CN103242329A - 9-fluorene-N'-(rhodamine 6G-hydrazide)pH fluorescence molecular probe as well as preparation method and use thereof - Google Patents
9-fluorene-N'-(rhodamine 6G-hydrazide)pH fluorescence molecular probe as well as preparation method and use thereof Download PDFInfo
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Abstract
The invention discloses a 9-fluorene-N'-(rhodamine 6G-hydrazide)pH fluorescence molecular probe as well as a preparation method and use thereof. Under the action of hydrogen ion induction, a rhodamine 6G lactam spiral ring in the compound is changed into a fluorescent open ring state from a colorless closed state, and therefore, the color of the solution is changed into orange red from achromatic color with fluorescence emission; in addition, strong fluorescent light is generated under the action of exciting light with a certain wavelength. The compound I can be used for high-selectivity naked eye coloration identification for hydrogen ions and also used as a fluorescent identifying probe.
Description
The present invention carries out under the subsidy of Tianjin Normal University's development fund (fund number for 52XK1102).
Technical field
The invention belongs to the chemical sensitisation technical applications, relate to compound 9-fluorenes-
N 'The preparation method of-(rhodamine 6G-hydrazides), and compound I is to the bore hole colour developing identification of hydrogen ion highly selective and the purposes of fluorescence identification probe.
Background technology
The carrying out of chemical reaction or finish, the many important physiological process of cell and organoid is all closely related with the pH value, and the mensuration of pH value has very important meaning.The method of measuring pH at present is a lot, as colorimetry, electrode method and optical pickocff etc.The sensitivity of colorimetry is lower, can not satisfy the detection that small pH in the life system is changed, and therefore can't be applied to the life system carries out the active somatic cell radiography.As pH glass electrode method known to us certain limitation is arranged, for example, can produce electrical interference or damage cell for the mensuration of cellular pH, so they do not fit into internal pH and microscopy.Compare with electrochemical method, do not have these defectives based on the photochemical method of fluorescent probe.[Ogikubo?S,?Nakabayashi?T,?Adachi?T,?Islam?MS,?Yoshizawa?T,?Kinjo?M,?
et?al.Intracellular?pH?sensing?using?auto?fl?uorescence?lifetime?microscopy?[J]?PhysChem?B?2011;115(34):10385-90.]。PH fluorescent probe analytical procedure has characteristics such as selectivity is good, highly sensitive, sample size is little, simple and efficient.
The compound I that this patent is invented is a kind of pH fluorescent molecular probe based on rhodamine 6G, has imines C=N double bond structure, rhodamine 6G lactan spirocyclic compound in this compound has the characteristics of " closed-colourless ", " open loop-coloured and generation fluorescence ", can carry out fluorescence identification to hydrogen ion.Experiment shows that compound I has the purposes to the bore hole colour developing identification of hydrogen ion highly selective and fluorescence identification probe, and not disturbed by metal ion.
The compound that has the I constitutional features as mentioned above of inventor's design is the new compound that does not appear in the newspapers.
Summary of the invention
First purpose of the present invention has provided has compound in structural formula I and preparation method thereof.
Second purpose of the present invention provided inclusion compound I and has been used for the bore hole colour developing identification of hydrogen ion highly selective and the purposes of fluorescence identification probe.
The invention discloses following technology contents for achieving the above object:
Have compound in structural formula I 9-fluorenes-
N '-(rhodamine 6G-hydrazides):
The present invention further discloses compound 9-fluorenes-
N 'The preparation method of-(rhodamine 6G-hydrazides), the preparation of compound I is carried out as follows:
(1) preparation of raw material rhodamine 6G hydrazides
(2) target compound is synthetic
Round-bottomed flask is put in rhodamine 6G hydrazides and the Fluorenone mixing of above-mentioned preparation, add methanol solution, and add several glacial acetic acids as catalyzer, with mixed system reflux 5-6 hour, monitor with thin-layer chromatography, be down to room temperature after question response is finished, the mixed system in the flask is poured in the frozen water, use the triethylamine regulator solution to pH=8, suction filtration, and with distilled water wash precipitation 2-3 time, the thick product of gained separates through column chromatography, obtain structural formula and be the compound 9-fluorenes of I-
N '-(rhodamine 6G-hydrazides).Wherein the mol ratio of rhodamine 6G hydrazides and Fluorenone is 1.25: 1.
