CN107501179A - It is a kind of based on the water-soluble copper ion fluorescence probe material of naphthalimide dicarboxylic acids and its preparation and application - Google Patents
It is a kind of based on the water-soluble copper ion fluorescence probe material of naphthalimide dicarboxylic acids and its preparation and application Download PDFInfo
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Abstract
The invention discloses a kind of water-soluble copper ion fluorescence probe and preparation method thereof, belong to chemical synthesis and technical field of analytical chemistry.The water-soluble copper ion fluorescence probe of the present invention, chemistry are entitledN[the ethylenediamine 2 of normal-butyl 4N,N'Two (3 propionic acid)] 1,8 naphthalimides, its synthetic method is first to make 4 bromines 1, the amidatioon of 8 naphthalene anhydrides and n-butylamine, then the bromine for making ethylenediamine substitute 4, then carry out michael reaction with methyl acrylate, last alkaline hydrolysis, cation exchange column is crossed, obtains copper ion fluorescence probe.Experiment shows, the probe is in DMSO/HEPES buffer systems, simultaneously fluorescent quenching occurs for energy selective enumeration method copper ion, realization quantitatively detects copper ion, detection sensitivity is high, and identification is not disturbed by other ions, therefore, the detection of heavy metal ion, the detection of copper ion especially in biological tissue and environmental wastewater can be applied to as copper ion fluorescence probe.
Description
Technical field
The present invention relates to a kind of water-soluble copper ion fluorescence probe material, more particularly to one kind to be based on naphthalimide dicarboxylic acids
Water-soluble copper ion fluorescence probe material and preparation method thereof；The present invention also relates to the copper ion fluorescence probe high selection
The application of property fluorescence identifying copper ion, belongs to technical field of polymer materials and technical field of analytical chemistry.
Background technology
Copper is to be only second to iron and zinc in human body, the necessary trace element more than the 3rd, be take part in human body many basic
Physiology course, such as the function and structure reinforcing of protein, gene expression, nervous system.It is well known that copper serves as in life entity
The catalytic factor of a large amount of metalloenzyme, but Excess free enthalpy copper, can cause some neuropathic diseases, for example, Menkes and
Wilson diseases, familial amyotrophic lateral sclerosis, Alzheimer's disease and Prion diseases, in addition, minor's Excess free enthalpy
Copper, hepar damnification can be caused.Thus, it is to environmental protection and human health in environment and life vivo detection and monitoring copper ion
It is considerable.
The research of copper ion fluorescence probe has attracted the research interest of more and more researchers at present, has reported base
In copper ion fluorescence probes such as cumarin, rhodamine, two pyrroles's boranes and naphthalimides.However, these fluorescence probes are water-soluble
Property is poor, synthesis is complicated so that their application prospect is restricted.Therefore, research and develop a kind of good water solubility, have high selectivity and
The copper ion fluorescence probe of high sensitivity is highly desirable.
The content of the invention
It is an object of the invention to provide a kind of water-soluble copper ion fluorescence probe material based on naphthalimide dicarboxylic acids
Preparation method；
It is a further object of the present invention to provide a kind of answering for above-mentioned water-soluble copper ion fluorescence probe material fluorescence identifying copper ion
With；
It is a further aim of the invention a kind of above-mentioned water-soluble copper ion fluorescence probe material is provided in quantitative detecting analysis
The application of copper ion.
First, the preparation of water-soluble copper ion fluorescence probe material
The water-soluble copper ion fluorescence probe material of the present invention, is using naphthalimide as chromophore, and carboxyl is recognition group, and it is changed
Scientific name is referred to as：N- normal-butyl -4- [ethylenediamine -2-N,N'- two (3- propionic acid)] -1,8- naphthalimides（Abbreviation WP）, structural formula is such as
Under：
The preparation of water-soluble copper ion fluorescence probe material, comprises the following steps：
（1）The synthesis of the bromo- 1,8- naphthalimides of N- normal-butyls -4-：In ethanol, bromo- 1, the 8- naphthalene anhydrides of 4- flow back into n-butylamine
Row amidation process, cooling, solid is separated out, washed, dried, obtainNThe bromo- 1,8- naphthalimides of-normal-butyl -4-；
The mol ratio of the bromo- 1,8- naphthalene anhydrides of 4- and n-butylamine is 1:1~1:3；Amidation process temperature is 75 ~ 85 DEG C, and the reaction time is
3 ~ 4 hours.
