CN106317062A - Preparing and application of ratio-type fluorescence probe for measuring cadmium ion - Google Patents
Preparing and application of ratio-type fluorescence probe for measuring cadmium ion Download PDFInfo
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Abstract
The invention discloses a ratio-type fluorescence probe for measuring cadmium ion and preparing method and application thereof. The method includes dissolving 5,10,15,20- tetraphenylporphyrin, 2- 2- pyridine methyl amine (DPA), potassium iodide and potassium carbonate in acetonitrile based on the molar ratio of 1:4:4:4, heating them to backflow under the protection of nitrogen, reacting for 6-9 hours and obtaining target cadmium ion fluorescence probe (PD) through silica gel chromatograph separation. The probe has simple preparing method, moderate conditions and convenient post-processing, and displays double changes of colorimetric and ratio fluorescence when detecting cadmium ion with convenient detection process and accurate results.
Description
Technical field
The present invention relates to the preparation of a kind of Ratiometric fluorescent probe measuring cadmium ion, be specifically related to a kind of with two-2-pyrroles
Pyridine methyl amine (DPA) be recognition group, Porphyrin Molecule be the preparation method of the fluorescent probe of fluorescent chromophore, and this probe divides
Son is applied to colorimetric and the Ratio-type fluoroscopic examination of cadmium ion in solution.
Background technology
Along with the fast development of modernization industry, heavy metal ion pollution becoming serious.Wherein, cadmium is a kind of toxicity
The strongest heavy metal, due to cadmium ion (Cd2+) there is bioconcentration, long half time (twenty or thirty year), should not decompose
Feature, enters human body upon biological chain and is enriched with in vivo, can cause people's pulmonary function disorder, renal insufficiency, calcium metabolism
Disorderly, skeletal injury and be greatly increased the probability suffering from cancer.In recent years, there is a lot of cadmium pollution events, wherein most typically in China
Be that the Hunan rice cadmium content occurred for 2013 exceeds standard event, caused the strong interest that cadmium ion is polluted by people.China
Cadmium pollution preventing and treating has been classified as " 13 planning " key special subjects by government.People are in the urgent need to quick, accurate, low cost and can select
The method analyzing to selecting property detection cadmium ion.Therefore, site environment detection method, mobile laboratory and portable instrumentation etc.
Concept is proposed by many research worker in recent years.Wherein, by colorimetry or the chemical sensitisation method with fluorescence as output signal
The most prominent.
At present, report the most in a large number based on small-molecule fluorescent probe method detection cadmium ion, but the fluorescent probe being typically designed
It is usually expressed as fluorescence radiation-cancellation (on-off) or fluorescent quenching-recovery is luminous (off-on), i.e. glimmering in same transmitting peak position
Light intensity changes.The problems such as it is high that this response modes also exists detection background, and signal disturbing is serious.Porphyrin
(Porphyrin) to be a class by four pyrrole rings be connected by the methine Conjugate macrocycle compound constituted, has high fluorescence
Quantum yield, big Stokes displacement, relatively long excite and launch wavelength, and good light stability, sensitive to microenvironment, it is one
The near-infrared fluorescent chromophore signaling molecule of class excellent performance, is widely used in the structure of photochemistry molecular probe.Porphyrin chemical combination
The easy modified of thing can make its macro ring periphery couple different substituent groups and active function groups, by MOLECULE DESIGN and chemical reaction
It can be combined from different recognition units, synthesize a series of optical physics and the adjustable functional probe of spectrochemical property, be applied to
(Coordination Chemistry Reviews 1999,190-192:683-706 in various detection fields；Talanta
2000,51:209-224；Sensors and Actuators B:Chemical 2013,179:21-31.).Porphyrin compound
Excellent optical property, the colorimetric/fluorescence that can realize extremely low concentration ion quickly detects, and majority shows as the fluorescence of Ratio-type
Respondent behavior: i.e. using the ratio of two emission peak intensity as detection signal, this pattern can be effectively reduced environmental change pair
Impact in fluorescence signal so that detection process has higher specificity (Sensors 2013,13:3131-3141；
Sensors 2013,13:15758-15769)。
Therefore, can by Molecular Design cleverly, by Porphyrin Molecule with some can Selective recognition cadmium ions point
Subelement combines, and changes whole molecular structure, thus change connected porphyrin chromophore after utilizing this unit and cadmium ion complexation
The Photophysics of molecule realizes the Sensitive Detection to cadmium ion.
