CN106350060B - A kind of response type pH value molecular probe and preparation method and purposes - Google Patents
A kind of response type pH value molecular probe and preparation method and purposes Download PDFInfo
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- CN106350060B CN106350060B CN201510418966.1A CN201510418966A CN106350060B CN 106350060 B CN106350060 B CN 106350060B CN 201510418966 A CN201510418966 A CN 201510418966A CN 106350060 B CN106350060 B CN 106350060B
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Abstract
A kind of response type pH value molecular probe and preparation method and purposes.A kind of application the invention discloses imide analog compounds as pH probes, specifically a kind of imide compound is as probe in the pH value for measuring solution；Probe preparation is simple, is easy to get, and stable structure by ultraviolet-visible absorption spectroscopy, or directly observes by the naked eye the pH value that can be quickly detected in solution for detecting solution ph；The method that the probe detects pH has high sensitivity, and selectivity is good, fast, the advantages that naked eyes are visible, can detect the pH value under strong acidic condition, have wide practical use in environmental monitoring, medical diagnosis on disease and industrial production, blowdown are examined.
Description
Technical field
The present invention relates to chemical analysis detection technique fields, and in particular to a kind of system of response type pH value molecular probe
Preparation Method and application of the molecule in terms of detecting pH value.
Background technology
Many important physiology courses are all closely related with pH value in the progress or completion of chemical reaction, organism.Therefore pH
The accurate measurement of value studies chemistry and biology all extremely important.The most commonly used is glass electrodes for existing pH value measurement method
Method.Since glass electrode method exists by electrochemistry interference, metal ion disturbance, easy mechanical damage the shortcomings of to cytoclasis, is deposited
The large error when strong acid and strong base measures, and it is unsuitable for the defects of live body pH is detected.Fluorescent spectrometry is also applied to pH value survey
In fixed, it is a kind of detection method established based on optical signalling, and with high sensitivity, selectivity is good, can carry out in real time
The advantages that in situ detection, is by higher attention.
In the prior art, although pH fluorescence probe common problems are that it is wide to the response range of hydroxide ion,
More reachable 7 pH units, are usually only applied to the physiological pH detection of pH value 6-8, and the detection for many strong basicity environment is deposited
Sensitivity is low, poor selectivity, be easy to be interfered by metal ion the defects of.Therefore, development one kind be not easy by metal from
Sub interference, narrow response range, to can be used for the fluorescence probe of measurement highly basic pH ranges be still an important research direction.
As alkaline ph values probe, structural formula is as follows for a kind of imide analog compounds：
The probe obtained by synthetic method synthesis, passes through the means such as nuclear magnetic resonance spectroscopy and carries out structure according to the literature
Verification.Probe preparation is simple, is easy to get, and stable structure.
Invention content
An object of the present invention be to provide it is a kind of it is convieniently synthesized, reaction condition is mild, lower-cost pH probe
Synthetic method；The second purpose is to provide that a kind of selectivity is good, fluorescence probe of high sensitivity, the pH value of good water solubility.
It is a further object to provide a kind of pH value assay method based on the probe.
The present invention solve the problems, such as the technical solution used for：A kind of molecular structural formula of the molecular probe of pH value：
The synthetic route of the compound of the present invention is as follows：
The specific features of pH value molecular probe of the present invention are as follows：
The molecular probe is in PBS phosphate buffers, pH=7.0) and acetonitrile mixed solution (volume ratio 90:10) molten in
Preferable, a length of 515 nm of maximum absorption wave of solution property, fluorescence signal is weaker, and solution colour is pink.After hydroxyl is added, occur
Substitution reaction, hydroxyl replace the nitryl group of probe molecule, generate phenolic compounds.With becoming larger for pH value, phenolic hydroxyl group turns
Becoming the phenol negative oxygen ion powered by force, the entire a wide range of red shift of molecular absorption wavelength generates a new absorption peak at 685 nm,
Solution colour becomes macroscopic green from pink.And the test system of other ions is added without apparent color and spectrum
Variation, shows that probe molecule can be with Selective recognition hydroxyl..
Probe molecule raw material of the present invention is easy to get, and synthetic yield is higher, and stable optical performance, sensitivity is higher, water
Dissolubility is preferable, strong to pH value recognition capability, and response speed is very fast.Therefore the type probe is in necks such as biochemistry, environmental sciences
Domain has practical application value.
Description of the drawings
Fig. 1 is the situation of change of the molecular probe ultra-violet absorption spectrum under alkaline condition of the present invention, and abscissa is wavelength,
Ordinate is absorption intensity.
Specific implementation mode
Embodiment 1：The synthesis of intermediate 1
It weighs 3.82g tetracarboxylic acid dianhydrides and 3mL cyclohexylamine is dissolved in 100mLDMF, return stirring 8 hours under nitrogen protection.
It is cooled to room temperature after complete reaction, a large amount of solids is precipitated, washed three times with distilled water, 5%KOH solution, ethanol solution respectively,
Obtain dark red solid, yield 91%.Nucleus n-ness spectrum is characterized as below：1H NMR (CDCl3), δ ppm: 8.01 (d, J = 10.8
Hz, 4H), 7.83 (d, J = 10.8 Hz, 4H), 5.01 (m, 2H), 2.53 (m, 4H), 1.92 (m, 4H),
1.75 (m, 6H), 1.44 (m, 6H)。
Embodiment 2：The preparation of fluorescence probe
1.0g intermediates 1 are measured, 1.2g ammonium ceric nitrates and 3.0mL fuming nitric aicds are dissolved in 100mL dichloromethane, in nitrogen
The lower reaction of protection 12 hours.It is neutralized to neutrality with 10%KOH, dichloromethane extraction is dry, is spin-dried for, and is elution with dichloromethane
Liquid purifies to obtain 0.67g dark red solids through silica gel chromatographic column.1H NMR(CDCl3),δppm:8.74 (d, J=6.4Hz, 1H),
8.62-8.69 (m, 4H), 8.55 (d, J=6.0Hz, 1H), 8.18 (d, J=6.0Hz, 1H), 5.00 (m, 2H), 2.54 (m,
4H),1.47-1.91(m,14H),1.34(m,2H)。
Claims (1)
1. a kind of applications of compound A as pH probes, it is characterised in that：Under alkaline condition, it is generated newly at 685 nm
Ultraviolet and visible absorption peak, there are quantitative relationships with solution ph for the UV absorption intensity of probe；The chemical molecular of the compound A
Structural formula is：
Compound A.
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| CN201510418966.1A CN106350060B (en) | 2015-07-17 | 2015-07-17 | A kind of response type pH value molecular probe and preparation method and purposes |
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| CN106350060A CN106350060A (en) | 2017-01-25 |
| CN106350060B true CN106350060B (en) | 2018-08-17 |
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