CN105693655A - Aminobenzothiazole-modified column aromatic hydrocarbons and synthesis thereof, and application of column aromatic hydrocarbons in continuous fluorescent recognition of Fe<3+> and F<-> in water phase - Google Patents

Aminobenzothiazole-modified column aromatic hydrocarbons and synthesis thereof, and application of column aromatic hydrocarbons in continuous fluorescent recognition of Fe<3+> and F<-> in water phase Download PDF

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CN105693655A
CN105693655A CN201610199037.0A CN201610199037A CN105693655A CN 105693655 A CN105693655 A CN 105693655A CN 201610199037 A CN201610199037 A CN 201610199037A CN 105693655 A CN105693655 A CN 105693655A
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aromatic hydrocarbons
aminobenzothiazole
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魏太保
程晓斌
李辉
张有明
林奇
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Northwest Normal University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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    • 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"
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    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • 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"
    • G01N2021/6432—Quenching

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Abstract

The invention provides aminobenzothiazole-modified column aromatic hydrocarbons PF5 which are formed by introducing 2-aminobenzothiazole into alkoxy structures on both ends of column 5 aromatic hydrocarbons. The fluorescent recognition performance indicates that only the addition of Fe<3+> can completely quench the blue fluorescence of the PF5 solution under an ultraviolet lamp, and the addition of other cations almost has no influence on the fluorescence of the PF5 solution, which indicates that the PF5 can perform high-selectivity single detection on Fe<3+>. The further research indicates that in the solution of the complex PF5-Fe<3+> formed by PF5 and Fe<3+>, only the addition of the F<-> can restore the blue fluorescence of the PF5-Fe<3+> solution, and the addition of other anions can not obviously change the PF5-Fe<3+> DMSO (dimethyl sulfoxide)/H2O solution color and fluorescence spectrum. Therefore, the aminobenzothiazole-modified column aromatic hydrocarbons can be used as a sensor for continuous fluorescent recognition of Fe<3+> and F<-> in a water phase.

Description

Post aromatic hydrocarbons that aminobenzothiazole is modified and synthesis and Fe in continuous fluorescence identification aqueous phase3+、F-Application
Technical field
The present invention relates to functionalization post aromatic hydrocarbons of a kind of aminobenzothiazole modification and preparation method thereof；The present invention also relates to this functionalization post aromatic hydrocarbons fluorescence continuous detecting Fe in Aquo System3+And F-Application, belong to technical field of macromolecules and ion detection technical field。
Background technology
Post aromatic hydrocarbons, as a new generation's macrocycle molecule main body, is by Isosorbide-5-Nitrae-position methylene-bridged, the high molecular polymer that structure height is symmetrical。Compared to crown ether, cyclodextrin, calixarenes has better symmetry and rigid structure, and this special structure makes them that object have the selectivity of uniqueness。Therefore, post aromatic hydrocarbons has shown very outstanding effect as the macrocycle molecule that a class is new in host-guest chemistry。By the modification of coupled columns aromatic hydrocarbons structure, many host-guest chemistry systems are well developed。
