CN106008389A - Cu<2+> fluorescent probe based on benzoxazole structure and preparation method thereof - Google Patents

Cu<2+> fluorescent probe based on benzoxazole structure and preparation method thereof Download PDF

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CN106008389A
CN106008389A CN201610377277.5A CN201610377277A CN106008389A CN 106008389 A CN106008389 A CN 106008389A CN 201610377277 A CN201610377277 A CN 201610377277A CN 106008389 A CN106008389 A CN 106008389A
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fluorescent probe
benzoxazoles
preparation
dissolved
fluorescence
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田林
庄文昌
周颖梅
盛风涛
李昭
李靖
顾越飞
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Xuzhou University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • 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
    • G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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    • 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
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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    • 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

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Abstract

Belonging to the field of analytical chemistry, the invention discloses a Cu<2+> fluorescent probe based on benzoxazole structure and a preparation method thereof. The molecular formula of the Cu<2+> fluorescent probe is C21H24N4O3, and the structural formula of the probe is shown as the specification. The preparation method of the fluorescent probe consists of: preparation of 2-(2'-aminophenyl)benzoxazole, preparation of an intermediate, and preparation of a final product. According to the Cu<2+> fluorescent probe based on the benzoxazole structure and the preparation method thereof provided by the invention, the Cu<2+> fluorescent probe has good selectivity to Cu<2+> in water, wide linearity range, and very strong anti-interference ability, thus being an ideal Cu<2+> sensor.

