CN108219772A - Imidazoles [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe and its application - Google Patents

Imidazoles [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe and its application Download PDF

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CN108219772A
CN108219772A CN201611202842.0A CN201611202842A CN108219772A CN 108219772 A CN108219772 A CN 108219772A CN 201611202842 A CN201611202842 A CN 201611202842A CN 108219772 A CN108219772 A CN 108219772A
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imidazoles
pyridine
formula
ratio
fluorescent probe
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葛燕青
邢旭娇
曹晓群
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Taishan Medical University
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Abstract

The invention discloses a kind of imidazoles [1,5 a] and pyridine derived species Hg2+Ratio fluorescent probe, the probe be imidazoles [1,5 a] and pyridine modification rhodamine, chemical structural formula such as formula（1）It is shown.The fluorescence probe of the present invention is in ethanol/water（Volume ratio 1:4）To Hg in solution2+There are unique fluorescence selectivity, higher sensitivity and stronger anti-other ion interference abilities, there is huge application prospect.

Description

Imidazoles [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe and its application
Technical field
The present invention relates to organic molecule fluorescence probe field more particularly to a kind of imidazoles [1,5-a] and pyridine derivates Class Hg2+Ratio fluorescent probe and its application.
Background technology
In industry and life, there is a large amount of mercury to be discharged into environment daily.Even if very small amount, mercury for Environment, the mankind are also very harmful.Mercury can be accumulated and not biodegradable in human body, so as to cause health problem, Such as the diseases such as renal damage, cell dysfunction, neurological disorders.Therefore, the qualitative and quantitative detection of mercury ion is become in recent years Come the field that chemists are paid special attention to.
At present, many analysis methods are used to mercury ion in detection environment, such as atomic absorption spectrum, electrochemical method, electricity Feel coupled plasma-atomic emission spectrometry and mass spectrum etc..But these analysis methods require have special instrument and equipment and Complicated flow and operation etc..
For the method for fluorescence probe detection metal ion because cheap, high sensitivity, molecular structure is easy to modification optimization, surveys Examination polyvinyl chloride facilitates, and causes the very big interest of chemist.At present, have largely about mercury ion fluorescence probe Document report.However, most of mercury ion probes are single signal enhancing or attenuated type probe, this kind of probe is often by perhaps The interference of more extraneous factors（Such as temperature, concentration and probe concentration, instrument slit, photobleaching）And there is the testing result of false positive.Than Rate fluorescence probe is used as signal output by the ratio of the fluorescence intensity at different wave length and reaches detection object analyte Purpose, it can be good at solving the above problems.Fluorescence resonance energy transfer（FRET）It is that currently used one kind is highly effective Designed ratios probe method.But the dyestuff that can be used in building FRET systems at present is also seldom, and based on fluorescence resonance energy The ratio fluorescent probe that amount principle of transfer is used to detect mercury ion is less.Therefore, develop novel fluorescence dyestuff, for build mercury from Sub- ratio fluorescent probe is one and significantly works.
Invention content
In view of the deficiencies of the prior art, the present invention solves the problems, such as to be to provide a kind of imidazoles of two signals response variation [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe and its application.
The technical scheme is that：A kind of imidazoles [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe is changed Learn structural formula such as formula（1）It is shown：
The invention also includes imidazoles [1,5-a] and pyridine derived species Hg2+The application of ratio fluorescent probe, formula（1）Compound exists In ethanol/water solution（Volume ratio 1:4）To Hg2+There is unique fluorescence selectivity.