In biological and environmental science, high selectivity, efficient chemical sensor development just day by day receive the concern of people, people have focused onto in the research of this kind of sensor more and more。Design and synthesis one class hypersensitivity, height optionally fluorescent probe are organic and a most basic target of AC。Ferrum is the element of a kind of needed by human, and it plays an important role in all of active somatic cell。It is present in the middle of the structure of many enzymes and protein, and therefore it is requisite in the metabolic processes of life entity, and a lot of cell biologicals and chemical reaction are required for its addition。Once human body lacks ferrum, a lot of diseases will be following, such as common iron deficiency anemia。But, concentration of iron is too high is disadvantageous to life entity equally。There are some researches show, the generation of some tumor, diabetes etc. is relevant all with it。Therefore, ensure that in human health, the detection of iron ion is highly important at control loop environment pollution。It is known that fluorion aspect and the important anion as biological metabolism, play an important role in life process。But excessively picked-up can cause fluorosis, therefore that the detection of fluorion is significant, the simplicity of fluorion, method for quick show more and more important in clinical treatment。Owing to detection technique of fluorescence has convenient and swift, highly sensitive, good selective, substantial amounts of work concentrates on the fluorescence molecule designing and synthesizing the fluorescence signal effective expression that molecular recognition event can be passed through molecule。
Summary of the invention
It is an object of the invention to provide the post aromatic hydrocarbons that a kind of aminobenzothiazole is modified；
It is a further object of the present invention to provide the synthetic method of the post aromatic hydrocarbons that a kind of aminobenzothiazole is modified；
Another object of the present invention, it is simply that post aromatic hydrocarbons continuous detecting Fe in Aquo System that aminobenzothiazole is modified is provided3+And F-Application。
One, the post aromatic hydrocarbons that 2-aminobenzothiazole is modified
The post aromatic hydrocarbons that 2-aminobenzothiazole of the present invention is modified, is that the alkoxide in post 5 aromatic hydrocarbons one end introduces 2-aminobenzothiazole so that it is producing strong blue-fluorescence, be labeled as PF5, its structural formula is as follows:
。
Two, the synthesis of the post aromatic hydrocarbons that 2-aminobenzothiazole is modified
(1) synthesis of monolateral post 5 aromatic hydrocarbons: with 1,2-dichloroethanes for solvent, boron trifluoride diethyl etherate is catalyst, paraformaldehyde, 1-(4-bromobutyl oxygen)-4-methoxybenzene and terephthaldehyde's ether is raw material, in room temperature reaction 0.6～1h；Reaction uses methanol extraction after terminating, and chloroform dissolves, and distilled water extracts, and dried organic facies pillar layer separation obtains monolateral post 5 aromatic hydrocarbons；
Paraformaldehyde, 1-(4-bromobutyl oxygen)-4-methoxybenzene, terephthaldehyde's ether mol ratio be 5:1:5 ~ 5:5.1:5.2；
The consumption of catalyst boron trifluoride diethyl etherate is 0.1 ~ 0.5 times of paraformaldehyde mole。
(2) synthesis of the post aromatic hydrocarbons that hydroxy benzaldehyde is modified: with oxolane for solvent, KOH is catalyst, monolateral post 5 aromatic hydrocarbons and hydroxy benzaldehyde, with the mol ratio of 1:1 ~ 1:1.2, are stirred at room temperature reaction 65 ~ 70h；Decompression is distilled off solvent, goes out white solid with elutriation, is the post aromatic hydrocarbons that hydroxy benzaldehyde is modified；The consumption of catalyst KOH is 1 ~ 1.2 times of hydroxy benzaldehyde mole。
(3) synthesis of the post aromatic hydrocarbons that 2-aminobenzothiazole is modified: with ethanol for solvent, the post aromatic hydrocarbons that hydroxy benzaldehyde is modified and the 2-aminobenzothiazole mol ratio with 1:1 ~ 1:1.2, in 75 ~ 80 DEG C of stirring reaction 36 ~ 48h；It is cooled to room temperature, sucking filtration after having reacted, dries, obtain white solid and be the post aromatic hydrocarbons that target product 2-aminobenzothiazole is modified, be labeled as PF5。