Description

A kind of Cu based on benzoxazoles structure2+Fluorescent probe and preparation method thereof
Technical field
The present invention relates to analytical chemistry field, particularly relate to a kind of based on benzoxazoles structure Cu2+Fluorescent probe and preparation method thereof.
Background technology
Copper is also to be the life cycle requisite trace of Middle nutrition substance metabolism process in human body Element, simultaneously because the extensive application in a lot of industries, copper is also that a kind of important metal is dirty Dye thing, when the concentration of copper ion is relatively low, it is a kind of nutrient substance for various organs, but It is that people is known from experience generation toxicity by the existence of copper ion of excess, also can upset Normocellular simultaneously Function.Therefore, copper ion balance in vivo is relevant such as with many major diseases: Menkes Family name harvests a mao syndrome, Parkinson's disease, Wilson's disease, prions, senile dementia etc.. World Health Organization (WHO) specifies that the concentration of daily copper in drinking water ion not can exceed that 2ppm. is due to copper Ion has important effect and the impact on environment on biology.So developing single-minded selection Property, high sensitivity, low detection limit, range of linearity width, the water solublity Cu of strong interference immunity2+Pass Environmental science and life sciences are had great significance by sensor.
Many traditional qualitative-and-quantitative methods are used in the different copper ions in sample of analysis detection Content, such as utilize inductive coupling plasma mass spectrometry, atomic emission spectrum, atomic absorption light The large-scale precision instruments such as spectrum.But these methods are required for the instrument of costliness, at loaded down with trivial details sample Reason process and professional operator.These methods can not realize real-time in-situ inspection simultaneously Survey.Therefore, optical probe, particularly fluorescent probe, compared with other analysis methods, have Easily operated, analysis time is short, it is not necessary to complicated instrument, so being developing progressively in human body With the strong instrument detecting metal copper ion in water environment.
Current substantial amounts of compound is designed the existence synthesized for detecting copper ion, but, this A little probes mostly have the disadvantage that: the big portion of the synthetic method loaded down with trivial details (2) of (1) copper ion probe The monitoring divided is all to carry out seldom carrying out (3) in pure water solution in organic solution to resist Interference performance is poor, is particularly susceptible to Hg2+, Zn2+, Co2+,Cr3+The interference of ion.Above-mentioned this The application of fluorescent probe of a little drawbacks limit.
Summary of the invention
The technical problem to be solved in the present invention is, for Cu in prior art2+Detection fluorescence is visited Pin need to participate in organic solvent and selectivity is bad, the shortcoming that capacity of resisting disturbance is the strongest, it is provided that One can be good at Selective recognition copper ion in aqueous, and capacity of resisting disturbance is extremely strong, Range of linearity width, the Cu based on benzoxazoles structure that detection limit is low2+Fluorescent probe and preparation thereof Method.
The technical solution adopted for the present invention to solve the technical problems is as follows:
A kind of Cu based on benzoxazoles structure in the present invention2+Fluorescent probe, its structural formula such as formula Shown in I:
A kind of Cu based on benzoxazoles structure in the present invention2+The preparation method of fluorescent probe, its Synthetic route is as follows:
Further, described preparation method specifically includes following processing step:
Step A, join in polyphosphoric acids after ortho-aminobenzoic acid and the mixing of adjacent phenalgin phenol, React some hours at a certain temperature；
Step B, above-mentioned reactant liquor is cooled to uniform temperature after, reactant liquor is poured into water, Precipitation is collected by filtration, after a small amount of water washing precipitation, precipitation is dissolved in alkaline solution, filters, Precipitation washes with water, is then dried, and ethyl alcohol recrystallization obtains 2-(2 '-aminophenyl) benzo and dislikes Azoles sterling；
Step C, 2-(2 '-aminophenyl) benzoxazoles and DMAP are dissolved in dichloromethane；
Step D, that the chloro-acetyl chloride being dissolved in dichloromethane is added dropwise to above-mentioned mixing is molten In liquid, after stirring a period of time, rotation is steamed, and mixture uses column chromatography purification, obtains intermediate Sterling；
Step E, N-hydroxyethyl piperazine and intermediate are mixed after be dissolved in DMF, in stirring Under be slowly added to a certain amount of Anhydrous potassium carbonate after under uniform temperature, react some hours after；
Step F, being cooled to room temperature, be filtrated to get precipitation, filtrate is extracted with ethyl acetate, and closes And organic facies, it being dried, filter, column chromatography for separation obtains end product.
Preferably, described step A actual conditions is, ortho-aminobenzoic acid and adjacent phenalgin phenol mixing Rear grinding is uniform, joins, by grinding uniform mixture, the poly that quality is 20 times of mixture In phosphoric acid, then reacting at 220 DEG C under mechanical agitation, the response time is 3h.
Preferably, described step B actual conditions is, the temperature of cooling more than 60 DEG C, institute State reactant liquor to pour in boiling water, and 5 times that the volume of boiling water is polyphosphoric acids volume, described alkali Property solution be saturated sodium bicarbonate solution, described saturated sodium bicarbonate solution consumption be by solution adjust Solution is between pH8-9, and described being dried is carried out under vacuum.
Preferably, described step C actual conditions is, described 2-(2 '-aminophenyl) benzo Oxazole and DMAP are dissolved in dry dichloromethane.
Preferably, described step D actual conditions is, under argon shield, will be dissolved in dry two Chloro-acetyl chloride in chloromethanes is added dropwise in above-mentioned mixed solution, stirs 2h, and rotation is steamed, Mixture uses column chromatography purification, and during purification, eluant is petroleum ether/dichloromethane=2:1, V:V。
Preferably, described step E actual conditions is, described DMF carries out Non-aqueous processing before using, A length of 10h during described reaction.
Preferably, described step F actual conditions is, the described ethyl acetate extraction time-division three is inferior Volume extract, described dry time desiccant select anhydrous magnesium sulfate be dried, wash during column chromatography for separation De-agent is petrol ether/ethyl acetate=1:1, V:V.
A kind of Cu based on benzoxazoles structure in the present invention2+Fluorescent probe passes at copper ion chemistry The application in sensor field, described Cu2+Fluorescent probe can be used for copper ion in water environment and human body and contains The sensing detection of amount, described sensing detection is fluorescence intensity detection.
The beneficial effects of the present invention is, the invention provides a kind of based on benzoxazoles structure Cu2+Fluorescent probe, the Cu that the present invention provides2+Fluorescent probe can in biological cell, environment Cu in water body2+Detect.
The present invention provides that a kind of molecular structure is simple, synthetic method is simple, productivity is high, to copper from Son has preferable selectivity, extremely strong capacity of resisting disturbance, and the excellent range of linearity and low The Cu of detection limit2+Fluorescent probe.
Accompanying drawing explanation
