CN110283100A - A kind of compound, preparation method and the application as hydrazine fluorescence probe - Google Patents
A kind of compound, preparation method and the application as hydrazine fluorescence probe Download PDFInfo
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- CN110283100A CN110283100A CN201910655237.6A CN201910655237A CN110283100A CN 110283100 A CN110283100 A CN 110283100A CN 201910655237 A CN201910655237 A CN 201910655237A CN 110283100 A CN110283100 A CN 110283100A
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- 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"
- G01N2021/6443—Fluorimetric titration
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Abstract
The disclosure belongs to small organic molecule fluorescence probe field, and in particular to a kind of compound, preparation method and the application as hydrazine fluorescence probe.Hydrazine is widely used in multiple fields as a kind of common industrial reagent.But hydrazine has stronger toxicity, and can enter human body by steam or skin and cause organic damage.The technology detected using fluorescent probe compounds to hydrazine is disclosed in the prior art, but there are also many limitations in practical applications for presently disclosed fluorescent probe compounds.Present disclose provides a kind of hydrazine fluorescent detection probe of structure novel, which has good detection sensitivity, strong interference immunity, can work in liquid environment in the range of pH6~12, can be prepared as Test paper and be applied, and has good dissemination.
Description
Technical field
The disclosure belongs to small organic molecule fluorescence probe field, and in particular to a kind of novel compound, the compound
The application of preparation method and the compound as hydrazine detection fluorescence probe.
Background technique
The information for disclosing the background technology part is merely intended to increase the understanding to the general background of the disclosure, without certainty
It is considered as recognizing or implying in any form that information composition has become existing skill well known to persons skilled in the art
Art.
Hydrazine, also known as hydrazine (NH2NH2), it is one that highly polar compound can be miscible in water, alcohol isopolarity solvent well
The important industrial reagent of kind, is widely used in the fields such as catalysis, pesticide, polymer, fuel cell and agricultural.As a kind of high
Energy fuel, hydrazine play an important role in rocket propulsion system.But research shows that hydrazine can pass through with very strong toxicity
Sucking steam or skin contact enter human body, to cause serious harm to kidney, central nervous system, liver and lung.In life
When producing, transport, store, shifting or handle related waste, producers are likely to suck or percutaneously contact the substance.Separately
Outside, since hydrazine is soluble easily in water, it is easy to cause water pollution.American National Environmental Protection Agency provides that the content of hydrazine in drinking water is no more than
10ppb.Based on factors above, develop a kind of with highly sensitive and method that is highly selective and being capable of fast detection of trace hydrazine
It is necessary.Fluorescent probe technique because it is highly sensitive, highly selective, easy to operate, can real-time monitoring the features such as by
Extensive concern is arrived.A kind of fluorescence probe for detecting hydrazine hydrate and its preparation side are provided in patent CN108689962A
Method, the compounds process for production thereof is simple but more demanding to the pH of working environment, needs to work under the conditions of pH7-8, practical
Application range is narrow.
Summary of the invention
For the studies above background, the disclosure can be used for the fluorescence probe of hydrazine detection in order to further expand, and obtain one kind
Detection sensitivity is high, interference free performance is more preferable, and the probe for being applicable to various water bodies environment expands research.It is studied through the disclosure
A kind of probe of structure novel, and the probe function admirable are obtained, Test paper can be prepared as, there is good popularization meaning
Justice.
In order to achieve the above technical purposes, the following technical schemes are provided:
For the disclosure in a first aspect, providing a kind of compound, the compound structure such as following formula (I) is shown:
Present disclose provides a kind of isophorone derivatives of structure novel, can be used as detection of the fluorescence probe for hydrazine.
Research shows that the probe molecule itself is in dimethyl sulfoxide and PBS
(pH=7.4) there is no fluorescence in mixed solution (volume ratio 9:1), be added after hydrazine, occur fluorescence at 630nm
Peak, and peak intensity enhances with the increase of hydrazine content.The disclosure further study showed that, in Na+, K+, Ca2+, Mg2+, Fe2+,
Fe3+, Cu2+, Zn2+, Ni2+, Ag+, Hg2+, Br-, I-, SO4 2-, CO3 2-, HCO3 -, HSO3 -, SO3 2-, S2O3 2-, NO2 -, OAc-, NO3 -,
BrO3 -, IO4 -, NH2In the presence of the chaff interferents such as OH, EDA, probe shows very high selectivity to hydrazine, has anti-interference well
Ability.In addition, by verifying, above compound can have good fluorescence intensity in the solution in 6~12 range of pH value.