（2）NThe synthesis of-normal-butyl -4- ethylenediamine -1,8- naphthalimides：Under condition of no solvent,N- normal-butyl -4- is bromo-
1,8- naphthalimide carries out substitution reaction with ethylenediamine, is cooled down after the completion of reaction, adds elutriation to go out precipitation, obtains intermediate productN- just
Butyl -4- ethylenediamine -1,8- naphthalimides；
NThe mol ratio of the bromo- 1,8- naphthalimides of-normal-butyl -4- and ethylenediamine is 1:60~1:70；The temperature of substitution reaction be 60 ~
70 DEG C, the reaction time is 3 ~ 4 hours.
（3）N- normal-butyl -4- [ethylenediamine -2-N,N'- bis- (3- methyl propionates)] -1,8- naphthalimides synthesis：First willN- normal-butyl -4- ethylenediamines -1,8- naphthalimide dissolves in methyl alcohol, adds excessive methyl acrylate, reaction is stirred at room temperature
11-13 days, yellow mercury oxide separated out, and filtered, and washing, obtainedN- normal-butyl -4- [ethylenediamine -2-N,N'- bis- (3- methyl propionates)]-
1,8- naphthalimides；
NIt is 1 that-normal-butyl -4- ethylenediamine -1,8- naphthalimides, which are dissolved with the mol ratio of methyl acrylate,:9~1:11.
（4）N- normal-butyl -4- [ethylenediamine -2-N,N'- two (3- propionic acid)] -1,8- naphthalimides synthesis：WillN- positive fourth
Base -4- [ethylenediamine -2-N,N'- bis- (3- methyl propionates)] -1,8- naphthalimides carry out alkaline hydrolysis with potassium hydroxide-methanol solution,
Concentration, the cationic ion exchange column of acid activation is crossed, concentration, obtains target productN- normal-butyl -4- [ethylenediamine -2-N,N'- two
(3- propionic acid)] -1,8- naphthalimides --- water-soluble copper ion fluorescence probe material.
The concentration of potassium hydroxide-methanol solution is 2-4 mol/Ls.The temperature that potassium hydroxide-methanol solution carries out alkaline hydrolysis is
70 ~ 80 DEG C, the time is 2 ~ 3 hours.
2nd, recognition performance of the probe material to copper ion
1st, identification of the probe to metal ion
To probe into recognition capability of the probe to metal ion, DMSO/HEPES cushioning liquid is selected（1:1 v/v）In to Na+, K+,
Ca2+, Mg2+, Al3+, Pb2+, Fe3+, Ni2+, Zn2+, Cu2+, Hg2+, Ag+, Co2+, Cr3+, Mn2+, Cd2+Detected.Add and fix
The concentration of probe material（1×10-3Mol/L, 10 μ L）, it is separately added into 100 μ L metal ions（1×10-3mol/L）, 2mLDMSO/
HEPES cushioning liquid（1:1 v/v, pH=7.4）, fixed excitation wavelength（435 nm）, record its fluorescence spectrum and map.
As a result find：When excitation wavelength is in 435nm, probe WP shows very strong glimmering at maximum emission wavelength 532nm
Light, after adding each metal ion species, only Cu2+Cause probe WP fluorescent quenching 75.41%（Reduce by 4.07 times）, and other gold
Category ion adds not to be responded significantly to WP fluorescence intensity（Without result in any significant change）.Illustrate WP to Cu2+Tool
There is high selectivity（See Fig. 1）.
