CN109761978A - A near-infrared fluorescent probe for detecting thiophenol and its synthesis method and application - Google Patents
A near-infrared fluorescent probe for detecting thiophenol and its synthesis method and application Download PDFInfo
- Publication number
- CN109761978A CN109761978A CN201910046884.7A CN201910046884A CN109761978A CN 109761978 A CN109761978 A CN 109761978A CN 201910046884 A CN201910046884 A CN 201910046884A CN 109761978 A CN109761978 A CN 109761978A
- Authority
- CN
- China
- Prior art keywords
- thiophenol
- probe
- molecular probe
- benzenethiol
- detection
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 title claims abstract description 168
- 239000007850 fluorescent dye Substances 0.000 title abstract description 6
- 238000001308 synthesis method Methods 0.000 title abstract 2
- 239000000523 sample Substances 0.000 claims abstract description 27
- 238000001514 detection method Methods 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002689 soil Substances 0.000 claims abstract description 5
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003068 molecular probe Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 229940125782 compound 2 Drugs 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 2
- KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 239000007853 buffer solution Substances 0.000 claims description 2
- 238000004737 colorimetric analysis Methods 0.000 claims description 2
- 238000001917 fluorescence detection Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- 239000011259 mixed solution Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- -1 2,4-dinitrophenoxy Chemical group 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 238000004458 analytical method Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 238000007689 inspection Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 108010024636 Glutathione Proteins 0.000 description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
- 235000018417 cysteine Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000007421 fluorometric assay Methods 0.000 description 2
- 229960003180 glutathione Drugs 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000001738 Nervous System Trauma Diseases 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- JYISZVSPRRFQBR-UHFFFAOYSA-N benzene;benzenethiol Chemical compound C1=CC=CC=C1.SC1=CC=CC=C1 JYISZVSPRRFQBR-UHFFFAOYSA-N 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000002795 fluorescence method Methods 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000036473 myasthenia Effects 0.000 description 1
- 208000028412 nervous system injury Diseases 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
本发明公开了一种高选择性检测苯硫酚的近红外荧光探针及其合成方法和应用，属于化学分析检测技术领域。本发明探针由二氰基异佛尔酮‑久洛尼定大π体系与2,4‑二硝基氟苯反应得到，具有如下结构：此探针的荧光团为二氰基异佛尔酮‑久洛尼定大π体系，对苯硫酚的响应基团为2,4‑二硝基苯氧基。该探针分子对苯硫酚有高的选择性和灵敏度，检测范围为1–60μmol·L‑1，检测限为0.13μmol·L‑1。该探针可用于水体、土壤以及细胞内苯硫酚的检测。
The invention discloses a near-infrared fluorescent probe for highly selective detection of thiophenol, a synthesis method and application thereof, and belongs to the technical field of chemical analysis and detection. The probe of the present invention is obtained by reacting a dicyanoisophorone-julonidine large π system with 2,4-dinitrofluorobenzene, and has the following structure: The fluorophore of this probe is a dicyanoisophorone-julonidine large π system, and the responsive group to thiophenol is 2,4-dinitrophenoxy. The probe molecule has high selectivity and sensitivity to thiophenol, the detection range is 1–60 μmol·L ‑1 , and the detection limit is 0.13 μmol·L ‑1 . The probe can be used for the detection of thiophenol in water, soil and cells.
Description
Technical field
The invention belongs to chemical analysis detection technique fields, and in particular to a kind of highly selective inspection of near-infrared trun-on type
It surveys the fluorescence probe of benzenethiol and its closes method and the application in terms of detecting benzenethiol.
Background technique
Benzenethiol (C6H5SH, PhSH) it is a kind of aromatic yl sulfide with high reaction activity, have in compound probability wide
General application, such as sulfa drugs, pesticide and high molecular synthesis.Benzenethiol has very high toxicity, breathing but then
And the intake of skin will lead to various illnesss, such as expiratory dyspnea, myasthenia, central nervous system injury are even dead.U.S.'s occupation peace
Full health office defines that the working environment maximum concentration of benzenethiol is 0.1ppm.With benzenethiol a large amount of industrial applications discharge and
Toxic action, developing highly sensitive, high selection detection benzenethiol method is very important to environment measuring and protection.