Disclosed hydrazine fluorescence probe compared to the prior art, compound described in first aspect have good detection sensitivity and anti-dry
Ability is disturbed, and can adapt to the solution environmental of different pH value, is a kind of detection probe compound with function admirable.
Disclosure second aspect provides a kind of preparation method of compound, and the preparation method comprises the following steps: will
(E) -2- (3- (2- (6- hydroxynaphenyl -2- base) vinyl) -5,5,-dimethyleyelohexane -2- alkene -1- subunit) malononitrile and acetyl
Chlorine reacts to obtain compound described in first aspect, and the synthetic route of the preparation method is as follows:
Preferably, the reaction dissolvent system is methylene chloride and triethylamine mixed system.
It is further preferred that (E) -2- (3- (2- (6- hydroxynaphenyl -2- base) vinyl) -5, the 5,-diformazan basic ring
Hex- 2- alkene -1- subunit) malononitrile and chloroacetic chloride, triethylamine feed intake according to 0.5~1.5:1 of molar ratio~3:4~6.
Preferably, the reaction carries out at room temperature.
Preferably, the reaction time is 1~3h.
The disclosure third aspect provides a kind of test paper, compound described in the test paper load first aspect.
The compound that the disclosure provides, which can be carried on filter paper, becomes Test paper, and when detection immerses test paper to be measured molten
In liquid, after taking-up can naked eye test paper color change, and under 365nm ultraviolet lamp observe test paper change in fluorescence, it is glimmering
Hydrazine content is higher in the higher proof solution of luminous intensity.
Disclosure fourth aspect, provides the preparation method of test paper described in the third aspect, and the preparation method includes following step
It is rapid: filter paper to be placed in the organic solvent of compound described in first aspect, dry to obtain the test paper.
Preferably, the organic solvent is methylene chloride.
The 5th aspect of the disclosure provides application of the compound described in first aspect as hydrazine detection fluorescence probe.
The 6th aspect of the disclosure provides test paper described in compound and/or the third aspect described in first aspect in hydrazine and detects neck
The application in domain.
Compared with prior art, the beneficial effect of the disclosure is:
1. present disclose provides a kind of isophorone derivative hydrazine fluorescent probe compounds, disclosed compared to the prior art
Hydrazine fluorescence probe, the compound in the disclosure have novel main ring structure, and under different ions disturbed condition, in wider pH
It still is able to show good detection effect in the solution of range, has widened applicable water body environment significantly.
2. the disclosure additionally provides the Test paper for loading above-mentioned biological hydrazine fluorescent probe compounds, test paper preparation process
Simply, using simplicity, test paper need to only be immersed in solution to be measured during actually detected, by naked eye or in purple after taking-up
Fluorescence intensity is observed under outer light, there is good application value.
Detailed description of the invention
The Figure of description for constituting a part of this disclosure is used to provide further understanding of the disclosure, and the disclosure is shown
Meaning property embodiment and its explanation do not constitute the improper restriction to the disclosure for explaining the disclosure.
Fig. 1 is fluorescence intensity figure of the compound before and after hydrazine is added in embodiment 1；
Wherein, reaction system is the DMSO-PBS solution (9:1, volume ratio, pH=7.4) of compound (10 μM)；Curve a is
Fluorescence curve of the compound before hydrazine is added, b are fluorescence curve of the compound after hydrazine is added.
Fig. 2 is fluorescence intensity figure of the compound under different ions disturbed condition in embodiment 1；
Wherein, reaction system is the DMSO-PBS solution (9:1, volume ratio, pH=7.4) of compound (10 μM), is added 50
Fluorescence intensity histogram after equivalent hydrazine and 100 equivalent disturbance objects, ordinate are the fluorescence intensity at 630nm.
Fig. 3 is the change in fluorescence figure that compound carries out hydrazine titration in embodiment 1；
Wherein, reaction system is the DMSO-PBS solution (9:1, volume ratio, pH=7.4) of compound (10 μM), from 0~
The change in fluorescence of 500 μM of progress hydrazine fluorescence titration.
Fig. 4 is the figure of fluorescence intensity changes of compound under different ph values in embodiment 1；
Wherein, compound concentration is 10 μM, fluorescence intensity change when adding hydrazine and hydrazine is not added at 630nm.
Fig. 5 is color and change in fluorescence figure of the Test paper in the presence of various concentration hydrazine in embodiment 2.