2nd, interference free performance detects
In order to determine probe WP to Cu2+Detection results, we have carried out the detection of following interference free performance again：Keep probe WP
Concentration constant (1 × 10-3Mol/L, 10 μ L), add copper ion（1×10-3Mol/L, 100 μ L）With other metal ions（1×
10-3Mol/L, 100 μ L）, 1mLDMSO and 1mL HEPES, measure its fluorescence intensity（Ex 435 nm）.As a result find, add 14
After kind of cation, fluorescent quenchings of the probe WP at 532nm, this and Cu2+Influence to probe is consistent（See Fig. 2 fluorescence
Spectrum）.So as to illustrate that probe WP detects Cu2+Substantially do not disturbed by other cations, probe has high selectivity.
3rd, fluorescence titration
To the DMSO-HEPES (1 containing various concentrations copper ion:1 v/v) probe WP fluorescence titration has been carried out in solution.
Take probe WP（1×10-3mol/L）20 μ L, 1mLDMSO and 1mL HEPES（pH=7.4）It is added to 1 × 1 cm2Quartz cuvette
In ware, stir, add copper ion（0.4×10-3Mol/L, distilled water）0,5 μ L, 10 μ L, 15 μ L, 20 μ L ... 80 μ L and
Distilled water 80 μ L, 75 μ L, 70 μ L, 65 μ L, the 60 μ L ... 0 of various dose, keep cumulative volume constant, excitation wavelength 435nm, point
Its corresponding fluorescence intensity is not measured（See Fig. 3）.Test result indicates that with Cu2+The increase of concentration, fluorescence emission peak gradually subtract
It is weak, work as Cu2+Material amount for 1.0 times of amount of probe substance when, reaction is complete.In Fig. 4, the fitting chart of fluorescence titration
Bright probe WP and Cu2+Between coordination ratio be 1:1.
4th, probe WP is to Cu2+The measure of minimum detection limit
25 DEG C, using fluorescence titration spectrum and fitted figure, pass through test limit formula：CDL=3 σ/k, probe WP is can obtain to Cu2+
Minimum detection limit up to 4.3 × 10-3µM（0.043ppm）, and work as Cu2+Concentration when between 0.1 ~ 5.0 μM, probe WP
Detection Cu can be quantified2+。
Abundant experimental results show, in DMSO-HEPES (1:1 v/v) in system, probe WP can be realized to copper ion
Fluorescence identifying and quantitative analysis.
3rd, probe WP is in detection Cu2+Application in water sample
In order to study probe WP in detection Cu2+Applicability, we have chosen Yellow River water samples and laboratory running water water sample, warp
Filtering shows that Cu is not present in water2+.According in DMSO/HEPES（1:1v/v, pH=7.4）Optimal conditions in system,
Tested under 435nm excitation wavelengths.By water sample and 2.00, the standard Cu of 3.00,4.00 μM of various concentrations level2+
Solution blends, and is then tested and analyzed with probe WP, and experimental data is as shown in table 1.The Cu of all water samples2+ The rate of recovery and relative
Standard deviation achieves satisfactory results, and shows fluorescence probe WP Cu suitable for environmental water sample2+ Detection.
The present invention has advantages below compared with the prior art：
1st, in bromo- 1, the 8- naphthalimides synthesis of intermediate product N- normal-butyls -4-, the excessive uninanned platform of ethylenediamine is applied
Method, significantly improve yield and purity；
2nd, because target product is easily soluble in water, it is difficult to purify, using base exchange method, obtain pureN- normal-butyl -4- [second
Diamines -2-N,N'- two (3- propionic acid)] -1,8- naphthalimides.
3rd, the probe material is in DMSO/HEPES (v/v 1:1) in buffer system, selective enumeration method copper ion simultaneously occurs glimmering
Optical quenching, realization quantitatively detect copper ion, and detection sensitivity is high, and identification is not disturbed by other ions, therefore, can conduct
Fluorescence probe is applied to the detection of heavy metal ion, the detection of copper ion especially in biological tissue and environmental wastewater.
Brief description of the drawings
Fig. 1 is probe WP（5µM）And it adds 10 times of Na+, K+, Ca2+, Mg2+, Al3+, Pb2+, Fe3+,
Ni2+, Zn2+, Hg+, Ag+, Co2+, Cr2+, Mn2+, Cd2+And Cu2+When fluorescence spectrum（Excitation wavelength：435nm, transmitting
The nm of wavelength 532）.