Summary of the invention
The present invention is directed to the problems such as preparation complexity, bad response and the ambient interferences existing for existing fluorescent probe is serious,
Provide a kind of with the two Ratio-type cadmium ions that-2-picolyl amine (DPA) is as recognition group, Porphyrin Molecule is as fluorescent chromophore
Fluorescent probe and preparation method thereof.
The Ratio-type cadmium ion fluorescent probe (PD) that the present invention provides, has a following general structure:
The preparation method of a kind of Ratio-type cadmium ion fluorescent probe (PD), comprises the steps:
By 5,10,15,20-tetrabromo phenyl porphyrin, two-2-picolyl amine (DPA), potassium iodide, potassium carbonate with 1:4:4:4
Mol ratio be dissolved in organic solvent, nitrogen protection under, be heated to backflow, react 6～9h, silica gel chromatography isolated target cadmium
Ion fluorescence probe (PD).
The preparation method of described Ratio-type cadmium ion fluorescent probe (PD), specifically includes following steps:
(1) commercially available four (4-aminophenyl) porphyrin (TATPP) are dissolved in concentrated hydrochloric acid, form the solution of 0.03mmol/mL,
Dropwise instill sodium nitrite in aqueous solution under ice bath, react 10min；Then it is added dropwise over potassium iodide aqueous solution, continues reaction 20min
After, it is warming up to room temperature, reacts 2.5h.It is 8 that product ammonia is neutralized to pH, use dichloromethane extraction, organic layer wash with water to
Neutrality, reduce pressure steaming vibrating dichloromethane.Thick product silica gel chromatographic column separates, and dichloromethane is developing solvent, collects the first colour band and produces
Thing, obtains 5,10,15,20-tetrabromos phenyl porphyrin (TBrTPP).
The structural formula of TATPP is:
The structural formula of TBrTPP is:
(2) by 5,10,15,20-tetrabromo phenyl porphyrin (TBrTPP), two-2-picolyl amine (DPA), potassium iodide, carbonic acid
Potassium is dissolved in organic solvent with the mol ratio of 1:4:4:4, the volume of organic solvent and 5, the amount of 10,15,20-tetrabromo phenyl porphyrins
Being directly proportional, keeping 5,10,15,20-tetrabromo phenyl porphyrins concentration in the solution is 0.01mmol/mL.It is heated to reflux, reacts 6
～after 9h, using thin layer chromatography (TLC) checking without 5,10,15,20-tetrakisaminophenyl porphyrin starting material left, silica gel chromatography divides
From thick product, collect the first colour band product.
In described step (1), the concentrated hydrochloric acid solution concentration of TATPP is 0.03mmol/mL, the concentration of sodium nitrite in aqueous solution
For 0.2mmol/mL, the concentration of kbr aqueous solution is 0.2mmol/mL, and choosing of these ratios can ensure that all raw materials are molten
Agent can fully be dissolved, be beneficial to reaction and efficiently carry out.
In described step (1), the concentrated hydrochloric acid solution of TATPP: sodium nitrite in aqueous solution: the volume ratio of kbr aqueous solution is excellent
Selecting 33:5:5, experiment to show, this ratio can ensure that amino diazo-reaction is the most abundant, it is to avoid anti-from coupling reaction and other pairs
The generation answered, promotes TATPP greater efficiency to be converted into TBrTPP.
Organic solvent in described step (2) is acetonitrile.
The boiling point that the heating-up temperature being heated to reflux is acetonitrile (about 76 DEG C) in described step (2).
In described step (2), plate chromatography developing solvent is dichloromethane: methanol=9:1 (volume ratio).
In described step (2), silica gel chromatography separation developing solvent is dichloromethane: methanol=9:1 (volume ratio).
5,10,15,20-tetrabromo phenyl porphyrin, two-2-picolyl amine (DPA), potassium iodide, carbonic acid in described step (2)
The mol ratio of potassium is preferably 1:4:4:4, and experiment shows, this ratio peak efficiency can promote 5,10,15,20-tetrabromo phenyl porphyrins
It is converted into end product PD, it is to avoid the generation of by-product.
The volume and 5 of organic solvent in described step (2), the amount of 10,15,20-tetrabromo phenyl porphyrins is directly proportional, and keeps 5,
10,15,20-tetrabromo phenyl porphyrins concentration in the solution is 0.01mmol/mL, and this ratio can make reaction raw materials at solvent
Can the most fully dissolve in the case of consumption is minimum, be more conducive to reaction and fully carry out.
