CN109470671A - One kind being used for H2The fluorescent test paper strip and its preparation and application of S detection - Google Patents

One kind being used for H2The fluorescent test paper strip and its preparation and application of S detection Download PDF

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CN109470671A
CN109470671A CN201811448246.XA CN201811448246A CN109470671A CN 109470671 A CN109470671 A CN 109470671A CN 201811448246 A CN201811448246 A CN 201811448246A CN 109470671 A CN109470671 A CN 109470671A
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detection
test paper
paper strip
fluorescent test
fluorescence probe
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赵冰
何玉倩
温景惠
阚伟
王丽艳
宋波
白雨弘旭
杨艺璇
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Qiqihar University
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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
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    • G01N21/6402—Atomic fluorescence; Laser induced fluorescence

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Abstract

The invention belongs to H2The technical field of S detection, is related to for H2The preparation of the fluorescence probe of S detection, is used for H2The fluorescent test paper strip and its preparation and application of S detection.The present invention is to solve the higher costs that vulcanization hydrogen methods are detected in existing traditional experiment room, are unable to the technical issues of real-time on-site detects hydrogen sulfide；Existing detection hydrogen sulfide fluorescence probe identification does not have specificity, the poor technical problem of anti-interference ability；The fluorescent test paper for being presently available for detection hydrogen sulfide is less, and the technical problem that complex manufacturing process is cumbersome.The structural formula of detection hydrogen sulfide fluorescence probe of the invention are as follows:The fluorescence probe uses 2- (1- phenyl -1HPhenanthro- [9,10-d] imidazoles-2-) phenol and 2,4-dinitrofluorobenzene react obtain under alkaline condition.Volume ratio be 2:8 methanol (MeOH)/N- 2- hydroxyethyl piperazine-NFluorescent test paper strip is prepared in ' -2-ethanesulfonic acid (HEPES) (pH=7.0) system.When detecting sample to be tested using the fluorescent test paper strip, if test strips are in yellow green under ultraviolet light irradiation, illustrate to contain H in solution A to be measured2S.Detection hydrogen sulfide fluorescent test paper strip of the invention can use the field of detection hydrogen sulfide.

Description

One kind being used for H2The fluorescent test paper strip and its preparation and application of S detection
Technical field
The invention belongs to H2The technical field of S detection, is related to for H2The preparation of the fluorescence probe of S detection, and it is used for H2S The fluorescent test paper strip and its preparation and application of detection.
Background technique
H2S is a kind of toxic gas with rotten egg smell, and excessive hydrogen sulfide can stimulate eyes and respiratory tract, seriously Can lead to the loss of consciousness, respiratory failure is even dead.The content of hydrogen sulfide and alzheimer's disease, Tang Shi synthesis in human body The diseases such as disease, diabetes and cirrhosis are also closely related.
Currently, for detecting H2The technology and methods of S have very much.Currently, there are many ways to detection hydrogen sulfide, such as spectrum Analytic approach, sub-methyl blue spectrum analysis, electrochemical process, gas chromatography etc., in these detection methods, wherein some methods It is cumbersome, need pre-processing to sample；Then test equipment is expensive for some, can not popularize.In comparison, fluorescence Analytic approach is easy to operate, and signal is intuitive, high sensitivity, selectivity are good, real-time in-situ detection, and is able to achieve to physiological activity cell It is imaged, therefore, has obtained the very big concern of people.Recent years, H2The detection of S have become most popular research topic it One, it there is now much about H2The report of S detection probe.