Fig. 2 be in the presence of other cations probe WP to Cu2+The anti-interference figure of change in fluorescence.
Fig. 3 is the Cu of various concentrations2+In the presence of probe WP fluorescence titration spectrum.
Fig. 4 is the Cu of various concentrations2+In the presence of probe WP fluorescence titration fitted figure.
Embodiment
Below by preparation of the specific implementation to probe WP of the present invention and the fluorescence identifying methods and applications to copper ion
It is described in detail.
1st, probe WP preparation：
（1）NThe synthesis of the bromo- 1,8- naphthalimides of-normal-butyl -4-：Weigh 15g（0.054mol）The bromo- 1,8- naphthalene anhydrides of 4- and 7.9g
（0.108mol）N-butylamine, it is added in 500mL round-bottomed flasks, adding 300mL absolute ethyl alcohols makes it well mixed, and stirring rises
Warm to 80 DEG C, back flow reaction 3h；After the completion of reaction, gained light yellow mixture is cooled to room temperature, filtered, and use absolute ethyl alcohol
Washing 3 times, is put into oven drying 24h, obtainsNBromo- 1, the 8- naphthalimides of-normal-butyl -4-, 17.0g, yield 94.5%.mp:
107-109℃.Rf=0.75（CH2Cl2）. Elem.Anal.calcd. C 57.85; H 4.25; N 4.22 %; found:
C 57.79; H 4.28; N 4.19 %。
（2）NThe synthesis of-normal-butyl -4- ethylenediamine -1,8- naphthalimides：Weigh ethylenediamine 12.2g（201.67mmol）In
In 100mL three-necked flasks, by its heating water bath to 65 DEG C, addNThe bromo- 1,8- naphthalimides 1.0g of-normal-butyl -4-
（3.01mmol）, add several times, be stirred at reflux reaction 4h；After the completion of reaction, reaction gained light brown mixture is cooled to
Room temperature, 10mL distilled water is added in three-necked flask, three-necked flask is put into frozen water and stirs 30min, treats that a large amount of solids separate out
Shi Jinhang is filtered, and gained solid is repeatedly washed with distilled water, is then placed in oven drying 24h.It is dried thick to weigh 0.5g
Product adds 100mL toluene and recrystallized, obtain orange/yellow solid in 250mL round-bottomed flasksN- normal-butyl -4- second two
Amine -1,8- naphthalimide, 0.26g, yield 52%.mp: 129-132℃.Rf=0.78（CH2Cl2/CH3OH=5:1）.
Elem.Anal.calcd. C 69.43; H 6.80; N 13.49 %; found: C 69.38; H 6.89; N 13.41
%。
（3）N- normal-butyl -4- [ethylenediamine -2-N,N'- bis- (3- methyl propionates)] -1,8- naphthalimides synthesis：
In 250mL flasks, 2g is added（6.42mmol）N- normal-butyl -4- ethylenediamines -1,8- naphthalimide and 80mL methanol, treat that solid is complete
After portion's dissolving, then by 5.5g（63.89mmol）Methyl acrylate（70mL methanol）Flask is added dropwise, it is stirred at normal temperatures
Reaction 12 days, yellow mercury oxide separate out, and filtration washing, are put into oven drying 24h, 1.95g, yield 62.7%.mp: 39-43℃.