Specific embodiment
It is noted that following detailed description is all illustrative, it is intended to provide further instruction to the disclosure.Unless another
It indicates, all technical and scientific terms used herein has usual with disclosure person of an ordinary skill in the technical field
The identical meanings of understanding.
It should be noted that term used herein above is merely to describe specific embodiment, and be not intended to restricted root
According to the illustrative embodiments of the disclosure.As used herein, unless the context clearly indicates otherwise, otherwise singular
Also it is intended to include plural form, additionally, it should be understood that, when in the present specification using term "comprising" and/or " packet
Include " when, indicate existing characteristics, step, operation, device, component and/or their combination.
As background technique is introduced, hydrazine is a kind of important industrial reagent, is had a wide range of applications in multiple fields.
Since hydrazine has good water solubility, human body can be entered by steam or skin contact, since hydrazine has toxicity, provided sensitive
Hydrazine detection means is of great significance.In order to solve technical problem as above, the present disclosure proposes a kind of hydrazine detection small molecule is glimmering
Light probe, the fluorescence probe.
In order to enable those skilled in the art can clearly understand the technical solution of the disclosure, below with reference to tool
The technical solution of the disclosure is described in detail in the embodiment and comparative example of body.
Embodiment 1
The synthesis of probe
170mg (0.5mmol) compound 1 and 253mg (2.5mmol) triethylamine are dissolved in the dry methylene chloride of 10mL,
Ice bath is cooled to 0 DEG C, and 78mg (1.0mmol) chloroacetic chloride is added dropwise, and reaction 2 hours is warmed to room temperature after adding.Crude product is concentrated under reduced pressure to obtain.
118mg orange solids are obtained by silica gel column chromatography (4:1, petroleum ether-ethyl acetate) purifying, yield: 62%.
By infrared, hydrogen spectrum, carbon spectrum and Mass Spectrometer Method formula (I) compound, following structural information is obtained:
Infrared spectroscopy IR (KBr) ν: 3445,2962,2209,1748,1636,1562,1523,1367,1340,1226,
1140,1012,967,887,808,663,471cm-1
Hydrogen spectrum1H-NMR(400MHz,DMSO-d6) δ (ppm): 8.17 (s, 1H), 7.99-7.87 (m, 3H), 7.66 (d, J=
2.3Hz, 1H), 7.55 (d, J=16.2Hz, 1H), 7.43 (d, J=16.2Hz, 1H), 7.34 (dd, J=8.8,2.3Hz, 1H),
6.92(s,1H),2.61(s,2H),2.58(s,2H),2.32(s,3H),1.02(s,6H)；
Carbon spectrum13C NMR(101MHz,DMSO-d6)δ(ppm):168.99,168.67,153.18,148.82,136.32,
133.84,132.65,130.96,129.40,129.01,128.19,128.08,123.60,123.25,121.61,118.20,
112.98,78.33,76.71,42.51,38.82,31.56,27.54,20.71；
High resolution mass spectrum HRMS calcd for [M+H]+C25H23N2O2:383.1754,found 383.1750。
50 equivalents are added into the DMSO-PBS solution (9:1, volume ratio, pH=7.4) of formula (I) compound (10 μM)
Hydrazine, compared with hydrazine is not added, the fluorescence at 630nm is remarkably reinforced, as shown in Figure 1.
50 equivalents are separately added into the DMSO-PBS solution (9:1, volume ratio, pH=7.4) of formula (I) compound (10 μM)
Hydrazine and 100 equivalents other chaff interferents, test its fluorescence intensity change at 630nm.The results show that be added disturbance from
In the case where son, the fluorescence intensity of the compound solution is consistent substantially, it was demonstrated that interfering ion has no effect on compound to hydrazine
Fluorescence response, formula (I) compound to hydrazine have good selectivity and anti-interference ability, as shown in Figure 2.
Different equivalents are added into the DMSO-PBS solution (9:1, volume ratio, pH=7.4) of formula (I) compound (10 μM)
Hydrazine tests the fluorescence intensity change at its 630nm, and when 50 equivalent hydrazine is added, fluorescence intensity reaches maximum, as shown in Figure 3.
Under different ph values, the solution of test formula (I) compound (10 μM) 630nm when adding hydrazine and hydrazine being not added
The fluorescence intensity change at place.As shown in figure 4, solution ph is in 6~12 ranges, which all shows higher
Fluorescence intensity, it was demonstrated that the fluorescent probe compounds are suitable for wider pH range.