The synthetic route of the post aromatic hydrocarbons that 2-aminobenzothiazole is modified is as follows:
。
Three, the post aromatic hydrocarbons fluorescence identifying performance that aminobenzothiazole is modified
1, the research to cationic fluorescent recognition performance
Draw the DMSO solution (2 × 10 of the post aromatic hydrocarbons PF5 that 0.5mL2-aminobenzothiazole is modified respectively-3Mol/L) in a series of 10mL color comparison tubes, Fe then it is separately added into again3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+DMSO solution (0.004mol L-1) 0.5mL, add distilled water 1mL, then be diluted to 5mL with DMSO, now the concentration of PF5 is 2 × 10-4mol·L-1, cationic concentration is 10 times of PF5 concentration, observes PF5 to each cationic response (Fig. 1)。
Find under uviol lamp, only Fe3+Addition make the complete quencher of blue-fluorescence of PF5 solution。In corresponding fluorescence spectrum, only Fe3+Addition make the fluorescence disappearance of launching wavelength at 432nm place, and other cationic addition on the fluorescence of PF5 solution almost without impact。Illustrate that PF5 is at DMSO/H2(H in O system2The percentage by volume of O is 20 ~ 25%) can high selectivity single detection Fe3+。
2, the titration to iron ion
Pipette the DMSO/H of 2.0mLPF52O=8:2 solution (2.0 × 10-4Mol/L) in quartz cell, it is gradually added into Fe by accumulation application of sample method3+DMSO solution, in 25 DEG C survey its fluorescence emission spectrum (Fig. 2)。Titration experiments illustrates, the fluorescence intensity of PF5 is subject to the impact of iron concentration, weakens along with the increase of iron concentration。And obtain the PF5 detection to the fluorescence spectrum of iron ion according to titration experiments and be limited to 9.0 × 10-7Mol/L (Fig. 3)。Thus illustrate, compound PF5 in water solution system still can single selective fluorescence identifying iron ion, and the detection sensitivity of iron ion is significantly high。
3, to Anion Recognition performance
Pipette the DMSO/H of 0.5mL receptor PF5 respectively2O=8:2 solution (2 × 10-3mol·L-1) in a series of 10mL color comparison tubes, it is separately added into 0.5mLFe3+Form complex PF5-Fe3+, then it is separately added into F again-, Cl-, Br-, I-, AcO-, HSO4 -, ClO4 -, CN-、SCN-, NO3 -DMSO solution (0.01mol L-1) 0.5mL, add the distilled water of 1mL, then be diluted to 5mL with DMSO。Now PF5-Fe3+Concentration is 2 × 10-4mol·L-1, anion concentration is 100 times of acceptor density。Observe PF5-Fe3+Response to each anion。
It was found that in fluorescence spectrum, only F-Addition make PF5-Fe3+DMSO/H2O(v/v=8:2) there is maximum fluorescence emission peak (λ at 432nm place in solutionex=360nm)；Under uviol lamp, only F-Addition make PF5-Fe3+DMSO/H2O solution sends blue-fluorescence, and the addition of other anion, PF5-Fe3+DMSO/H2O solution colour and fluorescence spectrum do not have any obvious change (Fig. 4), and PF5-Fe is described3+To F-Show very strong single-minded selectivity, therefore can high selectivity, highly sensitive fluorescence identifying F-。
4, receptor PF5-Fe3+Titration
Pipette 2.0mLPF5-Fe3+DMSO/H2O solution (2.0 × 10-4Mol/L) in quartz cell, it is gradually added into F by accumulation application of sample method-The solution of DMSO。Its fluorescence emission spectrum (Fig. 5) is surveyed in 25 DEG C。Titration experiments illustrates, PF5-Fe3+Fluorescence intensity be subject to the impact of fluorinion concentration, and strengthen along with the increase of fluorinion concentration。And obtain PF5-Fe according to titration experiments3+The detection of the fluorescence spectrum of fluorion is limited to 2.59 × 10-8Mol/L(Fig. 6)。Thus illustrate, compound PF5-Fe3 +At DMSO/H2Energy single selective fluorescence identifying fluorion in O system, and the detection sensitivity of fluorion is significantly high。
