naphthalimide detects Ni in other metal ions2+
The application of ion.
Compared with prior art, advantageous effects of the invention:
Probe and the combination with high priority of other metal ions of the invention, can be used for Ni in other metal ions2+Ion
Detection, be a kind of good fluorescence chemical sensor.
Detailed description of the invention
The invention will be further described for explanation with reference to the accompanying drawing.
Fig. 1 is in probe (10 of the invention-5M DMSO-H)2Exist in O (1:1) solution or there is no following ions
When ultraviolet-visible absorption spectroscopy: Probe, Na+,K+,Ca2+,Cr3+,Al3+,Fe3+,Fe2+,Mn2+,Cu2+,
Co2+,n2+,Ag+,Pb2+,and Ni2+(5ep)；
Fig. 2 is probe (10 of the invention-5M DMSO-H)2Ni is gradually increased in O (1:1) solution2+Purple when four times of amounts
Outer visible absorption spectra；
Fig. 3 is by 1:1 combination Ni2+Ultraviolet-visible absorption spectroscopy when ion；
Fig. 4 is probe (10 of the invention-5M DMSO-H)2Fluorescence when in O (1:1) solution presence or absence of following ion
Spectrum: Na+,K+,Ca2+,Cr3+,Al3+,Fe3+,Fe2+,Mn2+,Cu2+,Co2+,Zn2+,Ag+,Pb2+,and
Ni2+(10ep)；
Fig. 5 is probe (10 of the invention-5M DMSO-H)2Ni is gradually increased in O (1:1) solution2+Fluorescence spectrum when ion
Variation；
Fig. 6 is the fluorescence intensity at probe 550nnm of the invention with Ni2+The variation diagram of ion concentration (0-5.0ep)；
Fig. 7 is probe (10 of the invention-5M DMSO-H)2Presence or absence of Na in O (1:1) solution2Fluorescence light when EDTA
It composes (0-1ep)；
Fig. 8 is that Na is added2After EDTA (0-2ep), the fluorescence intensity change value of probe of the invention at 550nm and addition
Na2Concentration (0to1ep) linear accompanying drawings of EDTA；
The dark probe (10 for invention in Fig. 9-5M DMSO-H)2When in O (1:1) solution presence or absence of following ion
Fluorescence spectrum: Na+,K+,Ca2+,Cr3+,Al3+,Fe3+,Fe2+,Mn2+,Cu2+,Co2+,Zn2+,Ag+,Pb2+, and Ni2+(10ep) with
And by Ni2+(1ep) is added to the schematic diagram in above-mentioned solution；
Figure 10 is probe (10 of the invention-5M DMSO-H)2There are fluorescence spectrums when different nickel salts in O (1:1) solution.
Specific embodiment
A kind of preparation method of the nickel ion fluorescence probe based on naphthalimide, by 4- morpholine base -1,8- naphthalenedicarboxylic acid
Acid anhydride (0.849g, 3mmol), hydroxylamine hydrochloride (0.209g, 3mmol) and sodium bicarbonate (0.252g, 3mmol) mix at room temperature
It closes, is added ethyl alcohol (20ml), flow back 2 h, and after the reaction was completed, vacuum evaporation is dried to obtain orange solids product and (is named as
Probe).
No. CAS of 4- morpholine base -1,8- naphthalic anhydride used in the present invention is No.31837-36-2.
