CN110016009B - Hypochlorous acid fluorescent probe and preparation method thereof - Google Patents

Hypochlorous acid fluorescent probe and preparation method thereof Download PDF

Info

Publication number
CN110016009B
CN110016009B CN201910403158.6A CN201910403158A CN110016009B CN 110016009 B CN110016009 B CN 110016009B CN 201910403158 A CN201910403158 A CN 201910403158A CN 110016009 B CN110016009 B CN 110016009B
Authority
CN
China
Prior art keywords
hypochlorous acid
fluorescent probe
acid fluorescent
preparation
reaction
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.)
Active
Application number
CN201910403158.6A
Other languages
Chinese (zh)
Other versions
CN110016009A (en
Inventor
段琴雅
张华堂
郑观生
李泽君
蒋银
何军
成晓玲
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Guangdong University of Technology
Original Assignee
Guangdong University of Technology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Guangdong University of Technology filed Critical Guangdong University of Technology
Priority to CN201910403158.6A priority Critical patent/CN110016009B/en
Publication of CN110016009A publication Critical patent/CN110016009A/en
Application granted granted Critical
Publication of CN110016009B publication Critical patent/CN110016009B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/04—Five-membered rings
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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"
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Analytical Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Optics & Photonics (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)

Abstract

The invention relates to the technical field of fluorescent probes, in particular to a hypochlorous acid fluorescent probe and a preparation method thereof. The invention provides a hypochlorous acid fluorescent probe with a molecular formula of C20H19NO2S, the structural formula is shown as formula I. The invention also provides a preparation method of the hypochlorous acid fluorescent probe, and the hypochlorous acid fluorescent probe is obtained through coupling reaction, substitution reaction and addition reaction respectively. The hypochlorous acid fluorescent probe and the preparation method thereof provided by the invention solve the technical problems of low sensitivity, poor selectivity and limited imaging application of the existing fluorescent probe.