Based on molecular probe fluorescence method inspection method have sample treatment it is succinct, it is low in cost and it is easy to operate quickly etc. it is excellent
Point, is developed in recent years and utilizes.But the fluorescent probe molecule for detecting benzenethiol developed at present largely emits
Small (the Zhang W.J.Dyes and Pigments of stokes displacement value of the wavelength not in near-infrared region or probe
2016,133,248；Pagidi S.Langmuir 2018,34,8170；Genga Y.Sensors&Actuators:
B.Chemical 2018,273,1670.), since the light compared with short-wave band is weak to biological penetration capacity and there are biological damage,
And small stokes displacement value can bring the interference of exciting light, therefore, it is dry that this kind of probe molecule is unfavorable for complex sample background
The elimination disturbed, to be unfavorable for the detection of complex environment sample and biological sample.And it is close with larger stokes displacement value
Infrared fluorescence probes can overcome the above problem well.
Summary of the invention
For above situation, it is an object of the present invention to provide it is a kind of it is easily prepared, performance is stable, has larger Stokes position
The novel near-infrared fluorescent molecular probe of shifting value, and the synthetic method of the probe is provided, also go out in this foundational development to benzenethiol
Carry out highly selective and highly sensitive detection method.
Purpose to realize the present invention, the present invention have stronger necleophilic reaction characteristic using benzenethiol, can be with electron deficient point
Son or group react, and reacting for specificity can occur with benzenethiol for 2,4- dinitrodiphenyl ethers, and this patent uses 2,4- bis-
Nitro phenylate is the response group of benzenethiol.On the other hand, the big π system of dicyano isophorone-julolidine has good
Long wavelength's fluorescent emission performance, and the push-and-pull of former fluorescent molecule can be changed by introducing different electron-withdrawing groups in phenolic hydroxyl group position
For the characteristic of electron system to change its photoluminescent property, this patent designs big pi-conjugated sliding body pastern bone frame as illuminophore, synthesis
For detecting the fluorescent molecular probe of benzenethiol.
The fluorescent molecular probe of the detection benzenethiol, structural formula are as follows:
Its synthetic reaction process is as follows:
Its synthetic method is specific as follows:
In organic solvent, alkali compounds is added, compound 2 is reacted with 2,4-dinitrofluorobenzene, after isolating and purifying
To final goal products probe molecule 1.
The organic solvent is selected from one of acetonitrile, tetrahydrofuran, dimethylformamide, N-Methyl pyrrolidone.
The alkali compounds be selected from potassium carbonate, sodium carbonate, sodium acetate, triethylamine, N, N- diisopropylcarbodiimide its
One of.
Reaction time is 2-24h.
Reaction temperature is 50-120 DEG C.
Reaction condition is still more preferably as follows:
It reacts organic solvent and is selected from acetonitrile.
Reaction base is selected from potassium carbonate.
Reaction time is 8h.
Reaction temperature is 80 DEG C.
Qualitative and quantitative determination is carried out to benzenethiol using the molecular probe, for benzene in water body, soil or biosystem
The detection of thiophenol.
When using colorimetric method or Fluorometric assay, molecular probe is dissolved in the mixing buffer solution of water and dimethyl sulfoxide
In, benzenethiol is tested.After benzenethiol is added, benzenethiol energy nucleophilic attack phenoxy group, and it is further anti-by removing
It answers, makes the phenolic hydroxyl group separate out of fluorogen, to generate strong Intramolecular electron transfer (ICT) effect, make probe solution
Absorption spectrum red shift occurs, and supervene strong near-infrared fluorescent emission characteristics.
When using Fluorometric assay, the fluorescent molecular probe is 1-60 μm of olL to the detectable concentration of benzenethiol-1, inspection
Survey is limited to 0.13 μm of olL-1。
Fluorescent probe molecule of the present invention have the advantages that following features and:
The fluorescent probe molecule is with good stability and optical property, before reacting maximum absorption wave it is a length of~550nm,
Independent solution takes on a red color, unstressed configuration transmitting；With the addition of benzenethiol, probe molecule in ultraviolet absorption peak red shift to~685nm,
Solution is blue, has strong fluorescent emission property at~730nm.
Probe molecule raw material of the present invention is easy to get, and synthetic yield is higher, and up to 86% or more, stable optical performance (is visited
Needle mother liquor can be stable storage indoors three months or more, and spectral property remains unchanged), it is highly selective and highly sensitive, to benzene
Thiophenol recognition capability is strong, and response speed is very fast, and response range is 1-60 μm of olL-1, low (the 0.13 μm of olL of detection limit-1), because
This, the type probe can be used for water body, in soil and biosystem benzenethiol detection.