Accompanying drawing explanation
Fig. 1 is the fluorescence spectrum (excitation wavelength: 360nm launches wavelength 432nm) when PF5 and its addition cation。
Fig. 2 is the Fe of variable concentrations3+There is the fluorescence spectrum of lower receptor PF5 in (0-40 times)。
Fig. 3 is the Fe of variable concentrations3+(0-40 times) exists lower to Fe3+/ PF5 fitting a straight line。
Fig. 4 is PF5+Fe3+And the fluorescence spectrum (excitation wavelength: 360nm launches wavelength: 432nm) during its addition anion。
Fig. 5 is the F of variable concentrations-There is lower receptor PF5+Fe in (0-1.5 times)3+Fluorescence spectrum。
Fig. 6 is the F of variable concentrations-(0-1.5 times) exists lower to F-/ (PF5+Fe3+) fitting a straight line。
Detailed description of the invention
The synthesis of post aromatic hydrocarbons, structure and the fluorescence identifying application 2-aminobenzothiazole of the present invention modified below by specific embodiment are described further。
1, the synthesis of the post aromatic hydrocarbons that 2-aminobenzothiazole is modified
(1) synthesis of monolateral post 5 aromatic hydrocarbons: take 1-(4-bromobutyl oxygen)-4-methoxybenzene (1.32g, 5mmol), terephthaldehyde's ether (2.76g, 20mmol), join 80mL1, in 2 dichloroethanes, after stirring and dissolving, add paraformaldehyde (0.75g, 25mmol), boron trifluoride diethyl etherate (3.2mL, 25mmol), at room temperature reacts 1h；Reaction is poured into after terminating in methanol and is precipitated out precipitation, filters precipitation, dissolves with chloroform, distilled water 30ml × 3 time extract, and dry organic facies, with pillar layer separation (petrol ether/ethyl acetate (v/v)=50:1), obtain white solid and be monolateral post 5 aromatic hydrocarbons (1.2g), yield 25%。
1HNMR(600MHz,CDCl3)δ6.93–6.63(m,10H),3.89(d,J=6.5Hz,1H),3.83(t,J=6.0Hz,1H),3.81–3.75(m,10H),3.75–3.55(m,27H),3.42(d,J=130.4Hz,2H),1.92(s,1H),1.81(s,1H),1.25(s,2H)。
(2) synthesis of the post aromatic hydrocarbons that hydroxy benzaldehyde is modified: take KOH(0.056g, 1.0mmol), hydroxy benzaldehyde (0.122g, 1.0mmol), joins in 30mLTHF and dissolves, it is added thereto to monolateral post 5 aromatic hydrocarbons (0.88g again, 1.0mmol), reaction 72h being stirred at room temperature, decompression distills solvent, the precipitation white solid that adds water is the post aromatic hydrocarbons (0.6g) that hydroxy benzaldehyde is modified, productivity 60%。
1HNMR(600MHz,CDCl3)δ8.81(s,1H),7.01–6.55(m,14H),3.79(s,10H),3.71–3.64(m,27H),3.34(d,J=6.8Hz,4H),1.89(d,J=56.8Hz,4H)。
(3) synthesis of the post aromatic hydrocarbons that 2-aminobenzothiazole is modified: take the post aromatic hydrocarbons (0.456g that hydroxy benzaldehyde is modified, 0.5mmol), 2-aminobenzothiazole (0.075g, 0.5mmol), joins in 30mL ethanol and dissolves, 80 DEG C are stirred at reflux reaction 48h, room temperature it is cooled to after having reacted, sucking filtration, after drying, obtain white solid and be target product PF5(0.48g), productivity 90%。
1HNMR(400MHz,CDCl3)δ7.97(s,1H),6.92–6.60(m,18H),3.77(s,10H),3.66(d,J=6.3Hz,27H),3.49(s,2H),3.22(s,2H),1.80(s,4H).13CNMR(101MHz,CDCl3)δ150.83,128.41,114.00,67.62,55.88,29.71,27.35.ESI-MSm/z:[M+H]+Calcdfor1044;Found1045.49。
2、Fe3+、F-Detection
Fe3+Detection: pipette the DMSO/H of PF52O(v/v=8:2) solution (2 × 10-3mol·L-1) in a series of 10mL color comparison tubes, it is separately added into Fe3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+DMSO solution (4 × 10-3mol·L-1) 0.5mL, if the complete quencher of the blue-fluorescence of solution, then that addition is described is Fe3+；If the fluorescence color of solution does not change, what addition was described is other cation。
F-Detection: pipette the DMSO solution (2 × 10 of PF5-3mol·L-1) in a series of 10mL color comparison tubes, first it is separately added into Fe3+, the blue quencher of solution；It is separately added into F more wherein-, Cl-, Br-, I-, AcO-, HSO4 -, ClO4 -, CN-, SCN-, NO3 -Solution, if the blue-fluorescence of solution recovers, then that addition is described is F-；If the blue-fluorescence of solution does not recover (fluorescence does not change), then that addition is described is not F-。

