CN104059005B - A kind of fluorescent molecular probe compound and its preparation method and application - Google Patents

A kind of fluorescent molecular probe compound and its preparation method and application Download PDF

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CN104059005B
CN104059005B CN201410263497.6A CN201410263497A CN104059005B CN 104059005 B CN104059005 B CN 104059005B CN 201410263497 A CN201410263497 A CN 201410263497A CN 104059005 B CN104059005 B CN 104059005B
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molecular probe
fluorescent molecular
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刘又年
臧启光
阮刻鸿
王立强
李娟�
邓留
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Central South University
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Abstract

The invention discloses a kind of fluorescent molecular probe compound and its preparation method and application, the preparation method of fluorescent molecular probe compound be first by the benzophenone derivative of halogen substituent at Zn/TiCl 4react under catalysis, reaction product and reactive magnesium generate Grignard reagent, then with CO 2reaction and acidifying, acidizing product carries out amidation with secondary amine after oxalyl chloride acidylate, more further with Lawesson ' s reagent react, namely the fluorescent molecular probe compound that stability is high, scale resistance is good is obtained, this preparation method is simple to operate, and raw material is easy to get, and reaction conditions is gentle; Obtained fluorescent molecular probe compound can be used for detecting the hypochlorite ion in the aqueous solution, and it is higher to have sensitivity, strong to hypochlorite recognition capability, and response speed is very fast, scope is wide, the feature that detectability is low; The fields such as water body detection, environmental monitoring can be widely used in.

Description

A kind of fluorescent molecular probe compound and its preparation method and application
Technical field
The present invention relates to a kind of fluorescent molecular probe compound and its preparation method and application, belong to chemical analysis detection technique field.
Background technology
Hypochlorite has very strong oxidisability, and be common oxygenant in industry and life, its representative species is clorox, chlorinated lime etc., is widely used in the oxygenant etc. in the bleaching of timber paper, apparatus and water body disinfection, organic synthesis.But hypochlorite has certain toxicity to environment and human body, improper use or a large amount of residual hypochlorite may cause the pollution of environment, such as: according to national standard, when tap water dispatches from the factory, its contents of residual chlorine should be no more than 0.3mg/L, and swimming pool contents of residual chlorine should be no more than 0.6mg/L [1]([1] " drinking water sanitary standard " (GB5749-2006)).Therefore, develop, to the monitoring method that accurately facilitates of hypochlorite ion's content, there is Great significance.
In traditional water sample, the detection by quantitative of hypochlorite ion generally adopts diaminoditolyl colorimetric to send out method, iodometric titrationiodimetry titration analysis etc.These methods are not high to some other common oxidizing substance selectivity in water body: as Fe 3+, NO 2 -, when Mn (IV) plasma coexists, comparatively big error can be caused.Meanwhile, the analytical procedure of volumetry is loaded down with trivial details, and preparation of reagents is complicated, analyzes medicine and the shortcoming such as can not to preserve for a long time and also limit its application.Comparatively speaking, small-molecule fluorescent probe is when detecting hypochlorite ion, and sample preparation is simple, and detection signal adopts the analysis of instrument accurate acquisition, convenient and swift [2-6]([2] Chem-Eur.J.2009,15,2305.Lin, W.Y.; Long, L.L.; Chen, B.B.; Tan, W.; [3] Chem.Comm.2011,47,11978.Cheng, X.H.; Jia, H.Z.; Long, T.; Feng, J.; [4] J.Am.Chem.Soc.2007,129,7313.Kenmoku, S.; Urano, Y.; Kojima, H.; Nagano, T.; [5] J.Am.Chem.Soc.2011,133,5680.Koide, Y.; Urano, Y.; Hanaoka, K; Terai, T.; [6] Chem.Comm.2011,47,4373.Chen, X.Q.; Lee, K.A.; Ha, E.M.; Seo, Y.Y.; Choi, H.K.).As everyone knows, hypochlorite ion has very strong oxidizing property, makes the probe molecule that it is easy in oxidizing solution, destroys its fluorescent characteristic.After the self-assembly in aqueous phase of this probe small molecules is colloidal particle, effectively can improve the tolerance of molecule to strong oxidizing property detection system.It is active that tetraphenyl ethylene group has aggregation inducing fluorescent emission (AIE) [7]([7] J.Org.Comm.2006,71,9873.Duan, X.F.; Zeng, J.; Lu, J.W.; Zhang, Z.B.).
Summary of the invention
An object of the present invention is to be to provide a kind of scale resistance good and have the fluorescent molecular probe compound of the active tetraphenyl ethylene fluorophor of aggregation inducing fluorescent emission (AIE).