The present invention further discloses compound I as the application to hydrogen ion highly selective bore hole colour developing identification and fluorescence identification probe aspect.
The compound that the present invention is designed
Molecular characterization be that in the structure of I the xanthene lactan volution of rhodamine 6G is closure state, solution is colourless, when hydrogen ion and compound
Do the time spent, volution is opened, and this moment, solution became orange red and with fluorescent emission by colourless.Therefore, compound
Can carry out fluorescence identification to hydrogen ion.Experiment shows that compound I has the purposes to the bore hole colour developing identification of hydrogen ion highly selective and fluorescence identification probe.
The positively effect that compound I disclosed in this invention compared with prior art has is:
(1) safe preparation process is synthetic simple;
(2) have advantages such as highly sensitive, highly selective and rapid reaction;
(3) this fluorescent molecular probe is not subjected to Mg when detecting hydrogen ion
2+, Ca
2+, Mn
2+, Fe
3+, Co
2+, Ni
2+, Cu
2+, Zn
2+, Sr
2+, Cd
2+, Ba
2+, Hg
2+, Pb
2+, Bi
3+Isoionic interference.
Description of drawings:
Fig. 1 is the structural formula of compound I;
Fig. 2 is 10
μThe tetrahydrofuran (THF) of M compound I: water=4: 6 (v: the ultra-violet absorption spectrum of pH value of solution=1.1-12.9 v), wherein, X-coordinate is represented wavelength, ordinate zou Abs is absorption intensity;
Fig. 3 is 10
μThe tetrahydrofuran (THF) of M compound I: water=4: 6 (v: the fluorescence emission spectrum of pH value of solution=1.1-12.9 v), wherein, X-coordinate is represented wavelength, ordinate zou F.I. is fluorescent emission intensity;
Fig. 4 is 10
μThe tetrahydrofuran (THF) of M compound I: water=4: 6 (v: the uv-absorbing of pH value of solution=1.1-12.9 v) and different metal ion, wherein, X-coordinate is represented wavelength, ordinate zou Abs is absorption intensity;
Fig. 5 is 10
μThe tetrahydrofuran (THF) of M compound I: (v: pH value of solution=1.1-12.9 v) reaches water=4: 6
The fluorescence emission spectrum of different metal ion, wherein, X-coordinate is represented wavelength, ordinate zou F.I. is fluorescent emission intensity;
Fig. 6 is compound
Mass spectrum;
Fig. 7 is 10
μThe tetrahydrofuran (THF) of M compound I: (v: v) solution is 10 for water=4: 6
μImaging contrast under the existence of M nicotinic acid and blank (right side among the figure) natural light;
Fig. 8 is 10
μThe tetrahydrofuran (THF) of M compound I: (v: v) solution is 10 for water=4: 6
μImaging contrast under the existence of M nicotinic acid and blank (right side among the figure) ultraviolet lamp.
Embodiment:
In order to explain enforcement of the present invention more fully, provide following preparation method's embodiment.These embodiments only are to explain rather than limit the scope of the invention.For simple and clear, in below discussing the description of technique known method, the process for preparation of solution are repeated no more.Raw material rhodamine 6G wherein has commercially available.
Compound
Synthetic:
(1) raw material rhodamine 6G hydrazides is synthetic
1.5 g rhodamine 6Gs are dissolved in the 30 mL ethanol, add in the flask of 100 mL, the hydrazine hydrate that at room temperature adds 2.4 mL 80% to mixed system stirred 30 minutes, then mixture heating up was refluxed, when solution is become clarification orange by scarlet, reaction finishes, and is cooled to room temperature, revolves the steaming desolventizing, get product 1.3g, productive rate 87.6%.