Detailed description of the invention
Fig. 1 is the nuclear magnetic resonance spectroscopy for the molecular probe that the present invention synthesizes；
Fig. 2 is the uv atlas A and fluorescence spectra B that molecular probe of the present invention reacts front and back with benzenethiol, wherein A figure
In, before 1- reaction, after 2- reaction；In B figure, before 1- reaction, after 2- reaction；
Fig. 3 is 10 μm of olL of the present invention-1Molecular probe fluorescence emission spectrogram of compound after various concentration benzenethiol is added, from a
To w, benzenethiol concentration is respectively 0,1,2,5,10,15,20,25,30,35,40,45,50,55,60,70,80,90,100,
120、150、180、100μmol·L-1, solution system is the phosphate buffer solution (H of water and dimethyl sulfoxide2O/DMSO=1/1,
V/v, 10mM, pH 7.4), abscissa is wavelength, and ordinate is fluorescence intensity.
Fig. 4 is the concentration standard curve figure of benzenethiol, i.e. 10 μm of olL-1Molecular probe of the present invention, reaction front and back exist
The linear relationship with benzenethiol concentration of fluorescent emission intensity at 730nm；Abscissa is the concentration of benzenethiol, and ordinate is fluorescence
Intensity.
Fig. 5 is molecular probe of the present invention to benzenethiol selectivity；That is 200 μm of ol are added in 10 μM of molecular probes of the present invention
L-1Different material (cysteine, glutathione, homocysteine, S2-, phenol, aniline, AcO-、ClO-、CO3 2-、F-、I-、N3 -、
NO3 -、SO3 2-) after, the variation of fluorescent emission intensity at 730nm；Abscissa is the interfering substance of test, and ordinate is that fluorescence is strong
Degree.
Fig. 6 is the imaging picture that molecular probe of the present invention detects the intracellular benzenethiol of Hela.(A, B) is the present invention point respectively
Sub- fluorescence probe (10 μm of olL-1) culture Hela light field picture and fluorescence picture；(C, D) is that molecule of the present invention is glimmering respectively
Light probe (10 μm of olL-1) and benzenethiol (50 μm of olL-1) culture Hela cell light field picture and fluorescence picture.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
Embodiment 1: the synthesis of fluorescent molecular probe
By compound 2 (0.385g, 1mmol), K is added in 2,4-dinitrofluorobenzene (0.186g, 1mmol)2CO3(0.685g,
5mmol), 80 DEG C of reaction 8h in solvent acetonitrile (20mL).To which after reaction, vacuum distillation removes solvent, column chromatography post separation
(eluant, eluent is methylene chloride) obtains product reddish black solid 0.473g (yield: 86%).Product structure formula is as follows:
1H NMR(400Hz,CDCl3): δ 8.70 (d, J=8.1Hz, 1H), 8.05 (d, J=8.7Hz, 1H), 7.98 (d, J
=7.8Hz, 1H), 7.68 (ddd, J=32.6,20.0,11.5Hz, 5H), 7.50 (d, J=8.5Hz, 2H), 7.23 (d, J=
16.2Hz, 1H), 6.64 (d, J=8.4Hz, 2H), 2.86 (s, 6H) .MS [ESI]: m/z, calcd for [M+H]+552.22；
found522.14。
Embodiment 2: fluorescence detection of the probe to benzenethiol
Above-mentioned obtained molecular probe is dissolved in the phosphate buffer solution (H of water and dimethyl sulfoxide2O/DMSO=1/1, v/
V, 10mM, pH 7.4), it is configured to 10 μm of olL-1Probe solution.10 μ that 2mL is prepared are added in the cuvette of 3mL
mol·L-1Probe solution of the present invention, the benzenethiol for being then respectively adding various concentration uniformly mixes, test its fluorescence spectrum,
As a result as shown in Figure 3.With solution, fluorescent emission intensity maps to the concentration of benzenethiol at 730nm, and benzenethiol concentration is in 1-60 μ
mol·L-1When in range, good linear relationship (Fig. 4) is presented between the two, is able to achieve determining for benzenethiol in the concentration range
Amount detection, and solution becomes blue from red, is also applied for open hole detection.And this probe is not by some other Common materials
Influence, such as cysteine, glutathione, homocysteine, S2-, phenol, aniline, AcO-、ClO-、CO3 2-、F-、I-、N3 -、
NO3 -、SO3 2-.Under the conditions of existing for the above-mentioned chaff interferent, probe containing benzenethiol to still having good selectivity and sensitivity (figure
5)。
By cell with containing after probe culture solution culture of the present invention, benzenethiol is added, and is cultivated in the solution containing benzenethiol.
Cell fluorescence imaging can observe red fluorescence (Fig. 6).
As can be seen that the present invention is able to achieve the qualitative and quantitative analysis to benzenethiol, high sensitivity, detection is limited up to 0.13 μ
mol·L-1, and it is anti-interference strong, and it is able to achieve the detection of intracellular benzenethiol.