Another object of the present invention is to provide the method that reaction conditions is gentle, simple to operate, low cost prepares described fluorescent molecular probe compound.
3rd object of the present invention be to provide described fluorescent molecular probe compound hypochlorite ion in solution fluoroscopic examination in application, this application has the features such as selectivity is good, highly sensitive, linearity range is wide.
The invention provides a kind of fluorescent molecular probe compound, this fluorescent molecular probe compound has structure shown in formula 1:
Wherein, R 1, R 2, R 3and R 4be selected from the one in group, H atom, methyl, ethyl and the methoxyl group with formula 2 structure independently of one another, and R 1, R 2, R 3and R 4in have at least one to be selected from the group with formula 2 structure; R 5and R 6be selected from the one in methyl, ethyl and propyl group independently of one another.
Preferred fluorescent molecular probe compound has structure shown in formula 3:
Present invention also offers the preparation method of shown fluorescent molecular probe compound, this preparation method will have the benzophenone derivative of formula 4 structure and formula 5 structure at Zn/TiCl 4react under catalysis, obtain 1,1,2, the 2-tetraphenyl ethylene derivative with formula 6 structure; After gained 1,1,2,2-tetraphenyl ethylene derivative and reactive magnesium generate Grignard reagent, then with CO 2reaction, reaction product is acidified, obtains 1,1,2,2-tetraphenyl ethylene benzoic acid derivative; Gained 1,1,2,2-tetraphenyl ethylene benzoic acid derivative after oxalyl chloride acidylate, then carries out amidate action with the secondary amine with formula 7 structure, obtains 1,1,2,2-tetraphenyl ethylene benzamide derivatives; Gained 1,1,2,2-tetraphenyl ethylene benzamide derivatives further with Lawesson ' s reagent react, obtain the fluorescent molecular probe compound with formula 1 structure;
Wherein, R 7, R 8, R 9and R 10be selected from the one in halogen atom, H atom, methyl, ethyl or methoxyl group independently of one another, R 7, R 8, R 9and R 10in have at least one to be selected from halogen atom.
The preparation method of fluorescent molecular probe compound of the present invention also comprises following preferred version:
Preferred halogen atom is bromine or chlorine atom; Most preferably be bromine atoms.
The benzophenone derivative in preferred preparation method with formula 4 structure and formula 5 structure refluxes 6 ~ 10h in tetrahydrofuran (THF).
1,1,2,2-tetraphenyl ethylene benzoic acid derivative described in preferred preparation method and oxalyl chloride first react 1 ~ 3h in ice bath, then in ice bath, react 0.5 ~ 1.5h with the secondary amine with formula 7 structure further.
1,1,2,2-tetraphenyl ethylene benzamide derivatives described in preferred preparation method and Lawesson ' s reagent are at reflux in toluene 3 ~ 7h.
Present invention also offers the application of shown fluorescent molecular probe compound, this application is the fluoroscopic examination shown fluorescent molecular probe compound being applied to hypochlorite ion in the aqueous solution.
Preferred application method, obtains probe colloid test fluid with a small amount of acetonitrile by joining after fluorescent molecular probe compound dissolution in PBS buffered soln, then detects after adding ion to be tested.
Hypochlorite ion described in preferred application method is the hypochlorite ion in hypochlorite.
Described hypochlorite comprises clorox, Losantin etc.
Described fluorescent molecular probe compound can be directly used in the detection of the hypochlorite ion in aqueous phase system, detects under being applicable to room temperature.
The synthetic route following (making an explanation with the example that synthesizes of the fluorescent molecular probe compound with formula 3 structure) of fluorescent molecular probe compound of the present invention:
Fluorescent molecular probe compound of the present invention builds tetraphenyl ethylene fluorescence skeleton by 4,4 '-disubstituted benzophenone derivates, and introduces thioamides radical moiety as recognition group.The mechanism of fluorescent molecular probe compound test hypochlorite ion of the present invention is (making an explanation for the fluorescent molecular probe compound with formula 3 structure): fluorescent molecular probe compound of the present invention is under hypochlorite strong oxidation, thioamides radical oxidation wherein becomes amide group, thus eliminate the heavy atoms effect of sulphur atom generation, the triplet state intersystem crossing of molecular-excited state is effectively suppressed, and its fluorescence emission spectrum strength of signal being positioned at wavelength about 490nm obviously strengthens;
Beneficial effect of the present invention:
The preparation method of fluorescent molecular probe compound of the present invention is simple to operate, and raw material is easy to get, and reaction conditions is gentle.