(2) target compound is synthetic
1.0 g rhodamine 6G hydrazides and 0.3 g Fluorenone are added in the 100 mL flasks, and add 6 mL methyl alcohol solid is dissolved, dripping 4-6 again drips glacial acetic acid and makees catalyzer, with the mixed system reflux to complete reaction, after finishing, question response is down to room temperature, mixed system in the flask is poured in the beaker that fills trash ice, with the triethylamine regulator solution to pH=8, suction filtration, and with distilled water wash precipitation 2-3 time, the thick product of gained separates (methylene dichloride: methyl alcohol=20: 1 v: v), obtain target compound 0.87 g, productive rate 79.6% through column chromatography.
1H-NMR?(400?MHz,?DMSO)?δ:?7.963?(d,?
J?=?7.1?Hz,?1H),?7.770?(t,?
J?=8.4,?2H),?7.679?–?7.603?(m,?2H),?7.527?(d,?
J?=?7.6?Hz,?1H),?7.45?(dd,?
J?=?18.8,?7.4?Hz,?2H),?7.347?(t,?
J?=?7.6?Hz,?1H),?7.252?(dt,?
J?=?14.5,?7.1?Hz,?2H),?7.171?(d,?
J?=?7.1?Hz,?1H),?6.329?(s,?2H),?6.250?(s,?2H),?5.015?(t,?
J?=?4.9?Hz,?2H),?3.133?–?3.070?(m,?4H),?1.820?(s,?6H),?1.188?(t,?
J?=?7.0?Hz,?6H)。
13C?NMR?(101?MHz,?DMSO)?δ(ppm):?162.027,?160.833,?151.784,?148.006,?142.220,?140.591,?136.435,?134.053,?132.357,?132.102,?131.378,?129.761,?129.128,?128.810,?128.638,?128.065,?124.502,?123.917,?122.761,?121.706,?120.762,?118.296,?105.847,?96.079,?68.025,?55.384,?37.931,?17.464,?14.635。
MS?(ESI-MS)，
m/z，591.4?[M+H]
+?。
The synthetic route of above reaction process is as follows:
Embodiment 2.
Compound
Synthetic:
(1) raw material rhodamine 6G hydrazides is synthetic
6.0 g rhodamine 6Gs are dissolved in the 120 mL ethanol, add in the flask of 250 mL, the hydrazine hydrate that at room temperature adds 9.6 mL 80% to mixed system stirred 30 minutes, then mixture heating up was refluxed, when solution is become clarification orange by scarlet, reaction finishes, and is cooled to room temperature, revolves the steaming desolventizing, get product 4.6 g, productive rate 79.1%.
(2) target compound is synthetic
With 3.0 g rhodamine 6G hydrazides and 1.0 g Fluorenones, add in the 100 mL flasks, and add 18 mL methyl alcohol solid is dissolved, drip 0.3 mL glacial acetic acid again and make catalyzer, with the mixed system reflux to complete reaction, after finishing, question response is down to room temperature, mixed system in the flask is poured in the beaker that fills trash ice, with the triethylamine regulator solution to pH=8, suction filtration, and with distilled water wash precipitation 2-3 time, the thick product of gained is through column chromatography separation (methylene dichloride: methyl alcohol=20: 1 v: v), obtain target compound 2.34 g, productive rate 72.5%.
Embodiment 3
Compound
Synthetic:
(1) raw material rhodamine 6G hydrazides is synthetic
10.0 g rhodamine 6Gs are dissolved in the 190 mL ethanol, add in the flask of 250 mL, the hydrazine hydrate that at room temperature adds 16.0 mL 80% to mixed system stirred 30 minutes, then mixture heating up was refluxed, when solution is become clarification orange by scarlet, reaction finishes, and is cooled to room temperature, revolves the steaming desolventizing, get product 7.1 g, productive rate 72.3%.