The hydrogen spectrum confirming copper ion chemical sensor architecture and carbon that Fig. 1 provides for the present invention are composed；
The copper ion fluorescence probe compound that Fig. 2 provides for the present invention is to different metal ions Fluorescence intensity collection of illustrative plates；
The fluorescence intensity of the copper ion fluorescence probe compound that Fig. 3 provides for the present invention and copper from The titration curve of son；
The fluorescent probe of the copper ion fluorescence probe compound that Fig. 4 provides for the present invention and copper from The concentration range of linearity of son；
The copper ion chemical sensor that Fig. 5-1 provides for the present invention shows with copper ion reactive hydrogen spectrum It is intended to；
The copper ion chemical sensor that Fig. 5-2 provides for the present invention reacts cognitron with copper ion Reason schematic diagram；
The fluorescence intensity of the copper ion chemical sensor that Fig. 6 provides for the present invention and copper ion with Fluorescence intensity comparison diagram when other ions coexist；
Detailed description of the invention
The technology of the present invention below in conjunction with the accompanying drawings and is further illustrated by detailed description of the invention Scheme.
A kind of Cu based on benzoxazoles structure in this example2+Fluorescent probe, its molecular structural formula As follows:
A kind of Cu based on benzoxazoles structure in this example2+The preparation method of fluorescent probe, its Synthetic route is as follows:
In this example, described preparation method specifically includes following processing step:
Step A, ortho-aminobenzoic acid and o-aminophenol are mixed after grind uniformly, will grind Uniform mixture joins in the polyphosphoric acids that quality is 20 times of mixture, then in machinery Reacting at 220 DEG C under stirring, the response time is 3h；
Step B, above-mentioned reactant liquor is cooled to more than 60 DEG C after, reactant liquor is poured in boiling water, And 5 times that the volume of boiling water is polyphosphoric acids volume in step A, precipitation is collected by filtration, on a small quantity Water washing precipitation after, precipitation is dissolved in saturated sodium bicarbonate solution, filter, precipitation water Washing, be then dried under vacuum, ethyl alcohol recrystallization obtains 2-(2 '-aminophenyl) benzoxazoles Sterling；
Step C, 2-(2 '-aminophenyl) benzoxazoles and DMAP are dissolved in dry dichloro In methane；
Step D, under argon shield, by the chloro-acetyl chloride that is dissolved in dry methylene chloride by Being added dropwise in above-mentioned mixed solution, stir 2h, rotation is steamed, and mixture uses column chromatography and carries Pure, during purification, eluant is petroleum ether/dichloromethane=2:1, V:V；
Step E, N-hydroxyethyl piperazine and intermediate are mixed after be dissolved in DMF, described DMF solution carries out Non-aqueous processing before using, and is added slowly with stirring a certain amount of Carbon Dioxide Under uniform temperature, 10h is reacted after potassium.
Step F, being cooled to room temperature, be filtrated to get precipitation, filtrate is by ethyl acetate in three times etc. Volume extracts, and merges organic facies, and anhydrous magnesium sulfate is dried, and filters, and column chromatography for separation obtains finally Product, eluant is petrol ether/ethyl acetate=1:1, V:V.
Based on above-mentioned, the hydrogen spectrum of end product copper ion fluorescence probe compound and carbon are composed such as Fig. 1 Shown in, the copper ion fluorescence probe that the present invention provides, dislike with 2-(2 '-aminophenyl) benzo Azoles is fluorescent parent, passes sequentially through and reacts with chloro-acetyl chloride, introduces formoxyl on amino, Obtained intermediate reacts with N-hydroxyethyl piperazine, introduces atom N and hydroxyl, hydroxyl Introduce the water solublity adding this compound, the fluorescence in water can also be strengthened simultaneously.Logical Cross nitrogen-atoms and the oxygen atom carrying out specificity coordination at parent introducing and copper ion, detect process Middle copper ion fluorescence probe can be coordinated with copper ion soon, makes fluorescence weaken rapidly, from And realize detection to copper ion, under the conditions of pH=7.14, fluorescent probe respectively with 15 kinds After common metal ion mixing, fluorescence pattern is as in figure 2 it is shown, illustrate that the probe of this invention is at physiology Under pH, copper ion is had good selectivity.
The copper ion fluorescence probe of this invention and copper ion recognition mechanism are as shown in Fig. 5-2.This machine Reason is through being separately added into 0,0.5,1 times of equivalent with deuterated DMSO for solvent in part CuCl2·2H2O, then surveys its hydrogen spectrum as shown in fig. 5-1 it can be seen that benzoxazoles ring hydrogen Chemical shift there is no and be moved, mainly N-hydroxyethyl piperazine ring hydrogen with The hydrogen on methylene that amide groups is connected, and the hydrogen on hydroxyl there occurs that bigger displacement becomes Change, the hetero atom near these hydrogen and Cu are described2+There occurs coordination.Simultaneously according to fluorescence titration Understand the amount of copper ion and the material of part ratio for 2:1, it is possible to infer that recognition mechanism is Shown in Fig. 5-2.
This probe application copper ion detection example in water body:
Configuration concentration is 1x10-4The copper ion solution of M, solvent is pure water solution.
Configuration concentration is 1x10-4The ligand solution of M, solvent is DMF.
Measure 3mLtris buffer solution (pH=7.14) in fluorescence cuvette, add the most again Enter the probe solution (0.1 μM) of 3 μ L, mix after adding certain volume copper ion solution every time After uniformly (being sequentially added into the amount of copper ion and realizing the amount ratio of copper ion and the material of part is 0.1, 0.2,0.3,0.4,0.5,0.6,0.7,0.8,0.9,1.0,1.2,1.4,1.6,1.8,2.0, 2.2), fluorescence spectrum is measured.Measuring condition: excitation wavelength is 286nm, emission spectrum scope 290-600nm, response curve as it is shown on figure 3, from the response curve of Fig. 3 it can be seen that send out Bright fluorescent probe is to Cu2+The change of concentration has well response, and from Fig. 4, we can Go out when the concentration of copper ion is at 2x10-6-9x10-6In the range of M, linear fit constant is 0.99514, illustrate that the concentration and probe concentration of this invention is 1x10-5During M, can be to 2x10-6-9x10-6M Copper ion in concentration range carries out quantitative analysis.
Measure 3mLtris buffer solution (pH=7.14) in fluorescence cuvette, add the most again Enter the probe solution (0.1 μM) of 3 μ L, be sequentially added into other common metal ion of 15 μ L (1 μM), then adds the copper ion of 3 μ L (0.1 μM), and finally we are by human body Common metal ion is all added in same cuvette, then adds copper ion, all Sample mix uniformly after, measure fluorescence spectrum.Measuring condition: excitation wavelength is 286nm, Emission spectrum scope 290-600nm, the block diagram of gained spectroscopic data as shown in Figure 6, explanation This sensor has extremely strong capacity of resisting disturbance, simultaneously again owing to having preferable selectivity and line Property scope, illustrate the fluorescent probe of this invention be also applicable in life entity detect copper ion.
Skilled person will appreciate that of the industry, the present invention is not restricted to the described embodiments, on State the principle that the present invention is simply described described in embodiment and description, without departing from the present invention On the premise of spirit and scope, the present invention also has various changes and modifications, and these change and change Enter to both fall within scope of the claimed invention.Claimed scope is by appended power Profit claim and equivalent thereof define.