In described step (2), the response time is 6～9h, and the mark that reaction terminates is to use thin layer color described in step (2)
Spectrometry (TLC) is verified without 5,10,15,20-tetrakisaminophenyl porphyrin starting material left.
Described Ratio-type cadmium ion fluorescent probe (PD) can occur distinctive complexation reaction (as follows) with cadmium ion.
Described Ratio-type cadmium ion fluorescent probe (PD) can cause the color of porphyrin signal group with cadmium ion after being coordinated
Change and fluorescent emission occur that Ratio-type responds.
Present invention have the advantage that
(1) synthetic method of the cadmium ion fluorescent probe (PD) of the present invention, mild condition, step are simple, and post processing is easy；
(2) present invention uses Porphyrin Molecule as signal reporter group, and this molecule is near-infrared fluorescent chromophore molecule, light
Learn excellent performance, sensitive to microenvironment, bigger Stocks displacement can be obtained, enhance the sensitivity of reaction signal；
(3) cadmium ion fluorescent probe (PD) of the present invention can demonstrate the doubling sensitivity of colorimetric/fluorescence to cadmium ion
Matter, can realize the quick detection of Trace Cadmium ion by naked eyes or fluorescence spectrophotometer, highly sensitive；
(4) cadmium ion fluorescent probe (PD) of the present invention is Ratio-type to the fluorescence response of cadmium ion, can effectively drop
Low environment change is for the impact of fluorescence signal so that detection process has higher specificity and accuracy.
Accompanying drawing explanation
Fig. 1 is cadmium ion fluorescent probe of the present invention (PD)1H NMR spectra；
Fig. 2 is the fluorescence spectrum figure of cadmium ion fluorescent probe of the present invention (PD)；
Fig. 3 is the color variation diagram before and after cadmium ion fluorescent probe of the present invention (PD) adds cadmium ion；
Fig. 4 is the cadmium ion titration fluorescence spectrogram of cadmium ion fluorescent probe of the present invention (PD).
Detailed description of the invention
Embodiment 1
Commercially available four (4-aminophenyl) porphyrin (TATPP) (675mg, 0.10mmol) is dissolved in 33mL concentrated hydrochloric acid, ice bath
Under dropwise instill the sodium nitrite in aqueous solution (NaNO of 5mL2Concentration be 0.2mmol/mL), react 10min；Then it is added dropwise over
5mL kbr aqueous solution (concentration of KBr is 0.2mmol/mL), after continuing reaction 20min, is warming up to room temperature, reacts 2.5h.Produce
It is 8 that thing ammonia is neutralized to pH, uses dichloromethane extraction, and organic layer washes with water to neutrality, and reduce pressure steaming vibrating dichloromethane, vacuum
2h it is dried in drying baker.Thick product silica gel chromatographic column separates, and dichloromethane is developing solvent, collects the first colour band product, obtains
5,10,15,20-tetrabromo phenyl porphyrin (TBrTPP).
By 5,10,15,20-tetrabromo phenyl porphyrin (TBrTPP) (93mg, 0.1mmol), two-2-picolyl amine (DPA)
(70.5 μ L, 0.4mmol), potassium iodide (66.7mg, 0.4mmol), potassium carbonate (55.2mg, 0.4mmol) are dissolved in 10mL acetonitrile,
After heating reflux reaction 8h, use thin layer chromatography (TLC) (developing solvent ratio dichloromethane: methanol=9:1 (v/v)), checking
Without after 5,10,15,20-tetrakisaminophenyl porphyrin starting material left, rotary evaporation of solvent, silica gel chromatography separates thick product (developing solvent
Ratio dichloromethane: methanol=9:1 (v/v)), collect the first colour band product.Employing proton nmr spectra (1H NMR) (Fig. 1) with
And fluorescence spectrum (Fig. 2) verifies its chemical constitution.1The solvent of H NMR uses deuterated DMSO (DMSO-d6), the ginseng of fluorescence spectrophotometer
Number is as follows: excitation wave wavelength is 420nm；Receiving wave-wave section is 600nm～725nm.