Fluorescent molecular probe compound chemistry stable in properties of the present invention, excellent optical performance is high to strong oxidizer tolerance degree.
Fluorescent molecular probe compound of the present invention self aggregation in aqueous phase is colloidal particle, effectively can improve the tolerance of probe to strong oxidizing property detection system, make the probe molecule aggregate of this colloidal state be applicable to realize quantitative analysis within the scope of the hypochlorite concentration of 3 ~ 500 μMs.Fluorescence probe compound of the present invention is colloidal state in aqueous, does not almost observe fluorescent signal.Along with adding of hypochlorite, in fluorescence spectrum, there is maximum emission peak at 490nm place in probe molecule, and along with the increase of hypochlorite concentration, its fluorescence intensity also increases thereupon, and maximum enhancing is 88 times; Under the ultra violet lamp of 365nm wavelength, the probe in detecting system after response presents stronger green-fluorescent emission.Fluorescent molecular probe compound of the present invention is applied to the hypochlorite ion detected in the aqueous solution, and sensitivity is higher, strong to hypochlorite recognition capability, and response speed is very fast, and responding range is 0 ~ 500 μM, and lowest detection is limited to 3.0 μMs; This fluorescent molecular probe compound has actual using value in fields such as water body detection, environmental monitorings.
Accompanying drawing explanation
[Fig. 1], for the obtained fluorescent probe of embodiment 1 is in PBS buffered soln (100mM, pH=7.0), is 490nm place fluorescence intensity change relation curve in time at wavelength after adding 500 μMs of clorox.
[Fig. 2] for the obtained fluorescent probe of embodiment 1 is in PBS buffered soln (100mM, pH=7.0), the change curve that fluorescence emission spectrum increases with hypochlorite concentration.
[Fig. 3] for the obtained fluorescent probe of embodiment 1 is in PBS buffered soln (100mM, pH=7.0), the linear relationship graphic representation of fluorescence intensity and hypochlorite concentration's (0 ~ 70 μM) after reaction.
[Fig. 4] for the obtained fluorescent probe of embodiment 1 is in PBS buffered soln (100mM, pH=7.0), the linear relationship graphic representation of fluorescence intensity and hypochlorite concentration's (200 ~ 500 μMs) after reaction.
[Fig. 5], for the obtained fluorescent probe of embodiment 1 is in PBS buffered soln (100mM, pH=7.0), fluorescence spectrum is with the different anions adding same concentration: ClO -, ClO 3 -, ClO 4 -, SO 3 2-, HSO 3 -, S 2o 3 2-, Cr 2o 7 2-, F -, Cl -, Br -, I -, CN -, S 2-, SO 4 2-, NO 3 -, NO 2 -, PO 4 3-, HPO 4 2-, CO 3 2-, HCO 3 -after change curve.
[Fig. 6], for the obtained fluorescent probe of embodiment 1 is in PBS buffered soln (100mM, pH=7.0), adds the different anions of 500 μMs: ClO -, ClO 3 -, ClO 4 -, SO 3 2-, HSO 3 -, S 2o 3 2-, Cr 2o 7 2-, F -, Cl -, Br -, I -, CN -, S 2-, SO 4 2-, NO 3 -, NO 2 -, PO 4 3-, HPO 4 2-, CO 3 2-, HCO 3 -rear fluorescence emission spectrum is in wavelength 490nm place fluorescence intensity histogram.
[Fig. 7] for the obtained fluorescent probe of embodiment 1 is in PBS buffered soln (100mM, pH=7.0), respectively at the different anions of 500 μMs: ClO 3 -, ClO 4 -, F -, Cl -, Br -, SO 4 2-, NO 3 -, PO 4 3-, HPO 4 2-, CO 3 2-, HCO 3 -when coexisting, containing 500 μMs of ClO -detection system in 490nm place fluorescence intensity histogram.
[Fig. 8] for probe that embodiment 1 is obtained under different pH conditions, add the clorox of 500 μMs after the change curve of fluorescence intensity.
The proton nmr spectra of the fluorescence probe of the synthesis that [Fig. 9] obtains for embodiment 1.
The proton nmr spectra of 1,2-bis-(the bromo-phenyl of 4-)-1,2-diphenylethlene that [Figure 10] obtains for embodiment 1.
The proton nmr spectra of 1,2-bis-(4-carboxyl phenyl)-1,2-diphenylethlene that [Figure 11] obtains for embodiment 1.
The proton nmr spectra of 1,2-bis-(4-N, N-diethyl-benzamide) base-1,2-diphenylethlene that [Figure 12] obtains for embodiment 1.