Claims (10)

1. a Cu based on benzoxazoles structure2+Fluorescent probe, it is characterised in that its structure Formula is shown in formula I:
2. a Cu based on benzoxazoles structure as claimed in claim 12+Fluorescent probe Preparation method, it is characterised in that its synthetic route is as follows:
A kind of Cu based on benzoxazoles structure the most according to claim 22+Fluorescent probe Preparation method, it is characterised in that specifically include following processing step:
Step A, ortho-aminobenzoic acid and o-aminophenol are mixed after join in polyphosphoric acids, React some hours at a certain temperature；
Step B, above-mentioned reactant liquor is cooled to uniform temperature after, reactant liquor is poured into water, Precipitation is collected by filtration, after a small amount of water washing precipitation, precipitation is dissolved in alkaline solution, filters, Precipitation washes with water, is then dried, and ethyl alcohol recrystallization obtains 2-(2 '-aminophenyl) benzo and dislikes Azoles sterling；
Step C, 2-(2 '-aminophenyl) benzoxazoles and DMAP are dissolved in dichloromethane；
Step D, that the chloro-acetyl chloride being dissolved in dichloromethane is added dropwise to above-mentioned mixing is molten In liquid, after stirring a period of time, rotation is steamed, and mixture uses column chromatography purification, obtains intermediate Sterling；
Step E, N-hydroxyethyl piperazine and intermediate are mixed after be dissolved in DMF, in stirring Under be slowly added to a certain amount of Anhydrous potassium carbonate after under uniform temperature, react some hours after；
Step F, being cooled to room temperature, be filtrated to get precipitation, filtrate is extracted with ethyl acetate, and closes And organic facies, it being dried, filter, column chromatography for separation obtains end product.
A kind of Cu based on benzoxazoles structure the most according to claim 32+Fluorescent probe Preparation method, it is characterised in that described step A actual conditions is, ortho-aminobenzoic acid and Grind uniformly after adjacent phenalgin phenol mixing, uniform mixture will be ground, join quality for mixing In the polyphosphoric acids that thing is 20 times, then react at 220 DEG C under mechanical agitation, during reaction Between be 3h.
A kind of Cu based on benzoxazoles structure the most according to claim 32+Fluorescent probe Preparation method, it is characterised in that described step B actual conditions is that the temperature of cooling exists More than 60 DEG C, described reactant liquor is poured in boiling water, and the volume of boiling water is polyphosphoric acids volume 5 times, described alkaline solution is saturated sodium bicarbonate solution, described be dried enter under vacuum OK.
A kind of Cu based on benzoxazoles structure the most according to claim 32+Fluorescent probe Preparation method, it is characterised in that described step C actual conditions is, described 2-(2 '-ammonia Base phenyl) benzoxazoles and DMAP be dissolved in dry dichloromethane.
A kind of Cu based on benzoxazoles structure the most according to claim 32+Fluorescent probe Preparation method, it is characterised in that described step D actual conditions is, under argon shield, The chloro-acetyl chloride being dissolved in dry methylene chloride is added dropwise in above-mentioned mixed solution, stirs Mixing 2h, rotation is steamed, and mixture uses column chromatography purification, and during purification, eluant is petroleum ether/bis- Chloromethanes=2:1, V:V.
A kind of Cu based on benzoxazoles structure the most according to claim 32+Fluorescence is visited The preparation method of pin, it is characterised in that described step E actual conditions is, described DMF uses Before carry out Non-aqueous processing, during described reaction a length of 10 hours.
A kind of Cu based on benzoxazoles structure the most according to claim 32+Fluorescence is visited The preparation method of pin, it is characterised in that described step F actual conditions is, described ethyl acetate Extraction three equal-volumes of time-division extraction, described dry time desiccant select anhydrous magnesium sulfate to be dried, During column chromatography for separation, eluant is petrol ether/ethyl acetate=1:1, V:V.
10. an a kind of Cu based on benzoxazoles structure as claimed in claim 12+Fluorescence Probe is in the application in copper ion chemical sensor field, it is characterised in that described Cu2+Fluorescence is visited Pin can be used for the sensing detection of content of copper ion in water environment and human body, and described sensing detection is Fluorescence intensity detects.
CN201610377277.5A 2016-06-01 2016-06-01 Cu<2+> fluorescent probe based on benzoxazole structure and preparation method thereof Pending CN106008389A (en)