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910046884.7A CN109761978A (en) | 2019-01-18 | 2019-01-18 | A near-infrared fluorescent probe for detecting thiophenol and its synthesis method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910046884.7A CN109761978A (en) | 2019-01-18 | 2019-01-18 | A near-infrared fluorescent probe for detecting thiophenol and its synthesis method and application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109761978A true CN109761978A (en) | 2019-05-17 |
Family
ID=66452475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910046884.7A Pending CN109761978A (en) | 2019-01-18 | 2019-01-18 | A near-infrared fluorescent probe for detecting thiophenol and its synthesis method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109761978A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110092773A (en) * | 2019-05-24 | 2019-08-06 | 赣南师范大学 | A kind of oxa anthracenes derivative and its preparation method and application |
| CN110511742A (en) * | 2019-09-04 | 2019-11-29 | 中南大学 | A near-infrared fluorescent probe for specific recognition of polyhydrogen sulfide |
| CN110615786A (en) * | 2019-07-17 | 2019-12-27 | 浙江工业大学 | Near-infrared fluorescent compound for detecting viscosity and preparation and application thereof |
| CN110642857A (en) * | 2019-09-20 | 2020-01-03 | 台州学院 | A bifunctional fluorescent probe for detecting viscosity and pH and its preparation and application |
| CN111138431A (en) * | 2020-01-13 | 2020-05-12 | 商丘师范学院 | A kind of reactive fluorescent probe for detecting thiophenol and its synthesis method and application |
| CN111205243A (en) * | 2020-02-27 | 2020-05-29 | 山西大学 | Reagent for distinguishing and detecting thiophenol and synthetic method and application thereof |
| CN112679386A (en) * | 2021-01-26 | 2021-04-20 | 吕梁学院 | Fluorescent probe for detecting 4-methylthiophenol and preparation method thereof |
| CN115819343A (en) * | 2022-11-23 | 2023-03-21 | 上海工程技术大学 | Open type fluorescent probe material, preparation method thereof and method for detecting thiophenol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108129487A (en) * | 2016-12-01 | 2018-06-08 | 齐鲁工业大学 | A kind of benzenethiol fluorescence probe of Coumarins and preparation method thereof |
| CN108191881A (en) * | 2018-01-18 | 2018-06-22 | 中南大学 | A kind of fluorescence probe for identifying benzenethiol |
-
2019
- 2019-01-18 CN CN201910046884.7A patent/CN109761978A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108129487A (en) * | 2016-12-01 | 2018-06-08 | 齐鲁工业大学 | A kind of benzenethiol fluorescence probe of Coumarins and preparation method thereof |
| CN108191881A (en) * | 2018-01-18 | 2018-06-22 | 中南大学 | A kind of fluorescence probe for identifying benzenethiol |
Non-Patent Citations (5)
| Title |
|---|
| KAI WANG ET AL: ""Dual quenching strategy for sensitive detection of toxic thiolphenols based on a NIR-illuminant platform with a large Stokes shift"", 《DYES AND PIGMENTS》 * |
| M.M. SEVRYUKOVA ET AL.: ""Dynamics of transfer of electron excitation in a donor-acceptor system with a carbon chain and ways of its relaxation"", 《SEMICONDUCTOR PHYSICS, QUANTUM ELECTRONICS & OPTOELECTRONICS》 * |
| YU CHENG ET AL.: ""A novel isophorone-based red-emitting/NIR probe for thiophenol and its application in real water sample and vivo"", 《SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY》 * |
| 宋晓睿等: ""以芳胺为电子给体的D-π-A有机光敏染料-染料敏化太阳电池中的应用"", 《化学进展》 * |
| 王春梅等主编: "《激光扫描共聚焦显微镜技术》", 31 July 2004, 西安：第四军医大学出版社 * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110092773A (en) * | 2019-05-24 | 2019-08-06 | 赣南师范大学 | A kind of oxa anthracenes derivative and its preparation method and application |
| CN110615786A (en) * | 2019-07-17 | 2019-12-27 | 浙江工业大学 | Near-infrared fluorescent compound for detecting viscosity and preparation and application thereof |
| CN110511742A (en) * | 2019-09-04 | 2019-11-29 | 中南大学 | A near-infrared fluorescent probe for specific recognition of polyhydrogen sulfide |
| CN110642857A (en) * | 2019-09-20 | 2020-01-03 | 台州学院 | A bifunctional fluorescent probe for detecting viscosity and pH and its preparation and application |
| CN110642857B (en) * | 2019-09-20 | 2020-12-01 | 台州学院 | A bifunctional fluorescent probe for detecting viscosity and pH and its preparation and application |
| CN111138431A (en) * | 2020-01-13 | 2020-05-12 | 商丘师范学院 | A kind of reactive fluorescent probe for detecting thiophenol and its synthesis method and application |