Its reaction equation is as follows:
。
Chromatogram purification is then carried out on a silica gel column, obtains orange product (0.801g), yield 90%.1H NMR (400
MHz, DMSO-d6)δ= 10.64 (s,1H), 8.55–8.47 (m, 2H), 8.43 (d,J=8.1 Hz, 1H), 7.83
(dd, J=8.3 Hz, 7.5 Hz, 1H), 7.37 (d,J=8.1 Hz, 1H), 3.96–3.88 (m, 4H), 3.27–
3.20 (m, 4H). 13C NMR (100 MHz, DMSO-d6)δ= 161.36, 161.02, 156.19,132.80,
131.27,128.47,126.70,125.86,123.33,116.45,115.70,66.64, 53.54。ESI-HRMS
(C16H14N2O4): calcd[M+H]+: 299.1032, obtained:299.1800。
The dissolved metal ions in the distilled water that pH value is 7.00 have carried out the metal sensor experiment based on Probe.It will
The DMSO-H of Probe2O (1:1) solution is mixed with deionized water solution, is evaluated its sensing capabilities.Two kinds of solution are mixed
After conjunction, detect by an unaided eye its colorimetric properties, and carries out quantitative analysis with UV-Vis Spectrophotometry.All experiments are in room
Temperature is lower to be carried out.
1, uv-visible absorption spectra is studied
It is probe (10 as shown in figure Fig. 1-5M) in 5.0 eq. different metal ions in DMSO-H2Purple in O (1:1) solution
Outside-visible spectrum.Probe has wider absorption spectrum at 400 nm at room temperature.With the addition of different metal ions, inhale
Spectrum is received to be changed.Ni is added2+After ion, absorption spectrum becomes red, occurs new absorption spectrum at 470 nm.With
Ni2+The increase (0-4ep) of concentration, UV absorption intensity is gradually increased (Fig. 2) at 470 nm.From figure 3, it can be seen that probe with
Ni2+Combination ratio be 1:1.In ESI-MS analysis, 425.2399 (Probe+NiCl2- 1) peak value further demonstrates this
A bit.This variation that visual field absorbs is possibly realized using colorimetric method from yellow to orange detection nickel ion.
2, fluorescence spectrum is studied
Probe and different cation (Na are had studied using fluorescent spectrometry+、K+、Ca2+、Cr3+、Al3+、Fe3+、Fe2+、Mn2+、
Cu2+、Co2+、Zn2+、Ag+、Pb2+、Ni2+) bonding behavior, and further evaluation Probe to the selectivity of nickel ion.With other
Metal ion is compared, and nickel ion has apparent fluorescent quenching (Fig. 4).Visually after visible addition nickel ion color by yellowish green discoloration
For dark brown.As shown in figure 5, with Ni2+The increase of concentration, the fluorescence intensity at 550nm gradually decreases, until being quenched completely.
From fig. 6, it can be seen that fluorescence intensity and Ni2+Ion concentration is in negative linear correlation (R within the scope of 0-1.0 ep2=0.98631)。
But addition Na+、K+、Ca2+、Cr3+、Al3+、Fe3+、Fe2+、Mn2+、Cu2+、Co2+、Zn2+、Ag+、Pb2+Equal metal ions are to probe
Fluorescence has no significant effect, and illustrates Probe to Ni2+It is sensitive.The strong quenching of this initial fluorescence is Probe and Ni2+Between formed
Coordination complex, to promote excited energy transfer or electric charge transfer.
3, probe is to Ni2+The sensor mechanism of ion
By the reversible experiment, detection mechanism is illustrated.As shown in fig. 7, Na is added2After EDTA (0-1.0 ep), in 550nm
Locate Ni2+The fluorescence intensity that system is quenched gradually increases and restores.This is because EDTA can be with Ni2+Ion formed complex from
And release fluorescent molecule.From figure 8, it is seen that fluorescence intensity is linearly positively correlated within the scope of 0-1.0 ep with EDTA concentration
(R2=0.99059).From1 H NMR can be seen that addition NiCl2Afterwards, the chemical shift of hydrogen changes on Probe hydroxyl, this
The binding site for showing nickel ion is the oxygen on hydroxyl oxygen and C=O on probe.
4, probe is to Ni2+With the tournament selection of other metal ions
The possible interference of other metal ions is further had rated by competitive assay.With the probe solution phase containing only nickel ion
Than containing Ni2+The fluorescence intensity of ion and other metal ion probe solutions is without significant change (Fig. 9).These are the result shows that probe
With the combination with high priority of other metal ions.Probe can be used for Ni in other metal ions2+The detection of ion is a kind of
Good fluorescence chemical sensor.In addition, in order to study anion to probe to Ni2+The influence of the sensing behavior of ion, research
Fluorescence reaction of the probe to the acetate of nickel, chloride and sulfate.From fig. 10 it can be seen that probe is to NiSO4、NiCl2、
Ni(CH3COO)2Fluorescence response without significant change.