Embodiment
Following examples are intended to further illustrate content of the present invention, instead of limit the scope of the invention.
Embodiment 1
The preparation of 1,2-bis-(the bromo-phenyl of 4-)-1,2-diphenylethlene:
Bromo-for 4-benzophenone (8.0g, 30.8mmol), Zn powder (7.8g, 120mmol) are added in 250mL anhydrous tetrahydro furan, drips titanium tetrachloride (6mL, 53mmol) under ice bath, then reflux 8h.Monitor reaction process with thin-layer chromatography, treat that raw material reaction is complete, cool to room temperature, distillation is except desolventizing.Use dichloromethane extraction again, organic phase uses saturated aqueous common salt and water washing respectively.Be separated organic phase, add anhydrous sodium sulfate drying, distillation is except desolventizing, and (developping agent is sherwood oil to column chromatographic isolation and purification, R f=0.6) pure white solid 1,2-bis-(the bromo-phenyl of 4-)-1,2-diphenylethlene is obtained, output 5.21g, productive rate 69.4%.
H 1NMR(400MHz,CDCl 3):δ ppm＝7.30(1H,s),7.28(1H,s),7.26(1H,s),7.24(1H,s),7.19-7.15(3H,m),7.15-7.11(3H,dd,J＝3.2Hz),7.09-6.98(4H,m),6.96-6.87(3H,tt,J＝8.8Hz,2.0Hz).
The preparation of 1,2-bis-(4-carboxyl phenyl)-1,2-diphenylethlene:
Take 1,2-bis-(the bromo-phenyl of 4-)-1,2-diphenylethlene 2.0g, be dissolved in 20mL anhydrous tetrahydro furan, obtain A liquid.Take 0.5g through dilute hydrochloric acid washing and dried magnesium chips in 100mL three-necked bottle, N 2add 10mL anhydrous tetrahydro furan under protection, stir lower dropping 0.5mL methyl iodide, be heated to initiation reaction of seething with excitement, under keeping slight boiling condition with post-heating, the A liquid that slow dropping has been prepared, dropwises rear backflow 2h, subsequently in N 2be cooled to room temperature under protection, in reaction system, pass into excessive dry CO 2gas (5L), elimination magnesium chips, drips dilute hydrochloric acid and regulates pH<5.0, with dichloromethane extraction, isolate organic layer, use saturated aqueous common salt respectively, deionized water wash, anhydrous sodium sulfate drying.Distillation is except after desolventizing, and column chromatographic isolation and purification (developping agent is the methylene dichloride of volume ratio 10:1: methyl alcohol) obtains faint yellow solid 1,2-bis-(4-carboxyl phenyl)-1,2-diphenylethlene, output 0.075g, productive rate 4.4%.
H 1NMR(400MHz,DMSO-D6):δ ppm＝12.90(2H,s),7.22-6.93(18H,m).
The preparation of 1,2-bis-(4-N, N-diethyl-benzamide) base-1,2-diphenylethlene:
1,2-bis-(4-carboxyl phenyl)-1,2-diphenylethlene (75mg, 0.18mmol) is dissolved in 3mL anhydrous tetrahydro furan, drips oxalyl chloride under ice bath and generate (about 0.5mL) to without gas, room temperature reaction 2h.Ice bath again subsequently, drips diethylamine 3mL, after room temperature reaction 1h, by system liquid impouring deionized water, with dichloromethane extraction product, isolate organic layer, use dilute hydrochloric acid (5%v/v) respectively, saturated aqueous common salt, deionized water wash, anhydrous sodium sulfate drying.After distillation removes desolventizing, column chromatographic isolation and purification (methylene dichloride: sherwood oil=2:5v/v is developping agent, Rf=0.6), obtain yellow solid 1,2-bis-(4-N, N-diethyl-benzamide) base-1,2-diphenylethlene, output 79mg, productive rate 83%.
H 1NMR(400MHz,CDCl 3):δ ppm＝7.55-6.85(18H,m),3.73-3.37(4H,m),3.35-2.95(4H,m),1.38-1.12(12H,m).
The preparation of probe molecule:
By 1,2-bis-(4-N, N-diethyl-benzamide) base-1,2-diphenylethlene (79mg, 0.15mmol) and lawesson reagent (133mg, 0.33mmol) in 10mL reflux in toluene reaction 5h, thin-layer chromatography detection reaction carries out degree, after question response, revolves and steams except desolventizing, crude product column chromatographic isolation and purification (methylene dichloride developping agent, R f=0.9), pure target compound 1,2-bis-(4-N, N-diethyl thiobenzamide) base-1,2-diphenylethlene is obtained, output 38mg, productive rate 45%.