Rf=0.32（CH2Cl2）.Elem.Anal.calcd. C 64.58; H 6.88; N 8.69 %; found: C 64.51; H
6.99; N 8.45 %。
（4）N- normal-butyl -4- [ethylenediamine -2-N,N'- two (3- propionic acid)] -1,8- naphthalimides synthesis：N- normal-butyl-
4- [ethylenediamine -2-N,N'- bis- (3- methyl propionates)] -1,8- naphthalimides 3M potassium hydroxide-methanol alkaline hydrolysis, concentration, after
The cationic ion exchange column of acid activation, crude product is concentrated to give, water recrystallization, obtains pure target product probe WP, yield
60.9%。
mp: 217-219℃。MS (ES+) m/z = 456.2067 (M + H)+. FT-IR (v max, KBr, cm-1): 759 (ν Ar ); 3381 (νNH); 2603 and 2828 (νN); 2871 and 2960 (νCH);1684 (ν asN–C=O); 1646 (ν sN–C=O); 1717 (νC=O of COOH); 3663 and 3669 (νOH of COOH); 1550
and 1588 (νC=C, aromatic); 1300 and 1362 (νC–O of COOH).UV-vis. (in DMSO,
nm): 260, 444. 1H-NMR (300 MHz, DMSO-d 6 ): δ = 8.57 (d, 1H, J = 7.3 Hz,
naphthalimide H-5); 8.45 (d, 1H, J = 8.6 Hz, naphthalimide H-2); 8.38 (dd,
1H, J = 8.3 Hz, J = 1.0 Hz, naphthalimide H-7); 7.60(dd, 1H, J = 8.3 Hz, J =
7.3 Hz, naphthalimide H-6); 6.67 (d, 1H, J = 8.6 Hz, naphthalimide H-3); 6.28
(m, 1H, NH); 4.16 (t, 2H,J = 7.6 Hz, (CO)2NCH2 ); 11.34 (s, 2H, 2× OH); 3.44
(m, 2H,ArNHCH2 ); 2.83 (m, 6H, 3×NCH2); 2.34 (t, 4H, J = 6.4 Hz, 2×CH2 COOH);
1.57 (m, 2H, CH2 CH 2 CH2CH3); 1.32 (m, 2H,CH2CH2 CH2 CH3); 0.96 (t, 3H, J = 7.2 Hz,
CH2CH2CH2 CH 3 ). 13C-NMR (400 MHz, DMSO-d 6 ): 178.83 , 168.79, 167.96, 155.42,
139.19, 139.19, 135.63, 134.37, 133.29, 132.75–131.72, 129.38, 126.92,
125.17, 112.99, 108.94 , 56.16, 54.05, 45.83, 45.23, 45.02, 44.81, 44.60,
44.40, 44.19, 44.05, 37.11, 34.95, 25.00, 18.88。
WP synthesis type is as follows：
。
2nd, probe WP fluorescence identifyings copper ion
In 2mL DMSO/HEPES (v/v 1:1, pH=7.4) in buffer system, fixed probe WP is added dropwise（1×10-3Mol/L, 10
µL）, it is then respectively adding 100 μ L Na+, K+, Ca2+, Mg2+, Al3+, Pb2+, Fe3+, Ni2+, Zn2+, Cu2+, Hg2+, Ag+, Co2+,
Cr3+, Mn2+, Cd2+Metal ion（1×10-3mol/L）.Only Cu2+Addition cause probe WP DMSO/HEPES fluorescence subtract
It is weak and be quenched, and other metal ions add and WP fluorescence intensity are not responded significantly.
3rd, Cu in actual water sample2+ Measure
In 1mL DMSO and 1mL HEPES cushioning liquid (pH=7.4), probe WP storing solution is measured（1×10-3mol/L）
20 μ L, stir, and add 20 μ L water samples（Huanghe water or running water）With 20 μ L2.00 μM, 3.00 μM, 4.00 μM of difference
The standard Cu of concentration level2+ Solution, fluorescence intensity is measured under 435nm excitation wavelengths, then passes through fluorescence titration fit line
Determine Cu2+Concentration（Fig. 4）.
Copper ion concentration is between 0.1 ~ 5.0 μM, the fluorescence intensity and Cu of probe2+Concentration is in good linear relationship, line
Property fit equation is F=4324.7-31.5 [Cu2+] (degree of fitting R2 = 0.9912)。
Determine in water sample, Cu2+Concentration is 2.00,3.00,4.00 μM；Cu2+ The rate of recovery is 98 ~ 105.8%；Standard deviation
Difference is 0.03 ~ 0.32.