The open texts of page 8656-8658 of " chemical communication " (chemical communications) 49 phases in 2013 Chapter An ICT-based fluorescent switch-on probe for hydrogen sulfide in living Identification H is reported in cells2The technology of S, but identify H2S time more a length of 50 min, can not achieve instant detection." chemistry is logical News " (chemical communications) 49 phases in 2013 the open article A new turn-on of page 4640-4642 fluorescent probe for selective detection of glutathione and cysteine in Identification H is reported in living cells2The technology of S identifies H at 45 DEG C in the phosphate buffer that pH is 92S identifies item Part is harsh, not easy to operate.The public affairs of page 214-218 of " dyestuff and pigment " (Dyes and pigments) 110 phases in 2013 The article A highly selective fluorescent chemodosimeter for imaging hydrogen opened Designed and synthesized in sulfide in living cells it is a kind of based on fluoresceins fluorescence probe, can 2.5 ~ H is detected in 1000 μM of concentration ranges2S, but synthesis step is complicated, and five steps is needed to complete；Above several fluorescence probes identify H2S Method it is not easy to operate, it is of the present invention a kind of to be used for H2The fluorescent test paper strip of S detection can detect H immediately2S is convenient fast It is prompt.
According to current document report, sulfurated hydrogen detection is primarily present following defect:
1. H2S detection method is complicated for operation, and detection time is long, H2The volatility of S causes compared with major injury environment and human body；
2. H2S detection needs to complete by expensive equipment, higher cost；
3. H2S detection effect is not intuitive；
4. cannot achieve instant detection.
Summary of the invention
The present invention is directed to current H2S detection method is complicated for operation, and detection time is long, and testing cost is high, and detection effect is not straight See, the disadvantages of cannot achieve instant detection, provide it is a kind of have detection method simple, detection is quickly, at low cost, in real time, immediately One kind of the advantages that detection is used for H2The fluorescent test paper strip and its preparation and application of S detection.
One kind being used to prepare H2The fluorescence probe structure of the fluorescent test paper strip of S detection is as shown below:
。
It is above-mentioned to be used to prepare H2The preparation method of the fluorescence probe of the fluorescent test paper strip of S detection uses 2- (1- phenyl -1H- Phenanthro- [9,10-d] imidazoles-2-) phenol and 2,4-dinitrofluorobenzene react under alkaline condition to be obtained, and reaction equation is as follows:
It is used to prepare H2The fluorescence probe synthetic method of the fluorescent test paper strip of S detection is as follows:
By 2- (1- phenyl -1HPhenanthro- [9,10-d] imidazoles-2-) phenol and 2,4-dinitrofluorobenzene are under alkaline condition according to object The amount ratio of matter is 1: (1 ~ 3): (1 ~ 3) ratio is added in organic solvent, 25~50 DEG C of 4~6 h of stirring.After reaction, Filtering, obtains filter cake, dries.It is recrystallized again with mixed organic solvents, obtains being used to prepare H2S detection fluorescent test paper strip it is glimmering Light probe.
H is used for using the preparation of above-mentioned fluorescence probe2The preparation method of the fluorescent test paper strip of S detection, sequentially includes the following steps:
One, H will be used for2S detection fluorescence probe be dissolved in volume ratio be 2:8 methanol (MeOH)/ N- 2- ethoxy piperazine Piperazine-NIn ' -2-ethanesulfonic acid (HEPES) (pH=7.0) mixed solution, dissolve it sufficiently, being configured to concentration is 2 × 10-5 The fluorescence probe solution of mol/L；
Two, filter paper is placed into the fluorescence probe solution that step 1 obtains by the white qualitative filter paper for taking the cm of 10 cm × 10, It is taken out after sufficiently impregnating 1 ~ 2 h, dries, be cut into the test strips of the cm of 1 cm × 5, be as used for H2The fluorescent test paper strip of S detection T1；
Three, wavelength is used to hold ultraviolet light irradiation for H for 365 nm2The fluorescent test paper strip T1 of S detection, color are white Color.