(2) target compound is synthetic
With 6.0 g rhodamine 6G hydrazides and 2.0 g Fluorenones, add in the 100 mL flasks, and add 36 mL methyl alcohol solid is dissolved, dripping 0.6 mL again drips glacial acetic acid and makees catalyzer, with the mixed system reflux to complete reaction, after finishing, question response is down to room temperature, mixed system in the flask is poured in the beaker that fills trash ice, with the triethylamine regulator solution to pH=8, suction filtration, and with distilled water wash precipitation 2-3 time, the thick product of gained is through column chromatography separation (methylene dichloride: methyl alcohol=20: 1 v: v), obtain target compound 4.09 g, productive rate 62.5%.
Compound I to the hydrogen ion recognition performance:
With compound
Preparing 10 mL concentration is 1.0 * 10
-3MolL
-1Tetrahydrofuran (THF):
Tris(v: v), the solution of pH=7.5 is as storing solution for-HCl=4: 6.The preparation tetrahydrofuran (THF): water=4: 6 (v: v), pH is respectively 1.1,2.0, and 3.1,4.0,5.1,6.1,6.9,8.1,9.0,10.0,11.0,12.1,12.9 solution.Determine that by UV spectrum, fluorescence spectrum this compound can identify the hydrogen ion in the strong acid solution.
Concrete operations are:
Get 0.1 mL compound of above-mentioned preparation
Solution, respectively with solution dilution to 10 mL, 1.0 * 10 of 13 kinds of different pH values of above-mentioned preparation
-5MolL
-1, measure compound respectively
UV spectrum, the fluorescence spectrum of 13 kinds of different pH value.
UV spectrum, fluorescence spectrum are seen Fig. 2 and Fig. 3 with the relation of different pH values.Test shows, compound
Intensity at strong acid solution medium ultraviolet absorption spectrum and fluorescence emission spectrum is very strong, and very weak in the intensity of slightly acidic and basic solution medium ultraviolet absorption spectrum, fluorescence emission spectrum; Increase with hydrogen ion concentration in pH reduction, the system, the intensity of ultra-violet absorption spectrum, fluorescence emission spectrum significantly strengthens, and the uv-absorbing of the solution of pH=1.1-3.1 maximum absorption occurs at 540 nm, and fluorescence emission spectrum peak value occurs at 580 nm, simultaneously, compound
The solution of pH=1.1-3.1 become orange redly by colourless, and the solution of other pH does not have colour-change.Therefore, compound
Hydrogen ion had good selectivity.
Embodiment 5.
When compound I is identified hydrogen ion, Mg
2+, Ca
2+, Mn
2+, Fe
3+, Co
2+, Ni
2+, Cu
2+, Zn
2+, Sr
2+, Cd
2+, Ba
2+, Hg
2+, Pb
2+, Bi
3+The ELIMINATION OF ITS INTERFERENCE of 14 metal ion species:
According to embodiment 4 methods preparation compound I, above-mentioned 14 kinds of tested metal ion solution.At first configuration concentration is 1.0 * 10
-3MolL
-1Storing solution, use 13 kinds of different pH solution that compound I is diluted to 10 mL, 1.0 * 10 during test
-5MolL
-1Solution, metal ion solution is diluted to 10 mL, 5.0 * 10
-5MolL
-1Solution, measure compound respectively
With Mg
2+, Ca
2+, Mn
2+, Fe
3+, Co
2+, Ni
2+, Cu
2+, Zn
2+, Sr
2+, Cd
2+, Ba
2+, Hg
2+, Pb
2+, Bi
3+The ultra-violet absorption spectrum of metal ion solution, fluorescence emission spectrum.Compound
See Fig. 4 and Fig. 5 with UV spectrum, the fluorescence spectrum relation of hydrogen ion, tested metal ion.Test shows, compound
With the ultra-violet absorption spectrum of the solution of 12 metal ion species, fluorescence emission spectral intensity extremely a little less than, reduce with pH, the intensity of ultra-violet absorption spectrum, fluorescence emission spectrum significantly strengthens, fluorescence emission spectrum with the uv-absorbing of 540 nm peak values and 580 nm peak values appears respectively in the solution of pH=1.1-3.1, simultaneously, compound
The solution of pH=1.1-3.1 become orange redly by colourless, and the solution of other pH does not have colour-change, and the existence of metal ion is not disturbed hydrionic identification.Therefore, in the presence of tested metal ion, compound
Hydrionic identification had good selectivity.