Description

Hypochlorous acid fluorescent probe and preparation method thereof
Technical Field
The invention relates to the technical field of fluorescent probes, in particular to a hypochlorous acid fluorescent probe and a preparation method thereof.
Background
Hypochlorous acid is Cl-And H2O2An important activity is produced by the action of myeloperoxidase (myeloperoxidase) in biological systemsAnd (4) sexual oxygen. Although hypochlorous acid is present in very low concentrations in biological systems, it plays a key role in immune defense. However, due to its high reactivity, excessive hypochlorous acid can cause a series of diseases closely related to inflammation. Therefore, it is of great importance to establish a satisfactory detection method for detecting natural hypochlorous acid in living cells and living bodies.
Small molecule fluorescent probes have outstanding sensitivity and high temporal and spatial resolution in biological imaging applications compared to other conventional methods. In recent years, hypochlorous acid fluorescent probes based on different recognition receptors have been designed. However, despite their unique advantages in many respects, these fluorescent probes still suffer from low sensitivity, poor selectivity, and limited in vivo biological imaging applications.
Disclosure of Invention
The invention provides a hypochlorous acid fluorescent probe and a preparation method thereof, and solves the technical problems of low sensitivity, poor selectivity and limited imaging application of the conventional fluorescent probe.
The invention provides a hypochlorous acid fluorescent probe with a molecular formula of C20H19NO2S, the structural formula is shown as formula I,
Figure BDA0002060408650000011
the invention also provides a preparation method of the hypochlorous acid fluorescent probe, which comprises the following steps:
step 1: the 4- (methylamino) phenol sulfate, the tert-butyldimethylsilyl chloride and the imidazole are subjected to substitution reaction to obtain
Figure BDA0002060408650000012
Step 2: will be provided with
Figure BDA0002060408650000021
Obtained by a coupling reaction
Figure BDA0002060408650000022
And step 3: will be provided with
Figure BDA0002060408650000023
And tetrabutylammonium fluoride by substitution reaction
Figure BDA0002060408650000024
And 4, step 4:
Figure BDA0002060408650000025
dimercaptoethanol, trimethylsilyl trifluoromethanesulfonate and
Figure BDA0002060408650000026
obtained by addition reaction
Figure BDA0002060408650000027
Preferably, the molar ratio of 4- (methylamino) phenol sulfate, tert-butyldimethylsilyl chloride and imidazole in step 1 is 1:1.2: 4.
Preferably, the step 2 further comprises adding cesium carbonate, palladium acetate and 1,1 '-binaphthyl-2, 2' -bis-diphenylphosphine;
in step 2
Figure BDA0002060408650000028
The molar ratio of the cesium carbonate, the palladium acetate and the 1,1 '-binaphthyl-2, 2' -bis-diphenylphosphine is 1:2:4:0.05: 0.06.
Preferably, in step 3
Figure BDA0002060408650000031
And tetrabutylammonium fluoride in a molar ratio of 1: 3.
Preferably, in step 4
Figure BDA0002060408650000032
The molar ratio of dimercaptoethanol to trimethylsilyl trifluoromethanesulfonate was 1:2: 0.1.
Compared with the existing fluorescent probe, the hypochlorous acid fluorescent probe synthesized by the invention has the following advantages: (1) the synthesis is simple and convenient, the yield is high, the preparation is easy, and the method is suitable for large-scale synthesis and practical production application; (2) the detection method is simple and can be realized only by means of a fluorescence spectrometer. (ii) a (3) The hypochlorous acid probe has the advantages of good selectivity, high sensitivity and the like in response; (4) has the advantages of quick response and obvious phenomenon, and has wide application prospect.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below.
FIG. 1 is a nuclear magnetic hydrogen spectrum of a hypochlorous acid probe prepared in an example of the present invention;
FIG. 2 is a nuclear magnetic carbon spectrum of a hypochlorous acid probe prepared in an example of the present invention;
FIG. 3 is a graph showing the UV absorption before and after hypochlorous acid is added to a hypochlorous acid probe prepared in an example of the present invention;
FIG. 4 is a fluorescence spectrum of a hypochlorous acid probe prepared in an example of the present invention before and after hypochlorous acid is added.
FIG. 5 is a graph showing the results of analyzing the fluorescence intensity of hypochlorous acid probe prepared in the example of the present invention when other active molecules are added thereto.
Detailed Description
The invention provides a hypochlorous acid fluorescent probe and a preparation method thereof, and solves the technical problems of low sensitivity, poor selectivity and limited imaging application of the conventional fluorescent probe.
In order to make the objects, features and advantages of the present invention more obvious and understandable, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention, and it is obvious that the embodiments described below are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Step 1: 2.07g (6mmol) of 4- (methylamino) phenolsulfate, 1.09g (7.2mmol) of tert-butyldimethylsilyl chloride and 1.6g (24mmol) of imidazole were each introduced into a 50ml round-bottomed flask, and 20ml of methylene chloride was added as a solvent, stirred at room temperature and monitored by TLC. After the reaction was completed, the reaction solution was washed three times with saturated brine, dried over anhydrous sodium sulfate for 1 hour, suction-filtered and the solvent was removed under reduced pressure to obtain a crude product, which was then purified by silica gel column chromatography (eluent ethyl acetate: petroleum ether: 1: 40) to obtain 4- ((tert-butyldimethylsilyl) oxy) -N-methylaniline, i.e., compound 4, 1.28g, with a yield of 90%.