It is above-mentioned to be used for H2The application method of the fluorescent test paper strip of S detection, sequentially includes the following steps:
One, solution to be measured is decolourized using active carbon, obtains colourless solution A to be measured；
Two, H will be used for2The fluorescent test paper strip T1 of S detection, which is put into solution A to be measured, sufficiently to be impregnated, and is taken out, is dried after 5 min, obtains To for H2The fluorescent test paper strip T2 of S detection；
Three, wavelength is used to hold ultraviolet light irradiation test strips T2 for 365 nm, if test strips T2 under ultraviolet light irradiation with examination The color of paper slip T1 illustrates in solution to be measured without significant difference without H2S；If under the ultraviolet light irradiation of test strips T2 being in yellow green, Then illustrate to contain H in solution A to be measured2S。
Provided by the present invention for H2The fluorescent test paper strip production method of S detection is simple, at low cost, easy to use.For H2The fluorescent test paper strip of S detection is to H2Rapidly, effect is obvious, can be used for environment and Food Chemistry field for S response.With the prior art It compares, the beneficial effects of the present invention are:
1. of the present invention be used for H2The fluorescent test paper strip of S detection is realized using the method for fluorescence enhancement to H2The identification of S with Detection；
2. of the present invention be used for H2S detection fluorescent test paper strip to H2The detection of S is limited to 7.9 × 10-8mol/L；
3. of the present invention be used for H2S detection fluorescent test paper strip to H2The detection of S has good linear relationship, can H in quantitative detection solution to be measured2S concentration；
4. of the present invention be used for H2The fluorescent test paper strip of S detection can be realized to H2The instant detection of S.
Detailed description of the invention
Fig. 1 is to be used to prepare H in MeOH/HEPES (pH=7.0) solution that volume ratio is 2:82S is detected glimmering The fluorescence probe (2.0 × 10 of light test strips-5Mol/L) and its from different analytes (2.0 × 10-4Mol/L, HS–、 AcO–、Cl–、F–、I–、H2PO4 –、HCO3 –、CO3 2–、HPO4 2–、HSO3 –、NO2 –、NO3 –、Br–、SO3 2–、S2–、SO4 2–、SCN–、BrO3 – And PO4 3–, Hcy, Gly, Thr) between fluorescence emission spectrogram of compound, abscissa is ionic species, and ordinate is fluorescence intensity level；
Fig. 2 is to be used to prepare H in MeOH/HEPES (pH=7.0) solution that volume ratio is 2:82The fluorescence examination of S detection The fluorescence probe (2.0 × 10 of paper slip-5Mol/L) in other anion (2.0 × 10-4Mol/L, AcO–、Cl–、F–、 I–、H2PO4 –、HCO3 –、CO3 2–、HPO4 2–、HSO3 –、NO2 –、NO3 –、Br–、SO3 2–、S2–、SO4 2–、SCN–、BrO3 –And PO4 3–、Hcy、 Gly, Thr) in the presence of, HS is added–Ion (2.0 × 10-4Mol/L fluorescence intensity) compares bar chart, horizontal seat It is designated as ionic species, ordinate is fluorescence intensity；
Fig. 3 is to be used to prepare H in MeOH/HEPES (pH=7.0) solution that volume ratio is 2:82The fluorescence examination of S detection The fluorescence probe (2.0 × 10 of paper slip-5Mol/L the sulphur hydrogen radical ion (0~10 × 10 of low concentration) is added-6Mol/L after) Stern-Volmer straight line；
Fig. 4 is to be used to prepare H2The fluorescent test paper strip of S detection is in detection H2Before and after S, use wavelength ultraviolet for holding for 365 nm The color change figure of light irradiation test strips.
Specific embodiment
Specific embodiment 1: present embodiment is used to prepare H2The fluorescence probe structure of the fluorescent test paper strip of S detection Formula are as follows:
。
Specific embodiment 2: being used to prepare H described in specific embodiment one2The fluorescence of the fluorescent test paper strip of S detection Probe preparation method sequentially includes the following steps:
By 2- (1- phenyl -1HPhenanthro- [9,10-d] imidazoles-2-) phenol and 2,4-dinitrofluorobenzene are under alkaline condition according to object The amount ratio of matter is 1: (1 ~ 3): (1 ~ 3) ratio is added in organic solvent, 25~50 DEG C of 4~6 h of stirring.After reaction, Filtering, obtains filter cake, dries.It is recrystallized, is obtained for H with the mixed solvent of ethyl acetate and petroleum ether again2The fluorescence of S detection The fluorescence probe of test strips.
Specific embodiment 3: present embodiment is used for H unlike specific embodiment two2The fluorescence examination of S detection Organic solvent acetonitrile, methylene chloride, chloroform, acetone or tetrahydrofuran described in the fluorescence probe synthesis condition of paper slip Any one of.