Claims (10)
1. a kind of water-soluble copper ion fluorescence probe material based on naphthalimide dicarboxylic acids, its structural formula are as follows：
。
A kind of 2. preparation side of the water-soluble copper ion fluorescence probe material based on naphthalimide dicarboxylic acids as claimed in claim 1
Method, comprise the following steps：
（1）The synthesis of the bromo- 1,8- naphthalimides of N- normal-butyls -4-：In ethanol, bromo- 1, the 8- naphthalene anhydrides of 4- flow back into n-butylamine
Row amidation process, cooling, solid is separated out, washed, dried, obtainNThe bromo- 1,8- naphthalimides of-normal-butyl -4-；
（2）NThe synthesis of-normal-butyl -4- ethylenediamine -1,8- naphthalimides：Under condition of no solvent,NThe bromo- 1,8- of-normal-butyl -4-
Naphthalimide carries out substitution reaction with ethylenediamine, is cooled down after the completion of reaction, adds elutriation to go out precipitation, obtains intermediate productN- positive fourth
Base -4- ethylenediamine -1,8- naphthalimides；
（3）N- normal-butyl -4- [ethylenediamine -2-N,N'- bis- (3- methyl propionates)] -1,8- naphthalimides synthesis：First willN- just
Butyl -4- ethylenediamines -1,8- naphthalimide dissolves in methyl alcohol, adds excessive methyl acrylate, reaction 11 ~ 13 is stirred at room temperature
My god, yellow mercury oxide separates out, and filters, and washing, obtainsN- normal-butyl -4- [ethylenediamine -2-N,N'- bis- (3- methyl propionates)] -1,8-
Naphthalimide；
（4）N- normal-butyl -4- [ethylenediamine -2-N,N'- two (3- propionic acid)] -1,8- naphthalimides synthesis：WillN- normal-butyl -4-
[ethylenediamine -2-N,N'- bis- (3- methyl propionates)] -1,8- naphthalimides carry out alkaline hydrolysis with potassium hydroxide-methanol solution, concentrate,
The cationic ion exchange column of acid activation is crossed, concentrates, obtains target productN- normal-butyl -4- [ethylenediamine -2-N,N'- two (3- third
Acid)] -1,8- naphthalimides --- water-soluble copper ion fluorescence probe material.
A kind of 3. preparation side of the water-soluble copper ion fluorescence probe material based on naphthalimide dicarboxylic acids as claimed in claim 2
Method, it is characterised in that：Step（1）In, the mol ratio of bromo- 1, the 8- naphthalene anhydrides of 4- and n-butylamine is 1:1~1:3.
A kind of 4. preparation side of the water-soluble copper ion fluorescence probe material based on naphthalimide dicarboxylic acids as claimed in claim 2
Method, it is characterised in that：Step（1）In, amidation process temperature is 75 ~ 85 DEG C, and the reaction time is 3 ~ 4 hours.
A kind of 5. preparation side of the water-soluble copper ion fluorescence probe material based on naphthalimide dicarboxylic acids as claimed in claim 2
Method, it is characterised in that：Step（2）In,NThe mol ratio of the bromo- 1,8- naphthalimides of-normal-butyl -4- and ethylenediamine is 1:60~1:
70。
A kind of 6. preparation side of the water-soluble copper ion fluorescence probe material based on naphthalimide dicarboxylic acids as claimed in claim 2
Method, it is characterised in that：Step（2）In, the temperature of substitution reaction is 60 ~ 70 DEG C, and the reaction time is 3 ~ 4 hours.
A kind of 7. preparation side of the water-soluble copper ion fluorescence probe material based on naphthalimide dicarboxylic acids as claimed in claim 2
Method, it is characterised in that：Step（3）In,N- normal-butyl -4- ethylenediamine -1,8- naphthalimides dissolve mole with methyl acrylate
Than for 1:9~1:11.
A kind of 8. preparation side of the water-soluble copper ion fluorescence probe material based on naphthalimide dicarboxylic acids as claimed in claim 1
Method, it is characterised in that：Step（4）In, the concentration of potassium hydroxide-methanol solution is 2 ~ 4 mol/Ls；Potassium hydroxide-methanol solution
The temperature for carrying out alkaline hydrolysis is 70 ~ 80 DEG C, and the time is 2 ~ 3 hours.