The reaction equation in step 1 is:
Figure BDA0002060408650000041
step 2: 950mg (4mmol) of the compound 4, 6-bromo-2-naphthaldehyde 470mg (2mmol), 1,1 '-binaphthyl-2, 2' -bis-diphenylphosphine 75mg (0.12mmol), palladium acetate 22.4mg (0.1mmol) and cesium carbonate 2.6g (8mmol) were added to a two-necked flask equipped with a reflux apparatus, deoxygenated, and a dry toluene solution was introduced as a solvent under argon conditions, refluxed for 3 hours, monitored by TLC. After completion of the reaction, a part of the solvent was removed under reduced pressure, the mixture was dissolved with dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, suction-filtered and the solvent was removed under reduced pressure to give a crude product, which was purified by silica gel column chromatography (eluent ethyl acetate: petroleum ether ═ 1:20) to give 6- ((4- ((tert-butyldimethylsilyl) oxy) phenyl) (methyl) amino) -2-naphthaldehyde, which was compound 3, 728mg, in 93% yield.
The reaction equation of step 2 is:
Figure BDA0002060408650000042
and step 3: 391mg (1mmol) of Compound 3 was charged into a 25ml round-bottom flask, 10ml of tetrahydrofuran solution was added as a solvent, 3ml (3mmol) of TBAF (tetrabutylammonium fluoride) was added, stirred at room temperature for 30min, monitored by TLC, the reaction solution was freed of the solvent by reduced pressure, dissolved in dichloromethane, washed with saturated brine, dried over anhydrous sodium sulfate, suction-filtered and freed of the solvent by reduced pressure to give a crude product, which was then purified by silica gel column chromatography (eluent: ethyl acetate: petroleum ether: 1:10) to give 6- ((4-hydroxyphenyl) (methyl) amino) -2-naphthaldehyde, i.e., Compound 2, 213mg, in 59% yield.
The reaction equation of step 3 is:
Figure BDA0002060408650000051
and 4, step 4: 139mg (0.5mmol) of Compound 2 are placed in a 10ml round-bottom flask, 8ml of dichloromethane solution are added as solvent, 69ul (1mmol) of dimercaptoethanol and 9ul (0.05mmol) of trimethylsilyl trifluoromethanesulfonate are added under argon, stirred at room temperature for 1h and monitored by TLC. After completion of the reaction, the reaction solution was washed with brine, dried over anhydrous sodium sulfate, filtered under suction and the solvent was removed under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography (eluent: ethyl acetate: petroleum ether: 1:10) to obtain 4- (((6- (1, 3-oxacyclopent-2-yl) cycloalkane-2-yl) (methyl) amino) phenol, i.e., hypochlorous acid fluorescent probe molecule 1.
The reaction equation of step 4 is:
Figure BDA0002060408650000052
FIG. 1 and FIG. 2 are respectively a hypochlorous acid fluorescent probe prepared in the example of the present invention1H NMR chart and13c NMR chart;
1H NMR(400MHz，CDCl3):δ7.73(s，1H),7.66(d，1H，J＝8.56Hz)，7.58(d,1H,J＝8.99Hz),7.50(d,1H,J＝6.84Hz),7.08(d,2H,J＝8.79Hz),7.04(s,1H),7.02(dd,1H,J＝2.43,8.96Hz),6.84(d,1H,J＝8.80Hz),6.17(s，1H),4.77(S,1H),4.57(m，1H),4.00(m，1H),3.34(S，1H),3.31(m，1H),3.22(m，1H)。
13C NMR(400MHz，CDCl3)：δ152.84,171.91,142.03，135.03,132.76，128.53,127.05，127.00，126.94,125.75，124.93，119.27，116.,41，108.72，88.70，71.97，40.91，34.16。
as described above, 3. mu.l of stock solution (1mM) of fluorescent probe molecule was added to 3ml of PBS buffer solution (0.01M, pH7.4), and then 3. mu.l of stock solution (100mM) of ClO-was added dropwise to record the change in fluorescence intensity, as can be seen from FIG. 3, the fluorescent probe molecule had a strong absorption peak at 311nm, and ClO was added-After. The absorption peak at 311nm disappeared and a new absorption peak appeared at 378 nm. Indicating that the probe molecule can react with hypochlorite ions.
To examine the change of fluorescence intensity of hypochlorous acid fluorescent probe molecules under different hypochlorous acid concentration conditions, 3ul of fluorescent probe stock solution (1mM) was added to 3ml of PBS buffer solution (0.01M, pH7.4), and then 3ul of ClO with different concentrations were added to each sample-(10,20,30,40,50,60,70,80,90,100mM), the change in fluorescence intensity was examined, and it can be seen from FIG. 4 that the change with ClO-The fluorescence intensity at 518nm gradually increased with increasing concentration. When the final concentration of the added hypochlorous acid is 100 mu M, the multiple of growth of the hypochlorous acid fluorescent probe molecule can reach 1100 times.
To test the selectivity of hypochlorous acid fluorescent probe molecules to other active molecules and hypochlorous acid, 3. mu.l of fluorescent probe stock solution (1mM) was added to 3ml of PBS buffer solution (0.01M, pH7.4), and then 3. mu.l of hypochlorous acid (10mM) and various common bioactive small molecules (50mM) such as cysteine, homocysteine, glutathione, ferrous ion, potassium ion, sulfite ion, nitrite ion, t-butanol hydroperoxide, hydroxyl radical, superoxide anion, nitrous peroxide ion were added, and the change in fluorescence after reaction with the probe was measured, respectively. As is clear from FIG. 5, only when hypochlorous acid was added, the fluorescence intensity of the hypochlorous acid fluorescent probe molecules was significantly changed. The probe has good selectivity.
The above-mentioned embodiments are only used for illustrating the technical solutions of the present invention, and not for limiting the same; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.