Specific embodiment 4: present embodiment is used for H unlike specific embodiment two or three2S is detected glimmering Alkaline matter described in the fluorescence probe synthesis condition of light test strips is K2CO3Solid, Na2CO3Solid or Na2SO4Solid, KOH solid, NaOH solid or NaHCO3Any one of solid；It is other to be identical with embodiment two.
Specific embodiment 5: present embodiment is used to prepare H unlike specific embodiment two, three or four2S inspection The fluorescence probe post-processing organic solvent recrystallized used of the fluorescent test paper strip of survey be ethyl acetate and petroleum ether by volume For 1:(1 ~ 5) mixed liquor, ethyl acetate and n-hexane be by volume 1:(1 ~ 5) mixed liquor or ethyl acetate and dichloro Methane is 1:(1 ~ 5 by volume) any one of mixed liquor.It is other identical as specific embodiment two to three.
Specific embodiment 6: the preparation method of HEPES buffer solution are as follows: useN- 2- hydroxyethyl piperazine-N' -2-ethanesulfonic acid 0.60 g is put into the volumetric flask of 250 mL, with distilled water constant volume, is made into the solution of 0.01 mol/L, is shaken up, after static 3 h, With sodium hydroxide solution tune pH value, it is made into the buffer solution that pH value is 7.0~12.0 and is made into pH value with nitric acid solution tune pH value For 3.0~6.0 buffer solution.
Specific embodiment 7: being used for H described in specific embodiment one2The preparation method of the fluorescent test paper strip of S detection, is pressed Following methods carry out:
One, H will be used for2S detection fluorescence probe be dissolved in volume ratio be 2:8 methanol (MeOH)/ N- 2- ethoxy piperazine Piperazine-NIn ' -2-ethanesulfonic acid (HEPES) (pH=7.0) mixed solution, dissolve it sufficiently, being configured to concentration is 2 × 10-5 The fluorescence probe solution of mol/L；
Two, filter paper is placed into the fluorescence probe solution that step 1 obtains by the white qualitative filter paper for taking the cm of 10 cm × 10, It is taken out after sufficiently impregnating 1 ~ 2 h, dries, be cut into the test strips of the cm of 1 cm × 5, be as used for H2The fluorescent test paper strip of S detection T1；
Three, wavelength is used to hold ultraviolet light irradiation for H for 365 nm2The fluorescent test paper strip T1 of S detection, color are white Color.
Specific embodiment 8: being used for H described in specific embodiment one2The application method of the fluorescent test paper strip of S detection, is pressed Following methods carry out:
By fluorescent test paper strip T1 prepared by specific embodiment six, it is used for H2The fluorescent test paper strip T2 of S detection is placed at room temperature It is that holding for 365 nm observes the fluorescence colors of two test strips under ultraviolet light irradiation in wavelength after dry 10 min.If test paper T2 under ultraviolet light irradiation with the color of test strips T1 without significant difference, illustrate in solution to be measured without H2S；If test strips T2 It is in yellow green under ultraviolet light irradiation, then illustrates to contain H in solution A to be measured2S。
With following case verification beneficial effects of the present invention:
Embodiment 1: the present embodiment is used for H2The preparation method of the fluorescence probe of the fluorescent test paper strip of S detection, by the following method It carries out:
By 2- (1- phenyl -1HPhenanthro- [9,10-d] imidazoles -2-) phenol, K2CO3Solid, 2,4-dinitrofluorobenzene are according to substance Amount ratio be 1: 1.5: 3 ratio be added in acetonitrile solvent, 5 h are stirred at 25 DEG C.After reaction, it filters, is eaten with saturation Salt water washing filter cake, drying, then recrystallized crude product with the mixed solvent that the volume ratio of ethyl acetate and n-hexane is 1: 3, It obtains for H2The fluorescence probe of the fluorescent test paper strip of S detection.For H2The fluorescence probe yield of fluorescent test paper strip of S detection is 90%, fusing point is 220~223 DEG C.