9. a kind of as claimed in claim 1 known based on the water-soluble copper ion fluorescence probe material of naphthalimide dicarboxylic acids in fluorescence
Application in other copper ion, it is characterised in that：In the DMSO/HEPES buffer systems of copper ion fluorescence probe material, drip respectively
Add Na+, K+, Ca2+, Mg2+, Al3+, Pb2+, Fe3+, Ni2+, Zn2+, Cu2+, Hg2+, Ag+, Co2+, Cr3+, Mn2+, Cd2+Solution, only
Cu2+Addition cause water-soluble copper ion fluorescence probe material DMSO/HEPES systems fluorescent weakening and be quenched, and
Other metal ions add not to be responded to the fluorescence intensity of water-soluble copper ion fluorescence probe material DMSO/HEPES systems.
10. a kind of water-soluble copper ion fluorescence probe material based on naphthalimide dicarboxylic acids as claimed in claim 1 is detecting
The application of Determined Copper in Aqueous Solution, it is characterised in that：Determined Copper in Aqueous Solution concentration between 0.1 ~ 5.0 μM, copper ion concentration with it is glimmering
Luminous intensity is in following linear relationship：
F = 4324.7-31.5[Cu2+]
F --- fluorescence intensity
C——Cu2+Concentration, unit：µM.
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Cited By (4)
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| WO2019196022A1 (en) * | 2018-04-10 | 2019-10-17 | 苏州大学张家港工业技术研究院 | 1,8-naphthalimide derivative, preparation method therefor and use thereof |
| CN112794819A (en) * | 2019-11-13 | 2021-05-14 | 湖南超亟化学科技有限公司 | Preparation method and application of novel fluorescent probe capable of being used for iron ion specificity detection based on molecular isomerization mechanism |
| CN113788789A (en) * | 2021-10-13 | 2021-12-14 | 哈尔滨理工大学 | Preparation method and application of fluorescent probe for continuously detecting copper ions and glyphosate |
| CN114213326A (en) * | 2022-01-21 | 2022-03-22 | 辽宁科技大学 | Naphthalimide fluorescent molecular probe for copper ion detection and preparation and use methods thereof |
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2017
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| RAMAN PARKESH，ET AL.: "Highly selective 4-amino-1,8-naphthalimide based fluorescent photoinduced electron transfer (PET) chemosensors for Zn(II) under physiological pH conditions", 《ORG. BIOMOL. CHEM.》 * |
| THORFINNUR GUNNLAUGSSON，ET AL.: "A highly selective and sensitive fluorescent PET (photoinduced electron transfer) chemosensor for Zn(II)", 《ORG. BIOMOL. CHEM.》 * |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019196022A1 (en) * | 2018-04-10 | 2019-10-17 | 苏州大学张家港工业技术研究院 | 1,8-naphthalimide derivative, preparation method therefor and use thereof |
| US11505530B2 (en) | 2018-04-10 | 2022-11-22 | Soochow University | 1,8-naphthalimide derivative, preparation method therefor and use thereof |
| CN112794819A (en) * | 2019-11-13 | 2021-05-14 | 湖南超亟化学科技有限公司 | Preparation method and application of novel fluorescent probe capable of being used for iron ion specificity detection based on molecular isomerization mechanism |
| CN112794819B (en) * | 2019-11-13 | 2023-10-10 | 湖南超亟检测技术有限责任公司 | Preparation method and application of fluorescent probe based on molecular isomerization mechanism and capable of being used for iron ion specificity detection |
| CN113788789A (en) * | 2021-10-13 | 2021-12-14 | 哈尔滨理工大学 | Preparation method and application of fluorescent probe for continuously detecting copper ions and glyphosate |
| CN114213326A (en) * | 2022-01-21 | 2022-03-22 | 辽宁科技大学 | Naphthalimide fluorescent molecular probe for copper ion detection and preparation and use methods thereof |
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