The invention also includes imidazoles [1,5-a] and pyridine derived species Hg2+The synthetic method of ratio fluorescent probe, in N, N- In dimethyl formamide solution, by imidazoles [1,5-a] and pyridine rhodamine hydrazides and phenyl isothiocyanate are according to 1:5 rate of charges , it is reacted 10 hours under room temperature, obtains imidazoles [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe.
Prepare imidazoles [1,5-a] and pyridine derived species Hg2+The acetonitrile/water of ratio fluorescent probe（Volume ratio 1:4）Solution, It is separately added into quantitative LiCl, NaCl, KCl, MgCl2·6H2O, CaCl2·6H2O, AlCl3·6H2O, Pb（NO3）2, CrCl3·6H2O, MnCl2·4H2O, FeCl3·6H2O, FeCl2·4H2O, CoCl2·6H2O, NiCl2·6H2O, HgCl2, C4H6O4Zn·2H2O,SrCl2·6H2O CuCl2·2H2O, CdCl2·2½H2O, AgNO3Aqueous solution, by glimmering Light spectrum test studies the selectivity to different metal ions, surveys the discovery of its fluorescence emission spectrum Strength Changes：Institute of the present invention State imidazoles [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe, that is, formula（1）Compound is to Hg2+There is unique fluorescence to select Property, as shown in Figure 1.It is gradually added into Hg2+To 1 equivalent, the fluorescence intensity at 466nm of compound 1 is substantially reduced, meanwhile, Fluorescence intensity is remarkably reinforced at 584nm, as shown in Figure 2.Therefore, imidazoles [1,5-a] and pyridine derivate, that is, formula（1）Compound is made For Hg2+Ratio fluorescent probe has huge application.
The present invention provides a kind of imidazoles [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe, that is, formula（1）Chemical combination Object, experiment prove formula of the present invention（1）Compound can be with Hg2+In ethanol/water（Volume ratio 1:4）With stoichiometric ratio in solution 1:1 reaction, during the reaction, since rhodamine and mercury ion act on, hydrolysis, so as to make donor imidazoles [1,5-a] simultaneously With receptor rhodamine energy transmission occurs for pyridine, and the fluorescence intensity at 466nm of compound 1 is caused to be substantially reduced, meanwhile, Fluorescence intensity is remarkably reinforced at 584nm.Thus susceptible of proof formula of the present invention（1）Compound is in ethanol/water（Volume ratio 1:4）It is molten To Hg in liquid2+There are unique fluorescence selectivity, higher sensitivity and stronger anti-other ion interference abilities, have huge Application prospect.
Description of the drawings
Fig. 1：Formula（1）Compound（10-6M）Ethanol/water（Volume ratio 1:4）In solution add in equivalent different metal from Fluorescence intensity change ratio bar graphs after son, ordinate is the ratio between light intensity at the light intensity and 466nm at 584nm places in Fig. 1.
Fig. 2：Formula（1）Compound（10-6M）Ethanol/water（Volume ratio 1:4）Hg is carried out in solution2+Fluorescence titration figure.Figure Middle FL Intensity are fluorescence intensity, and Wavelength is wavelength, and equiv is multiple.
Fig. 3：Formula（1）Compound（10-6M）With the Hg of equivalent2+The ethanol/water coexisted（Volume ratio 1:4）It is added in solution The variation block diagram of fluorescence intensity ratio after other metal ions of equivalent.
Fig. 4 is formula（1）Compound synthesis method reaction equation figure.
Specific embodiment
Embodiment 1：Formula（1）The synthetic schemes of compound is shown below：
Specific synthesis step is as follows：
0.141g is sequentially added in 50 mL round-bottomed flasks（2.0 mmol）Imidazoles [1,5-a] and pyridine rhodamine hydrazides, 0.135g（10 mmol）Phenyl isothiocyanate, 20 mL n,N-Dimethylformamide are reacted 10 hours under room temperature.TLC detections are anti- After the completion of answering, 100 mL dichloromethane are added in, 30 mL are washed three times, the drying of dichloromethane layer sodium sulphate, concentration, and column chromatography obtains 0.126g aubergine solids, yield 75%.
Nuclear magnetic resonance hydrogen spectruming determining：1H NMR（400 MHz, CDCl3）：δ8.04 (d, J = 8.0 Hz,1H), 7.74- 7.60 (m, 3H), 7.50 (d, J = 4.0 Hz, 2H), 7.28 (s, 1H), 7.20 (m, 2H), 7.11 (m, 1H), 7.06 (d, J = 8.0 Hz, 2H), 6.92 (s, 1H), 6.69 (m, 2H), 6.53 (s, 3H), 6.45 (s, 1H), 6.32 (d, J = 8.0 Hz, 1H), 3.81 (s, 4H), 3.35 (q, J = 8.0 Hz, 4H), 3.27 (s, 4H), 2.96 (t, J = 8.0 Hz, 2H),1.82 (m, 2H), 1.65 (s, 2H), 1.43 (m, 2H), 2.57 (s, 3H), 1.16 (t, J = 8.0 Hz, 6H), 0.96 (t, J = 8.0 Hz, 3H)。13C NMR （100 MHz, CDCl3）：δ182.4, 168.3, 167.0, 154.0, 153.9, 152.1, 149.6, 138.5, 134.5, 129.4, 128.3, 127.8, 126.1, 124.8, 124.7, 124.4, 124.1, 123.7, 120.8, 117.5, 112.4, 103.4, 66.8, 48.4, 29.0, 26.3, 22.5, 13.8, 12.4。