Application examples 1
Fluorescent probe (PD) is to the colorimetric detection of cadmium ion in solution: owing to cadmium ion can be coordinated with PD, cause porphyrin to believe
Number group generation color change, therefore can will add isocyatic cadmium-ion solution, naked eyes in certain density PD molecular solution
Observe the color change of PD solution.Detailed process is as follows: be dissolved in DMSO by PD, is made into the solution that concentration is 10 μMs, by chlorine
Cadmium is dissolved in distilled water, is made into the solution of 10 μMs.In 5mL seed bottle, add above-mentioned PD solution 0.4mL (10 μMs), add 10
μM Caddy (Cleary) aqueous solution 0.4mL, use DMSO dilution be settled to 4.0mL, after standing 5 minutes, perusal solution colour change
Changing, result is as shown in Figure 3.From figure 3, it can be seen that Cd2+The color that can cause PD solution is changed into green by pink, illustrates that PD visits
The colorimetric detection of naked eyes can be realized for cadmium ion.
Application examples 2
Fluorescent probe (PD) is to the fluorescence titration of variable concentrations cadmium ion in solution: be dissolved in DMSO by PD, is made into dense
Degree is the solution of 10 μMs；Caddy (Cleary) is dissolved in distilled water, is made into the aqueous solution of variable concentrations.PD is added molten in 10mL volumetric flask
After liquid 1.0mL (10 μMs), then the cadmium ion aqueous solution 1.0mL, employing DMSO that are separately added into variable concentrations dilute and are settled to
10.0mL, after standing 5 minutes, uses fluorescence spectrometry to add the change in fluorescence spectrogram of variable concentrations cadmium ion.Result such as Fig. 4
Shown in.
The parameter of fluorescence spectrophotometer is as follows: excitation wave wavelength is 420nm；Receiving wave-wave section is 620nm～720nm.
Claims (6)
1. the Ratiometric fluorescent probe measuring cadmium ion, it is characterised in that the structural formula of described probe molecule is as follows:
2. measure a preparation method for the Ratiometric fluorescent probe of cadmium ion, comprise the steps:
By 5,10,15,20-tetrabromo phenyl porphyrin, two-2-picolyl amine (DPA), potassium iodide, potassium carbonate rubbing with 1:4:4:4
You are dissolved in organic solvent by ratio, under nitrogen protection, are heated to backflow, react 6～9h, silica gel chromatography isolated target cadmium ion
Fluorescent probe (PD).
The preparation method of a kind of Ratiometric fluorescent probe measuring cadmium ion the most according to claim 2, it is characterised in that
Described organic solvent is acetonitrile.
The preparation method of a kind of Ratiometric fluorescent probe measuring cadmium ion the most according to claim 2, it is characterised in that
5,10,15,20-tetrabromo phenyl porphyrin concentration in the solution is 0.01mmol/mL.
The preparation method of a kind of Ratiometric fluorescent probe measuring cadmium ion the most according to claim 2, it is characterised in that
The boiling point that heating-up temperature is acetonitrile of reaction.
PD fluorescence prepared by the preparation method of a kind of Ratiometric fluorescent probe measuring cadmium ion the most as claimed in claim 2 is visited
Pin application to Trace Cadmium ion Ratio-type fluoroscopic examination in the solution.
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| CN110320195A (en) * | 2019-08-21 | 2019-10-11 | 合肥工业大学 | A kind of colorimetric fluorescence probe and its preparation method and application |
| CN113267464A (en) * | 2021-06-17 | 2021-08-17 | 江苏大学 | Method and device for detecting multi-component heavy metal in edible oil based on near infrared combined colorimetric sensor array |
| CN113968864A (en) * | 2020-07-23 | 2022-01-25 | 浙大城市学院 | Cu based on zinc porphyrin axial coordination regulation+Fluorescent probe, preparation method and application |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110320195A (en) * | 2019-08-21 | 2019-10-11 | 合肥工业大学 | A kind of colorimetric fluorescence probe and its preparation method and application |
| CN113968864A (en) * | 2020-07-23 | 2022-01-25 | 浙大城市学院 | Cu based on zinc porphyrin axial coordination regulation+Fluorescent probe, preparation method and application |
| CN113968864B (en) * | 2020-07-23 | 2023-04-07 | 浙大城市学院 | Cu based on zinc porphyrin axial coordination regulation + Fluorescent probe, preparation method and application |
| CN113267464A (en) * | 2021-06-17 | 2021-08-17 | 江苏大学 | Method and device for detecting multi-component heavy metal in edible oil based on near infrared combined colorimetric sensor array |
| CN113267464B (en) * | 2021-06-17 | 2024-06-07 | 江苏大学 | Method and device for detecting multi-component heavy metals in edible oil based on near infrared combined colorimetric sensor array |
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