| CN111138431B (en) * | 2020-01-13 | 2022-02-15 | 商丘师范学院 | A kind of reactive fluorescent probe for detecting thiophenol and its synthesis method and application |
| CN111205243A (en) * | 2020-02-27 | 2020-05-29 | 山西大学 | Reagent for distinguishing and detecting thiophenol and synthetic method and application thereof |
| CN111205243B (en) * | 2020-02-27 | 2022-05-20 | 山西大学 | A kind of reagent for distinguishing and detecting thiophenol and its synthesis method and application |
| CN112679386A (en) * | 2021-01-26 | 2021-04-20 | 吕梁学院 | Fluorescent probe for detecting 4-methylthiophenol and preparation method thereof |
| CN112679386B (en) * | 2021-01-26 | 2021-12-10 | 吕梁学院 | A kind of fluorescent probe for detecting 4-methylthiophenol and preparation method thereof |
| CN115819343A (en) * | 2022-11-23 | 2023-03-21 | 上海工程技术大学 | Open type fluorescent probe material, preparation method thereof and method for detecting thiophenol |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109761978A (en) | A near-infrared fluorescent probe for detecting thiophenol and its synthesis method and application | |
| CN109761853A (en) | A near-infrared fluorescent probe for detecting thiophenol and its synthesis method and application | |
| Jiang et al. | An ultra-sensitive and ratiometric fluorescent probe based on the DTBET process for Hg 2+ detection and imaging applications | |
| Chen et al. | A new off–on chemosensor for Al 3+ and Cu 2+ in two different systems based on a rhodamine B derivative | |
| Niu et al. | A novel colorimetric and ratiometric fluorescent probe for sensing SO 2 derivatives and their bio-imaging in living cells | |
| Wu et al. | A selective cascade reaction-based probe for colorimetric and ratiometric fluorescence detection of benzoyl peroxide in food and living cells | |
| Paul et al. | Detection of hydrogen sulfide using BODIPY based colorimetric and fluorescent on-off chemosensor | |
| CN114516836A (en) | Fluorescent probe material, preparation method thereof and method for detecting sulfide | |
| CN106518763B (en) | Fluorescent probe for selective ratiometric detection of cyanide ions, synthesis method and application thereof | |
| Feng et al. | 1, 6-Elimination reaction induced detection of fluoride ions in vitro and in vivo based on a NIR fluorescent probe | |
| Ye et al. | 5G smartphone-adaptable fluorescence sensing platform for simultaneous detection of toxic formaldehyde and phosgene in different emission channels | |
| Yue et al. | A dual-response NIR fluorescent probe for separately and continuously recognizing H 2 S and Cys with different fluorescence signals and its applications | |
| CN109503515A (en) | A kind of methylene blue derivatives object and its synthetic method and application | |
| Shen et al. | A phenothiazine-based ratiometric fluorescent probe for detecting hypochlorite (ClO−) and its application in foods and water samples | |
| Zhao et al. | An ESIPT+ AIE based dual-response fluorescent probe for continuous detection of PhSH and HClO and visualization of PhSH-induced oxidative stress in living cells | |
| CN111138431B (en) | A kind of reactive fluorescent probe for detecting thiophenol and its synthesis method and application | |
| Yin et al. | A benzophenoxazine-based NIR fluorescent probe for the detection of hydrogen sulfide and imaging in living cells | |
| CN114249760A (en) | Synthesis and application of fluorescent probe capable of simultaneously distinguishing hypochlorous acid and hydrogen peroxide in three channels | |
| Zhang et al. | Pyrazole probes for the detection of N2H4 with ICT properties in live cells and soils | |
| Huang et al. | A novel anthracene-based receptor: highly sensitive fluorescent and colorimetric receptor for fluoride | |
| CN108863961B (en) | Triazole anthraquinone derivative silver ion fluorescent probe and preparation method and application thereof | |
| Du et al. | A phenothiazine-based ratiometric fluorescence probe for the detection of hydroxylamine in real water and living cells | |
| CN109734710A (en) | A kind of fluorescent probe for detecting cysteine and its synthesis method and application | |
| CN106397319A (en) | Fluorescent probe for proportionally detecting hydrazine, method for synthesizing fluorescent probe and application thereof | |
| CN115894293A (en) | A ratio-type near-infrared fluorescent probe for detecting hydrazine and its synthesis method and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190517 |