It is characterized with infrared spectroscopy and nuclear magnetic resoance spectrum, it is as follows to obtain result:
IR (KBr, cm–1): 3058, 2928, 1605, 1576, 1067, 761. 1H NMR (600 MHz, DMSO ) δ: 8.91 (d, J = 8.47 Hz 1H, ArH), 8.84 (d, J = 7.26 Hz , 1H, ArH), 8.69 (s,1H, ArH), 8.51 (d, J = 8.16 Hz , 1H, ArH), 8.27 (t, J=6.6 Hz, 1H, ArH), 7.56~ 7.70 (m, 10H, ArH), 7.34~70 (m, 3H, ArH), 7.08 (t, 2H, ArH)
It is as follows from the structural formula of the available fluorescence probe manufactured in the present embodiment of above data:
。
H is used for by manufactured in the present embodiment2The fluorescence probe of the fluorescent test paper strip of S detection carries out spectrum property test:
One, the configuration of stock solution
It will be used for H first2The fluorescence probe of the fluorescent test paper strip of S detection is that solvent is configured to main body deposit with methanol (MeOH) Liquid；Wherein H is detected in main body stock solution2The concentration of S fluorescence probe is 1.0 × 10-4~3.0 × 10-4mol/L；
The HEPES buffer solution that main body stock solution concentration is 0.01 mol/L, pH=7.0 is diluted again, it is molten to obtain probe Liquid A1；Wherein probe solution A1Middle detection H2The concentration of S fluorescence probe is 1 × 10-5~3×10-5mol/L；
The configuration of HEPES buffer solution: weigh 0.60 g'sN- 2- hydroxyethyl piperazine-NThe appearance of 250 mL is added in ' -2-ethanesulfonic acid It in measuring bottle, with distilled water constant volume, is made into the solution of 0.01 mol/L and shakes up, after static 3 h, with sodium hydroxide solution tune pH Value, being made into pH value is 7.0 buffer solutions.It shakes up, it is spare.
Two, spectrum property is tested
It is above-mentioned to be used for H2The fluorescence probe of the fluorescent test paper strip of S detection detects H2The method of S, mainly comprises the steps that
It is 2 × 10 that concentration is added into 10 mL volumetric flasks-4The fluorescence probe stock solution of mol/L, adding concentration is 0.10 Anion to be measured, Hcy, Gly, Thr of mol/L, the HEPES buffer solution constant volume for being 0.01 mol/L, pH=7 with concentration.This When, fluorescence probe and H2The concentration ratio of the amount of the substance of S is 1:10,2 h to 37 DEG C of constant temperature, carries out the survey of fluorescence emission spectrum Examination.
In MeOH/HEPES buffer solution (v/v=2/8, pH=7.0) system, fluorescence probe is investigated to anion Selective recognition.When excitation wavelength is 329 nm, the fluorescence intensity of fluorescence probe is measured.Again to fluorescence probe solution In be separately added into concentration be 2.0 × 10-4The HS of mol/L–、AcO–、Cl–、F–、I–、H2PO4 –、HCO3 –、CO3 2–、HPO4 2–、 HSO3 –、NO2 –、NO3 –、Br–、SO3 2–、S2–、SO4 2–、SCN–、BrO3 –And PO4 3–, after Hcy, Gly, Thr, and it is strong to survey fluorescence respectively Degree.As a result as shown in Figure 1, the launch wavelength of fluorescence probe is in 480 nm or so, fluorescence intensity is in 2.30 a.u..AcO is added–、 Cl–、F–、I–、H2PO4 –、HCO3 –、CO3 2–、HPO4 2–、HSO3 –、NO2 –、NO3 –、Br–、SO3 2–、S2–、SO4 2–、SCN–、BrO3 –And PO4 3– After anion and Hcy, Gly, Thr, the fluorescence intensity of fluorescence probe does not change substantially, and HS is added–Afterwards, fluorescence intensity increases By force to 33 a.u. or so.Enhance 15 times that intensity is fluorescence probe.Therefore, from the point of view of fluorescence emission spectrum, fluorescence probe pair H2S has selection recognition performance.