Claims (6)

1. The hypochlorous acid fluorescent probe is characterized in that the molecular formula is C20H19NO2S, the structural formula is shown as formula I,
Figure 147035DEST_PATH_IMAGE001
I。
2. the preparation method of the hypochlorous acid fluorescent probe is characterized by comprising the following steps of:
step 1: the 4- (methylamino) phenol sulfate, the tert-butyldimethylsilyl chloride and the imidazole are subjected to substitution reaction to obtain
Figure 544518DEST_PATH_IMAGE002
；
Step 2: will be provided with
Figure 273440DEST_PATH_IMAGE002
And
Figure 352254DEST_PATH_IMAGE003
obtained by a coupling reaction
Figure 850232DEST_PATH_IMAGE004
；
And step 3: will be provided with
Figure 684195DEST_PATH_IMAGE005
And tetrabutylammonium fluoride by substitution reaction
Figure 634834DEST_PATH_IMAGE006
；
And 4, step 4:
Figure 517339DEST_PATH_IMAGE006
2-mercaptoethanol and trimethylsilyl trifluoromethanesulfonate through addition reaction
Figure 869823DEST_PATH_IMAGE001
。
3. The method for preparing the hypochlorous acid fluorescent probe according to claim 2, wherein the molar ratio of 4- (methylamino) phenol sulfate, tert-butyldimethylchlorosilane to imidazole in step 1 is 1:1.2: 4.
4. The method for preparing the hypochlorous acid fluorescent probe of claim 2, wherein step 2 further comprises adding cesium carbonate, palladium acetate and 1,1 '-binaphthyl-2, 2' -bisdiphenylphosphine;
in step 2
Figure 812371DEST_PATH_IMAGE003
、
Figure 250306DEST_PATH_IMAGE002
And the molar ratio of the cesium carbonate, the palladium acetate and the 1,1 '-binaphthyl-2, 2' -bis-diphenylphosphine is 1:2:4:0.05: 0.06.
5. The method for preparing the hypochlorous acid fluorescent probe of claim 2, wherein in step 3
Figure 733240DEST_PATH_IMAGE005
And tetrabutylammonium fluoride in a molar ratio of 1: 3.
6. The method for preparing the hypochlorous acid fluorescent probe of claim 2, wherein in step 4
Figure 205810DEST_PATH_IMAGE006
The molar ratio of 2-mercaptoethanol to trimethylsilyl trifluoromethanesulfonate was 1:2: 0.1.
CN201910403158.6A 2019-05-15 2019-05-15 Hypochlorous acid fluorescent probe and preparation method thereof Active CN110016009B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910403158.6A CN110016009B (en) 2019-05-15 2019-05-15 Hypochlorous acid fluorescent probe and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910403158.6A CN110016009B (en) 2019-05-15 2019-05-15 Hypochlorous acid fluorescent probe and preparation method thereof

Publications (2)

Publication Number Publication Date
CN110016009A CN110016009A (en) 2019-07-16
CN110016009B true CN110016009B (en) 2021-05-11