Embodiment described above is only that preferred embodiment of the invention is described, and is not carried out to the scope of the present invention
It limits, without departing from the spirit of the design of the present invention, those of ordinary skill in the art make technical solution of the present invention
Various changes and improvements, should all fall into claims of the present invention determine protection scope in.
Claims (8)
1. a kind of nickel ion fluorescence probe based on naphthalimide, it is characterised in that: its structural formula is as follows:
。
2. the preparation method of the nickel ion fluorescence probe according to claim 1 based on naphthalimide, it is characterised in that: packet
Include following steps:
4- morpholine base -1,8- naphthalic anhydride, hydroxylamine hydrochloride and sodium bicarbonate are mixed at room temperature, ethyl alcohol is added, is flowed back,
After the reaction was completed, it is evaporated in vacuo and is dried to obtain orange solids product；
Its reaction equation is as follows:
。
3. preparation method according to claim 2, it is characterised in that: 4- morpholine base -1,8- naphthalic anhydride, salt
The dosage mass ratio of sour azanol and sodium bicarbonate: 800-900:280-240:200-300.
4. preparation method according to claim 2, it is characterised in that: 4- morpholine base -1,8- naphthalic anhydride, salt
The dosage mass ratio of sour azanol and sodium bicarbonate: 849:209:252.
5. preparation method according to claim 2, it is characterised in that: the dosage of the ethyl alcohol is every 1000g4- morpholine
Base -1,8- naphthalic anhydride 20-27ml ethyl alcohol.
6. preparation method according to claim 2, it is characterised in that: being evaporated in vacuo dry temperature is 35 DEG C.
7. the nickel ion fluorescence probe according to claim 1 based on naphthalimide detects Ni in other metal ions2+
The application of ion.
8. the nickel ion fluorescence probe based on naphthalimide prepared according to preparation method described in claim 2-6 any one
Ni is detected in other metal ions2+The application of ion.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114702505A (en) * | 2022-04-26 | 2022-07-05 | 鄂尔多斯应用技术学院 | Fluorescent probe molecule for nickel ion recognition and preparation method and application thereof |
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|---|---|---|---|---|
| WO1998019648A2 (en) * | 1996-11-01 | 1998-05-14 | Warner-Lambert Company | N-oxy-naphthalimides as antibacterial agents |
| CN107253932A (en) * | 2017-05-26 | 2017-10-17 | 济南大学 | A kind of quick high-selectivity hypersensitive nickel ion ratio fluorescent probe and preparation method thereof |
| CN107987824A (en) * | 2017-12-09 | 2018-05-04 | 福建医科大学 | Ag in one kind identification A549+Naphthoyl imide compounds fluorescence probe and preparation method thereof |
-
2019
- 2019-06-15 CN CN201910518386.8A patent/CN110078666B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998019648A2 (en) * | 1996-11-01 | 1998-05-14 | Warner-Lambert Company | N-oxy-naphthalimides as antibacterial agents |
| CN107253932A (en) * | 2017-05-26 | 2017-10-17 | 济南大学 | A kind of quick high-selectivity hypersensitive nickel ion ratio fluorescent probe and preparation method thereof |
| CN107987824A (en) * | 2017-12-09 | 2018-05-04 | 福建医科大学 | Ag in one kind identification A549+Naphthoyl imide compounds fluorescence probe and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 矫春鹏，等: "检测活性氮/活性氧的分子荧光探针", 《有机化学》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114702505A (en) * | 2022-04-26 | 2022-07-05 | 鄂尔多斯应用技术学院 | Fluorescent probe molecule for nickel ion recognition and preparation method and application thereof |
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