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CN112645941A (en) * 2021-01-29 2021-04-13 郑州轻工业大学 Oxazole derivative fluorescent probe and preparation method and application thereof
CN114573519A (en) * 2021-04-14 2022-06-03 三峡大学 Fluorescent probe for copper ion detection and preparation method and application thereof

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107021934A (en) * 2017-05-23 2017-08-08 哈尔滨工业大学（威海） A kind of preparation method of 2 Ben bases Benzooxazole kind compound
CN107021934B (en) * 2017-05-23 2019-12-10 威海创惠环保科技有限公司 Preparation method of 2-phenylbenzoxazole compound
CN111004227A (en) * 2019-12-25 2020-04-14 郑州轻工业大学 Oxazole compound, preparation method thereof and application thereof in Cu detection2+Application of aspects
CN111004227B (en) * 2019-12-25 2021-03-19 郑州轻工业大学 Oxazole compound, preparation method thereof and application thereof in Cu detection2+Application of aspects
CN112645941A (en) * 2021-01-29 2021-04-13 郑州轻工业大学 Oxazole derivative fluorescent probe and preparation method and application thereof
CN114573519A (en) * 2021-04-14 2022-06-03 三峡大学 Fluorescent probe for copper ion detection and preparation method and application thereof
CN114573519B (en) * 2021-04-14 2023-11-21 三峡大学 Fluorescent probe for copper ion detection and preparation method and application thereof

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Application publication date: 20161012