Family

ID=67193746

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910403158.6A Active CN110016009B (en) 2019-05-15 2019-05-15 Hypochlorous acid fluorescent probe and preparation method thereof

Country Status (1)

Country Link
CN (1) CN110016009B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113880821B (en) * 2021-10-29 2024-03-12 南京碳硅人工智能生物医药技术研究院有限公司 Fluorescent probe design for epileptic intracerebral hypochlorous acid characteristic imaging by two-photon fluorescent probe and synthetic method thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Development of Targetable Two-Photon Fluorescent Probes to Image Hypochlorous Acid in Mitochondria and Lysosome in Live Cell and Inflamed Mouse Model;Lin Yuan;《J. Am. Chem. Soc.》;20150513;第137卷(第18期);第5930-5938页 *
Responsive mechanism of three novel hypochlorous acid fluorescent probes and solvent effect on their sensing performance;Yong Zhou;《Chin. Phys. B》;20170710;第26卷(第8期);全文 *
Two-photon fluorescent probe for peroxynitrite;JinHee Park;《Tetrahedron Letters》;20160210;第57卷(第6期);第715-718页 *

Also Published As

Publication number Publication date
CN110016009A (en) 2019-07-16

Similar Documents

Publication Publication Date Title
US9862731B2 (en) Difluoroboron dipyrromethene fluorescent probe, production method and application thereof
CN103013495B (en) Copper ion fluorescence probe and synthetic method thereof
CN110016009B (en) Hypochlorous acid fluorescent probe and preparation method thereof
CN110511203B (en) Mustard gas fluorescent probe and preparation and application thereof
Li et al. Synthesis and enantioseparation characteristics of a novel mono-6-deoxy-(2, 4-dihydroxybenzimide)-β-cyclodextrin as a chiral stationary phase in high-performance liquid chromatography
CN111825655B (en) Hg detection method2+High-sensitivity fluorescent probe and preparation method and application thereof
CN108641713A (en) A kind of fluorescence probe and its preparation method and application of detection hypochlorite ion
US11427532B2 (en) Fluorescent compound for detection of isocyanate substances, preparation method and use thereof as test-paper-type detection probe
CN114106029B (en) Organic molecule containing boron-nitrogen coordination bond and preparation method thereof
CN110128430B (en) 8-hydroxyquinolyl corrole gallium complex pH fluorescent probe and preparation method thereof
CN113121580A (en) Fluorescent probe and preparation method and application thereof
CN108489953A (en) A kind of preparation method of in-situ modification paper substrate nitro explosive fluorescent sensing material
CN110563651A (en) 1, 9-anthracene diimide compound connected with o-hydroxyl aniline and preparation method and application thereof
CN114478317B (en) Ozone fluorescent probe and preparation method and application thereof
Yang et al. Dependence of the Quantum Yield of Photoreduction of Benzophenone in 2-Propanol on Light Intensity. Possibility of Triplet Quenching by the Radical Intermediates in Solution
CN110129031A (en) A kind of fluorescence probe and the preparation method and application thereof detecting hypochlorite ion
CN108047221B (en) Perylene diimide compound, synthesis method thereof and application thereof in H 2 O 2 Application in detection
CN112028778A (en) Synthesis and impurity identification method of bromhexine hydrochloride process impurity positioning reference substance
CN105330563B (en) For the reference compound in the control of Kukoamine B quality
CN113354628B (en) 2-styryl-3-hydroxy chromone 2-thiophenecarboxylate fluorescent probe, preparation method and application thereof
CN111606854B (en) For detecting H2Isolongifolane colorimetric probe of S and preparation method thereof
CN111747898B (en) 2, 3-pindione imidazole type fluorescent probe for detecting hypochlorous acid and preparation method and application thereof
CN110563609A (en) Preparation method and application of near-infrared fluorescent probe for detecting selenious acid roots
CN115112617B (en) Fluorescent detection method for content of heavy metal cadmium in incense
CN111269120A (en) Environment-friendly preparation method of ozagrel impurity II

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
GR01 Patent grant
GR01 Patent grant