For further verify this experiment preparation for H2The evident characteristics of the fluorescence probe of the fluorescent test paper strip of S detection, In MeOH/HEPES buffer solution (v/v=2/8, pH=7.0) system, first it is separately added into fluorescence probe solution dense Degree is 2.0 × 10-4The AcO of mol/L–、Cl–、F–、I–、H2PO4 –、HCO3 –、CO3 2–、HPO4 2–、HSO3 –、NO2 –、NO3 –、Br–、 SO3 2–、S2–、SO4 2–、SCN–、BrO3 –And PO4 3–It is 2.0 that concentration is added after anion and Hcy, Gly, Thr, after sufficient standing 5min × 10-4 mol/L HS–Solution.Fluorescence probe/other analyte/HS at this time–The substance withdrawl syndrome ratio of three is 1:10: 10.2 h to 37 DEG C of constant temperature, when excitation wavelength is 329 nm, the test of fluorescence emission spectrum is carried out to it.Obtain result As shown in Fig. 2, in other anion (AcO–、Cl–、F–、I–、H2PO4 –、HCO3 –、CO3 2–、HPO4 2–、HSO3 –、NO2 –、NO3 –、Br–、 SO3 2–、S2–、SO4 2–、SCN–、BrO3 –And PO4 3–) with Hcy, Gly, Thr Coexistence Situation under, HS–It is glimmering when being coexisted with other analytes Light probe and HS–Identification is not influenced by other anion and molecule.Fig. 2 illustrates fluorescence probe to H2S identification has single-minded identification Characteristic.
H is used for by induction and conclusion2The fluorescence probe fluorescence intensity change and H of the fluorescent test paper strip of S detection2S concentration becomes The relationship of change, with I/I0(HS is added in fluorescence probe–Fluorescence intensity/fluorescence probe fluorescence intensity) be ordinate, with HS–It is dense Degree is abscissa, draws Stern-Volmer straight line.As shown in figure 3,0~1.0 × 10-5In mol/L concentration range, fluorescence The variation of intensity be used for H2S detection fluorescent test paper strip fluorescence probe concentration show good linear relationship, it can be achieved that To H2The quantitative detection of S.The equation of linear regression being fitted is y=0.3796x+0.8452, R2=0.9932, wherein y is indicated HS is added in fluorescence probe–Fluorescence intensity and fluorescence probe fluorescence intensity ratio, x indicate HS–Concentration, unit 10-6mol/ L。
It is manufactured in the present embodiment to be used for H2The fluorescence probe of the fluorescent test paper strip of S detection, in MeOH/HEPES buffer solution In the system of (v/v=2/8, pH=7.0), H is detected by Enhancement of Fluorescence2S, and when other metal ions coexist, no Interfere the probe to H2The detection of S；By comparing fluorescent test paper strip T1, it is used for H2S detection fluorescent test paper strip T2 hold it is ultraviolet Fluorescence color under the irradiation of lamp proves to contain H in sample to be tested if the color of fluorescent test paper strip T2 is yellow green2S。
Embodiment 2: embodiment 1 is replaced the present embodiment with following operation unlike the first embodiment: by 2- (1- phenyl- 1HPhenanthro- [9,10-d] imidazoles-2-) phenol, KOH solid, 2,4-dinitrofluorobenzene according to the mass ratio of the material be 1: 1.5: 1.5 ratio Example is added in tetrahydrofuran solvent, and 4 h are stirred at 40 DEG C.After reaction, it filters, with saturated common salt water washing filter cake, Drying, then recrystallized crude product with the mixed solvent that the volume ratio of ethyl acetate and petroleum ether is 1: 4, it obtains for H2S inspection The fluorescence probe of the fluorescent test paper strip of survey.For H2The fluorescence probe yield of the fluorescent test paper strip of S detection is 85%, fusing point 220 ~223 DEG C.
Embodiment 3: embodiment 1 is replaced the present embodiment with following operation unlike the first embodiment: by 2- (1- phenyl- 1HPhenanthro- [9,10-d] imidazoles -2-) phenol, Na2CO3Solid, 2,4-dinitrofluorobenzene are 1: 1: 3 ratio according to the mass ratio of the material It is added in acetone solvent, 5 h is stirred at 50 DEG C.After reaction, it filters, with saturated common salt water washing filter cake, dries, Crude product is recrystallized with the mixed solvent that the volume ratio of ethyl acetate and petroleum ether is 1: 4 again, is obtained for H2S is detected glimmering The fluorescence probe of light test strips.The yield of the probe is 75%.Fusing point: 220~223 DEG C.