H 1NMR(400MHz,CDCl 3):δ ppm＝7.25-6.85(18H,m),4.10(4H,dd,J＝7.1Hz),3.38(4H,dd,J＝7.1Hz),1.37(6H,t,J＝6.7Hz),1.10(6H,t,J＝7.0Hz).
Embodiment 2
Fluorescence Increasing detects the application of hypochlorite fluorescent probe:
This fluorescent probe is dissolved in acetonitrile, obtains probe solution (0.02mol/L), join subsequently in PBS buffered soln (100mM, pH=7.0), shake up, obtain probe test liquid.Add corresponding test ion, system is made into containing probe molecule 5 μMs, probe colloidal solution containing different concns test ion, tests the change of its fluorescence spectrum.Fig. 1-Fig. 8 shows, probe has very high selectivity to hypochlorite ion, along with its fluorescence spectrum generation considerable change of increase of hypochlorite ion's concentration, after adding hypochlorite ion, fluorescence intensity strengthens 88 times, and probe is not by the impact of other Common Anions, as: ClO 3 -, ClO 4 -, F -, Cl -, Br -, SO 4 2-, NO 3 -, PO 4 3-, HPO 4 2-, CO 3 2-, HCO 3 -.Under above-mentioned interfering ion existent condition, probe still has good selectivity and sensitivity to hypochlorite ion.

Claims (10)

1. a fluorescent molecular probe compound, is characterized in that, has structure shown in formula 1:
Wherein, R 1, R 2, R 3and R 4be selected from the one in group, H atom, methyl, ethyl and the methoxyl group with formula 2 structure independently of one another, R 1and R 2in have at least one to be selected from the group with formula 2 structure, and R 3and R 4in have at least one to be selected from the group with formula 2 structure; R 5and R 6be selected from the one in methyl, ethyl and propyl group independently of one another.
2. fluorescent molecular probe compound as claimed in claim 1, is characterized in that having structure shown in formula 3:
3. the preparation method of the fluorescent molecular probe compound shown in claim 1 or 2, is characterized in that, has the benzophenone derivative of formula 4 structure and formula 5 structure at Zn/TiCl 4react under catalysis, obtain 1,1,2, the 2-tetraphenyl ethylene derivative with formula 6 structure; After gained 1,1,2,2-tetraphenyl ethylene derivative and reactive magnesium generate Grignard reagent, then with CO 2reaction, reaction product is acidified, obtains 1,1,2,2-tetraphenyl ethylene benzoic acid derivative; Gained 1,1,2,2-tetraphenyl ethylene benzoic acid derivative after oxalyl chloride acidylate, then carries out amidate action with the secondary amine with formula 7 structure, obtains 1,1,2,2-tetraphenyl ethylene benzamide derivatives; Gained 1,1,2,2-tetraphenyl ethylene benzamide derivatives further with Lawesson ' s reagent react, obtain the fluorescent molecular probe compound with formula 1 structure;
Wherein, R 7and R 8in have at least one to be selected from halogen atom, and R 9and R 10in have at least one to be selected from halogen atom.
4. preparation method as claimed in claim 3, it is characterized in that, described halogen atom is bromine atoms.
5. preparation method as claimed in claim 3, is characterized in that, the benzophenone derivative with formula 4 structure and formula 5 structure refluxes 6 ~ 10h in tetrahydrofuran (THF).
6. preparation method as claimed in claim 3, is characterized in that, 1,1,2,2-described tetraphenyl ethylene benzoic acid derivative and oxalyl chloride first react 1 ~ 3h in ice bath, then in ice bath, react 0.5 ~ 1.5h with the secondary amine with formula 7 structure further.
7. preparation method as claimed in claim 3, it is characterized in that, 1,1,2,2-described tetraphenyl ethylene benzamide derivatives and Lawesson ' s reagent are at reflux in toluene 3 ~ 7h.
8. the application of the fluorescent molecular probe compound shown in claim 1 or 2, is characterized in that, is applied to the fluoroscopic examination of hypochlorite ion in the aqueous solution.
9. apply as claimed in claim 8, it is characterized in that, obtain probe colloid test fluid with a small amount of acetonitrile by joining after fluorescent molecular probe compound dissolution in PBS buffered soln, then detect after adding ion to be tested.
10. apply as claimed in claim 8, it is characterized in that, described hypochlorite ion is the hypochlorite ion in hypochlorite.
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