The practical application of embodiment 6. compound I
Along with progress of science and technology and development, solve practical problems with the integrated approach of multidisciplinary intersection and become more and more important.For example, the many important physiological process of cell and organoid is all closely related with the pH value, and the mensuration of pH value has very important meaning.The method of measuring pH at present is a lot, as colorimetry, electrode method etc.But its application aspect biology all exists certain limitation.For example poor sensitivity, poor stability, interfering factors are many etc.
Based on the pH value of the fluorescence molecule spectrographic technique detection architecture of fluorescent probe, compare with traditional method, have advantage such as highly sensitive, that selectivity good, resolving power is high, be convenient to operate, the reaction times is fast and be subjected to general attention.Reported some fluorescent pH probes, for most of pH fluorescent molecular probes, the scope of a very big problem detection all is very wide usually, and this has just lowered the sensitivity of probe.[Baruah?M,?Qin?WW,?Basaric?N,?Borggraeve?WMD,?Boens?N.?BODIPY-based?hydroxyaryl?derivatives?as?fluorescent?pH?probes.?[J]?
Org.?Chem.?2005,?70(10),?4152-7]。Yet, as far as we know, seldom paid close attention to for the fluorescent probe of (pH＜4) in the low pH scope.For example, the physiological function of nicotinic acid in living organism is be to transmit the carrying electronics, makes end vasorelaxation action and lipogenesis etc. slightly.If human body lacks nicotinic acid, can cause symptoms such as fatigue, headache, backache; But hyperphagia can produce certain side effect, and for example, skin is red itches, the serum uric acid value raises, glucose tolerance impairment and produce infringement to liver.Therefore, for aspects such as medicine, healthcare products, needing the pH value of a kind of pKa with nicotinic acid=2.2 is the fluorescent probe of monitoring objective, to develop the application that the nicotinic acid content of above-mentioned system is accurately measured.
The compound that this patent synthesized
Can be used for detecting nicotinic acid, work as compound
Do the time spent with nicotinic acid, solution becomes can bore hole observe orange red by colourless.
Claims (3)
1. has structural formula
Compound 9-fluorenes-
N '-(rhodamine 6G-hydrazides)
The described compound 9-of claim 1 fluorenes-
N 'The preparation method of-(rhodamine 6G-hydrazides) is characterized in that being undertaken by following step:
(1) preparation of rhodamine 6G hydrazides
Rhodamine 6G and 80% hydrazine hydrate are mixed in the ethanolic soln, and at room temperature stir, then mixture heating up is refluxed, when solution was become clarification orange by scarlet, reaction finished, and is cooled to room temperature, the vacuum rotary steam desolventizing, suction filtration obtains the light orange solid, and namely get crude product, wherein rhodamine 6G 2-3 time with the distilled water wash precipitation: the mol ratio of 80% hydrazine hydrate is 1: 1.5;
(2) target compound is synthetic
Round-bottomed flask is put in rhodamine 6G hydrazides and the Fluorenone mixing of above-mentioned preparation, add methanol solution, and add several glacial acetic acids as catalyzer, with mixed system reflux 5-6 hour, monitor with thin-layer chromatography, be down to room temperature after question response is finished, the mixed system in the flask is poured in the frozen water, use the triethylamine regulator solution to pH=8, suction filtration, and with distilled water wash precipitation 2-3 time, the thick product of gained separates through column chromatography, obtain structural formula and be the compound 9-fluorenes of I-
N '-(rhodamine 6G-hydrazides); Rhodamine 6G hydrazides and be 1.25: 1 to the mol ratio of Fluorenone wherein.
The described compound 9-of claim 1 fluorenes-
N '-(rhodamine 6G-hydrazides) preparing as the application aspect hydrogen ion highly selective bore hole colour developing identification and fluorescence identification probe.
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