Embodiment 4: embodiment 1 is replaced the present embodiment with following operation unlike the first embodiment: by 2- (1- phenyl- 1HPhenanthro- [9,10-d] imidazoles -2-) phenol, Na2SO4Solid, 2,4-dinitrofluorobenzene are 1: 1.5: 3 ratio according to the mass ratio of the material Example is added in chloroform solvent, and 6 h are stirred at 30 DEG C.After reaction, it filters, with saturated common salt water washing filter cake, Drying, then recrystallized crude product with the mixed solvent that the volume ratio of ethyl acetate and n-hexane is 1: 4, it obtains for H2S inspection The fluorescence probe of the fluorescent test paper strip of survey.The yield of the probe is 80%.Fusing point: 220~223 DEG C.
Embodiment 5: embodiment 1 is replaced the present embodiment with following operation unlike the first embodiment: by 2- (1- phenyl- 1H- phenanthro- [9,10-d] imidazoles -2-) phenol, NaHCO3Solid, 2,4-dinitrofluorobenzene are 1: 1.5: 2 according to the mass ratio of the material Ratio is added in acetone solvent, and 5 h are stirred at 45 DEG C.After reaction, it filters, with saturated common salt water washing filter cake, dries It is dry, then recrystallized crude product with the mixed solvent that the volume ratio of ethyl acetate and petroleum ether is 1: 4, it obtains for H2S detection Fluorescent test paper strip fluorescence probe.The yield of the probe is 70%.Fusing point: 220~223 DEG C.
Embodiment 6: embodiment 1 is replaced the present embodiment with following operation unlike the first embodiment: by 2- (1- phenyl- 1HPhenanthro- [9,10-d] imidazoles-2-) phenol, KOH solid, 2,4-dinitrofluorobenzene according to the mass ratio of the material be 1: 1: 1.5 ratio It is added in acetonitrile solvent, 4 h is stirred at 40 DEG C.After reaction, it filters, with saturated common salt water washing filter cake, dries, then Crude product is recrystallized with the mixed solvent that the volume ratio of ethyl acetate and petroleum ether is 1: 4, is obtained for H2The fluorescence of S detection The fluorescence probe of test strips.For H2The fluorescence probe yield of the fluorescent test paper strip of S detection is 75%, and fusing point is 220~223 DEG C.
Embodiment 7: embodiment 1 is replaced the present embodiment with following operation unlike the first embodiment: 2- (1- phenyl -1H- Phenanthro- [9,10-d] imidazoles-2-) phenol, NaOH solid, 2,4-dinitrofluorobenzene according to the mass ratio of the material be 1: 1.5: 3 ratio add Enter into chloroform solvent, 6 h are stirred at 25 DEG C.After reaction, it filters, with saturated common salt water washing filter cake, dries, Crude product is recrystallized with the mixed solvent that the volume ratio of ethyl acetate and n-hexane is 1: 3 again, is obtained for H2S is detected glimmering The fluorescence probe of light test strips.The yield of the probe is 80%.Fusing point: 220~223 DEG C.
Embodiment 8: embodiment 1 is replaced the present embodiment with following operation unlike the first embodiment: by 2- (1- phenyl- 1HPhenanthro- [9,10-d] imidazoles -2-) phenol, Na2CO3Solid, 2,4-dinitrofluorobenzene are 1: 2: 3 ratio according to the mass ratio of the material It is added in acetonitrile solvent, 4 h is stirred at 50 DEG C.After reaction, it filters, with saturated common salt water washing filter cake, dries, then Crude product is recrystallized with the mixed solvent that the volume ratio of ethyl acetate and methylene chloride is 1: 5, is obtained for H2S is detected glimmering The fluorescence probe of light test strips.The yield of the probe is 70%.Fusing point: 220~223 DEG C.