Embodiment 2
The compound prepared in embodiment 1 is dissolved in methylene chloride, is configured to the solution that concentration is 1mM.Filter paper is immersed
It takes out, dries after the solution, obtain the test paper of probe load.Configuration concentration is respectively 0,1%, 2.5%, 5%, 10% hydrazine
Aqueous solution takes out, naked eye test paper color change after test paper is immersed hydrazine solution, and test paper is observed under 365nm ultraviolet lamp
Change in fluorescence, as shown in Figure 5.
The foregoing is merely preferred embodiment of the present disclosure, are not limited to the disclosure, for the skill of this field
For art personnel, the disclosure can have various modifications and variations.It is all within the spirit and principle of the disclosure, it is made any to repair
Change, equivalent replacement, improvement etc., should be included within the protection scope of the disclosure.
Claims (10)
1. a kind of compound, which is characterized in that shown in the compound structure such as following formula (I):
2. a kind of preparation method of compound, which is characterized in that the preparation method comprises the following steps: by (E) -2- (3- (2-
(6- hydroxynaphenyl -2- base) vinyl) -5,5,-dimethyleyelohexane -2- alkene -1- subunit) malononitrile and excess acetyl chloride obtain the
On the one hand the synthetic route of the compound, the preparation method is as follows:
3. the preparation method of compound as claimed in claim 2, which is characterized in that the reaction dissolvent system be methylene chloride with
Triethylamine mixed system.
4. the preparation method of compound as claimed in claim 3, which is characterized in that (E) -2- (3- (2- (the 6- hydroxynaphenyl -
2- yl) vinyl) -5,5,-dimethyleyelohexane -2- alkene -1- subunit) malononitrile and chloroacetic chloride, triethylamine according to molar ratio 0.5~
1.5:1~3:4~6 feed intake.
5. the preparation method of compound as claimed in claim 2, which is characterized in that the reaction carries out or described at room temperature
Reaction time is 1~3h.
6. a kind of test paper, which is characterized in that compound described in the test paper load claim 1.
7. the preparation method of test paper described in claim 6, which is characterized in that the preparation method comprises the following steps: by filter paper
It is placed in the organic solvent of compound described in claim 1, dries to obtain the test paper.
8. the preparation method of test paper as claimed in claim 7, which is characterized in that the organic solvent is methylene chloride.
9. application of the compound described in claim 1 as hydrazine detection fluorescence probe.
10. test paper described in compound or claim 6 described in claim 1 is in the application of hydrazine detection field.
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Cited By (3)
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| CN111484470A (en) * | 2020-03-28 | 2020-08-04 | 齐鲁工业大学 | Fluorescent probe for detecting hydrazine, preparation method and application thereof |
| CN114933555A (en) * | 2022-06-24 | 2022-08-23 | 西北大学 | Near-infrared fluorescent probe for detecting micromolecular mercaptan and preparation method thereof |
| CN115894293A (en) * | 2022-12-15 | 2023-04-04 | 枣庄学院 | Ratiometric near-infrared fluorescent probe for detecting hydrazine, and synthetic method and application thereof |
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| CN109897041A (en) * | 2019-03-13 | 2019-06-18 | 江苏科技大学 | A kind of near-infrared zinc ion fluorescent compound and its preparation method and application |
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| CN109897625A (en) * | 2017-12-08 | 2019-06-18 | 南京理工大学 | Selective enumeration method cysteine fluorescence probe and its synthetic method and application |
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| HONGSHUI LV ET AL.: "A novel dicyanoisophorone based red-emitting fluorescent probe with a large Stokes shift for detection of hydrazine in solution and living cells", 《SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY》 * |
| KHAC HONG NGUYEN ET AL.: "Recent progress in the development of fluorescent probes for hydrazine", 《LUMINESCENCE》 * |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111484470A (en) * | 2020-03-28 | 2020-08-04 | 齐鲁工业大学 | Fluorescent probe for detecting hydrazine, preparation method and application thereof |
| CN114933555A (en) * | 2022-06-24 | 2022-08-23 | 西北大学 | Near-infrared fluorescent probe for detecting micromolecular mercaptan and preparation method thereof |
| CN115894293A (en) * | 2022-12-15 | 2023-04-04 | 枣庄学院 | Ratiometric near-infrared fluorescent probe for detecting hydrazine, and synthetic method and application thereof |
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Application publication date: 20190927 |