Embodiment 2：
To formula（1）Compound（10-6M）Ethanol/water（Volume ratio 1:4）The Hg of 1 equivalent is separately added into solution2+, Ag+, Al3 +, Ca2+, Cd2+, Co2+, Cr3+, Cu2+, Fe2+, Fe3+, K+, Li+, Mg2+, Mn2+, Na+, Ni2+, Pb2+, Sr2+ And Zn2+Afterwards, it surveys it and changes discovery in 466nm and 584nm fluorescent emission intensities ratio：Formula（1）Compound is to Hg2+There is uniqueness Fluorescence selectivity, add in 1 equivalent Hg2+Afterwards, the fluorescence intensity at 466nm of compound 1 is substantially reduced, meanwhile, at 584nm Fluorescence intensity is remarkably reinforced, I584/I466 =3.3, as shown in Figure 2.
Embodiment 3：
In formula（1）Compound（10-6M）With the Hg of 1 equivalent2+Ethanol/water（Volume ratio 1:4）1 equivalent is separately added into solution Hg2+, Ag+, Al3+, Ca2+, Cd2+, Co2+, Cr3+, Cu2+, Fe2+, Fe3+, K+, Li+, Mg2+, Mn2+, Na+, Ni2 +, Pb2+, Sr2+And Zn2+Afterwards, it surveys it and changes discovery in 466nm and 584nm fluorescent emission intensities ratio：Formula（1）Compound There is stronger antijamming capability to other ions, as shown in Figure 3.
0.141g is sequentially added in 50 mL round-bottomed flasks（2.0 mmol）Imidazoles [1,5-a] and pyridine rhodamine hydrazides, 0.135g（10 mmol）Phenyl isothiocyanate, 20 mL n,N-Dimethylformamide are reacted 10 hours under room temperature.TLC detections are anti- After the completion of answering, 100 mL dichloromethane are added in, 30 mL are washed three times, the drying of dichloromethane layer sodium sulphate, concentration, and column chromatography obtains 0.126g aubergine solids, yield 75%.
Nuclear magnetic resonance hydrogen spectruming determining：1H NMR（400 MHz, CDCl3）：δ8.04 (d,J = 8.0 Hz,1H), 7.74- 7.60 (m, 3H), 7.50 (d, J = 4.0 Hz, 2H), 7.28 (s, 1H), 7.20 (m, 2H), 7.11 (m, 1H), 7.06 (d, J = 8.0 Hz, 2H), 6.92 (s, 1H), 6.69 (m, 2H), 6.53 (s, 3H), 6.45 (s, 1H), 6.32 (d, J = 8.0 Hz, 1H), 3.81 (s, 4H), 3.35 (q, J = 8.0 Hz, 4H), 3.27 (s, 4H), 2.96 (t, J = 8.0 Hz, 2H),1.82 (m, 2H), 1.65 (s, 2H), 1.43 (m, 2H), 2.57 (s, 3H), 1.16 (t, J = 8.0 Hz, 6H), 0.96 (t, J = 8.0 Hz, 3H)。13C NMR （100 MHz, CDCl3）：δ182.4, 168.3, 167.0, 154.0, 153.9, 152.1, 149.6, 138.5, 134.5, 129.4, 128.3, 127.8, 126.1, 124.8, 124.7, 124.4, 124.1, 123.7, 120.8, 117.5, 112.4, 103.4, 66.8, 48.4, 29.0, 26.3, 22.5, 13.8, 12.4。
Embodiment 2：
To formula（1）Compound（10-6M）Ethanol/water（Volume ratio 1:4）The Hg of 1 equivalent is separately added into solution2+, Ag+, Al3 +, Ca2+, Cd2+, Co2+, Cr3+, Cu2+, Fe2+, Fe3+, K+, Li+, Mg2+, Mn2+, Na+, Ni2+, Pb2+, Sr2+ And Zn2+Afterwards, it surveys it and changes discovery in 466nm and 584nm fluorescent emission intensities ratio：Formula（1）Compound is to Hg2+There is uniqueness Fluorescence selectivity, add in 1 equivalent Hg2+Afterwards, the fluorescence intensity at 466nm of compound 1 is substantially reduced, meanwhile, at 584nm Fluorescence intensity is remarkably reinforced, I584/I466 =3.3, as shown in Figure 2.
Embodiment 3：
In formula（1）Compound（10-6M）With the Hg of 1 equivalent2+Ethanol/water（Volume ratio 1:4）1 equivalent is separately added into solution Hg2+, Ag+, Al3+, Ca2+, Cd2+, Co2+, Cr3+, Cu2+, Fe2+, Fe3+, K+, Li+, Mg2+, Mn2+, Na+, Ni2 +, Pb2+, Sr2+And Zn2+Afterwards, it surveys it and changes discovery in 466nm and 584nm fluorescent emission intensities ratio：Formula（1）Compound There is stronger antijamming capability to other ions, as shown in Figure 3.
To formula（1）Compound（10-6M）Ethanol/water（Volume ratio 1:4）The Hg of 1 equivalent is separately added into solution2+, Ag+, Al3+, Ca2+, Cd2+, Co2+, Cr3+, Cu2+, Fe2+, Fe3+, K+, Li+, Mg2+, Mn2+, Na+, Ni2+, Pb2+, Sr2+And Zn2+Afterwards, it surveys it and changes discovery in 466nm and 584nm fluorescent emission intensities ratio：Formula（1）Compound is to Hg2+Have Unique fluorescence selectivity adds in the Hg of 1 equivalent2+Afterwards, the fluorescence intensity at 466nm of compound 1 is substantially reduced, meanwhile, Fluorescence intensity is remarkably reinforced at 584nm, I584/I466 =3.3, as shown in Figure 2.
Embodiment 3：
In formula（1）Compound（10-6M）With the Hg of 1 equivalent2+Ethanol/water（Volume ratio 1:4）1 equivalent is separately added into solution Hg2+, Ag+, Al3+, Ca2+, Cd2+, Co2+, Cr3+, Cu2+, Fe2+, Fe3+, K+, Li+, Mg2+, Mn2+, Na+, Ni2 +, Pb2+, Sr2+And Zn2+Afterwards, it surveys it and changes discovery in 466nm and 584nm fluorescent emission intensities ratio：Formula（1）Compound There is stronger antijamming capability to other ions, as shown in Figure 3.