Claims (7)

1. one kind of present embodiment is used to prepare H2The fluorescence probe structural formula of the fluorescent test paper strip of S detection are as follows:
。
2. described in claim 1 be used to prepare H2The fluorescence probe of the fluorescent test paper strip of S detection, sequentially includes the following steps:
By 2- (1- phenyl -1HPhenanthro- [9,10-d] imidazoles-2-) phenol and 2,4-dinitrofluorobenzene are under alkaline condition according to object The amount ratio of matter is 1: (1 ~ 3): (1 ~ 3) ratio is added in organic solvent, 25~50 DEG C of 4~6 h of stirring.After reaction, Filtering, obtains filter cake, dries.It is recrystallized again with mixed organic solvents, obtains being used to prepare H2S detection fluorescent test paper strip it is glimmering Light probe.
3. as claimed in claim 2 be used to prepare H2The fluorescence probe of the fluorescent test paper strip of S detection, it is characterised in that be used for H2S inspection Organic solvent acetonitrile described in the fluorescence probe synthesis condition of the fluorescent test paper strip of survey, methylene chloride, chloroform, acetone, Or any one of tetrahydrofuran.
4. as claimed in claim 2 be used to prepare H2The fluorescence probe of the fluorescent test paper strip of S detection, it is characterised in that be used for H2S inspection Alkaline matter described in the fluorescence probe synthesis condition of the fluorescent test paper strip of survey is K2CO3Solid, Na2CO3Solid or Na2SO4 Solid, KOH solid, NaOH solid or NaHCO3Any one of solid.
5. as claimed in claim 2 be used to prepare H2The fluorescence probe of the fluorescent test paper strip of S detection, it is characterised in that be used for H2S inspection Crude product recrystallization solvent described in the fluorescence probe synthesis condition of the fluorescent test paper strip of survey is the acetic acid second that organic solvent is Ester and petroleum ether are 1:(1 ~ 5 by volume) mixed liquor, ethyl acetate and n-hexane be by volume 1:(1 ~ 5) mixed liquor Either ethyl acetate and methylene chloride is 1:(1 ~ 5 by volume) any one of mixed liquor.
6. being used to prepare H using described in claim 12The preparation of the fluorescent test paper strip of S detection sequentially includes the following steps:
One, H will be used for2S detection fluorescence probe be dissolved in volume ratio be 2:8 methanol (MeOH)/ N- 2- hydroxyethyl piperazine-NIn ' -2-ethanesulfonic acid (HEPES) (pH=7.0) mixed solution, dissolve it sufficiently, being configured to concentration is 2.0 × 10-5 The fluorescence probe solution of mol/L；
Two, filter paper is placed into the fluorescence probe solution that step 1 obtains by the white qualitative filter paper for taking the cm of 10 cm × 10, It is taken out after sufficiently impregnating 1 ~ 2 h, dries, be cut into the test strips of the cm of 1 cm × 5, be as used for H2The fluorescent test paper strip of S detection T1；
Three, wavelength is used to hold ultraviolet light irradiation for H for 365 nm2The fluorescent test paper strip T1 of S detection, color are white.
7. being used to prepare H using described in claim 12The application method of the fluorescent test paper strip of S detection sequentially includes the following steps:
One, solution to be measured is decolourized using active carbon, obtains colourless solution A to be measured；
Two, H will be used for2The fluorescent test paper strip T1 of S detection, which is put into solution A to be measured, sufficiently to be impregnated, and is taken out, is dried after 5 min, obtains To for H2The fluorescent test paper strip T2 of S detection；
Three, wavelength is used to hold ultraviolet light irradiation test strips T2 for 365 nm, if test strips T2 under ultraviolet light irradiation with examination The color of paper slip T1 illustrates in solution to be measured without significant difference without H2S；If under the ultraviolet light irradiation of test strips T2 being in yellow green, Then illustrate to contain H in solution A to be measured2S。
CN201811448246.XA 2018-11-30 2018-11-30 One kind being used for H2The fluorescent test paper strip and its preparation and application of S detection Pending CN109470671A (en)

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