Claims (2)

1. a kind of imidazoles [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe, it is characterised in that：It is imidazoles [1,5-a] And the rhodamine of pyridine modification, chemical structural formula such as formula（1）It is shown：
Formula（1）Compound is in ethanol/water solution（Volume ratio 1:4）To Hg2+There is unique fluorescence selectivity.
2. imidazoles described in claim 1 [1,5-a] and pyridine derived species Hg2+The synthetic method of ratio fluorescent probe, feature It is：In n,N-Dimethylformamide, by imidazoles [1,5-a] and pyridine rhodamine hydrazides and phenyl isothiocyanate are according to 1:5 Ingredient proportion reacts 10 hours under room temperature, obtains imidazoles [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe.
CN201611202842.0A 2016-12-23 2016-12-23 Imidazoles [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe and its application Pending CN108219772A (en)

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CN108892681A (en) * 2018-09-12 2018-11-27 泰山医学院 A kind of imidazo [1,2-a] pyridines mercury ion Ratiometric fluorescent probe and its application
CN109370573A (en) * 2018-12-07 2019-02-22 江汉大学 A kind of fluorescence probe, the preparation method and applications of dimercurion and temperature detection
CN111024657A (en) * 2019-11-20 2020-04-17 南昌大学 Rapid detection of Hg in tea oil2+In a fluorescence method

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CN105885828A (en) * 2016-04-21 2016-08-24 湘潭大学 Method for preparing water-soluble mercury ion fluorescence probe on basis of rhodamine and application of water-soluble mercury ion fluorescence probe
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Publication number Priority date Publication date Assignee Title
CN108892681A (en) * 2018-09-12 2018-11-27 泰山医学院 A kind of imidazo [1,2-a] pyridines mercury ion Ratiometric fluorescent probe and its application
CN109370573A (en) * 2018-12-07 2019-02-22 江汉大学 A kind of fluorescence probe, the preparation method and applications of dimercurion and temperature detection
CN109370573B (en) * 2018-12-07 2021-05-18 江汉大学 Fluorescent probe for detecting bivalent mercury ions and temperature, preparation method and application thereof
CN111024657A (en) * 2019-11-20 2020-04-17 南昌大学 Rapid detection of Hg in tea oil2+In a fluorescence method

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