Claims (9)

  1. The post aromatic hydrocarbons that 1.2-aminobenzothiazole is modified, its structural formula is as follows:
    。
  2. 2. the synthesis of the post aromatic hydrocarbons that 2-aminobenzothiazole as claimed in claim 1 is modified, comprises the following steps that:
    (1) synthesis of monolateral post 5 aromatic hydrocarbons: with 1,2-dichloroethanes for solvent, boron trifluoride diethyl etherate is catalyst, paraformaldehyde, 1-(4-bromobutyl oxygen)-4-methoxybenzene and terephthaldehyde's ether is raw material, in room temperature reaction 0.6～1h；Reaction uses methanol extraction after terminating, and chloroform dissolves, and distilled water extracts, and dried organic facies pillar layer separation obtains monolateral post 5 aromatic hydrocarbons；
    (2) synthesis of the post aromatic hydrocarbons that hydroxy benzaldehyde is modified: with oxolane for solvent, KOH is catalyst, monolateral post 5 aromatic hydrocarbons and hydroxy benzaldehyde are stirred at room temperature reaction 65 ~ 70h；Decompression is distilled off solvent, goes out white solid with elutriation, is the post aromatic hydrocarbons that hydroxy benzaldehyde is modified；
    (3) synthesis of the post aromatic hydrocarbons that 2-aminobenzothiazole is modified: with ethanol for solvent, the post aromatic hydrocarbons that hydroxy benzaldehyde is modified and 2-aminobenzothiazole are in 75 ~ 80 DEG C of stirring reaction 36 ~ 48h；It is cooled to room temperature, sucking filtration after having reacted, dries, obtain white solid and be the post aromatic hydrocarbons that target product 2-aminobenzothiazole is modified。
  3. 3. the synthesis of the as claimed in claim 2 post aromatic hydrocarbons that 2-aminobenzothiazole is modified, it is characterised in that: in step (1), paraformaldehyde, 1-(4-bromobutyl oxygen)-4-methoxybenzene, terephthaldehyde's ether mol ratio be 5:1:5 ~ 5:1.1:5.2。
  4. 4. the synthesis of the post aromatic hydrocarbons that 2-aminobenzothiazole as claimed in claim 2 is modified, it is characterised in that: in step (1), the consumption of catalyst boron trifluoride diethyl etherate is 0.1 ~ 0.5 times of paraformaldehyde mole。
  5. 5. the synthesis of the post aromatic hydrocarbons that 2-aminobenzothiazole as claimed in claim 2 is modified, it is characterised in that: in step (2), the mol ratio of monolateral post 5 aromatic hydrocarbons and hydroxy benzaldehyde is 1:1 ~ 1:1.2。
  6. 6. the synthesis of the post aromatic hydrocarbons that 2-aminobenzothiazole as claimed in claim 2 is modified, it is characterised in that: in step (2), the consumption of catalyst KOH is 1 ~ 1.2 times of hydroxy benzaldehyde mole。
  7. 7. the synthesis of the post aromatic hydrocarbons that 2-aminobenzothiazole as claimed in claim 2 is modified, it is characterised in that: in step (3), post aromatic hydrocarbons and the mol ratio of 2-aminobenzothiazole that hydroxy benzaldehyde is modified are 1:1 ~ 1:1.2。
  8. 8. the post aromatic hydrocarbons that 2-aminobenzothiazole is modified as claimed in claim 1 divides for continuous fluorescence identification Fe as sensor3 +, it is characterised in that: at the DMSO/H of the post aromatic hydrocarbons that 2-aminobenzothiazole is modified2In O solution, it is separately added into Fe3+, Hg2+, Ag+, Ca2+, Cu2+, Co2+, Ni2+, Cd2+, Pb2+, Zn2+, Cr3+, Mg2+Solution, if the complete quencher of the blue-fluorescence of solution, then that addition is described is Fe3+；If the fluorescence color of solution does not change, what addition was described is other cation。
  9. 9. the post aromatic hydrocarbons that 2-aminobenzothiazole is modified as claimed in claim 1 can be used for continuous fluorescence identification F as sensor-, it is characterised in that: at the DMSO/H of the post aromatic hydrocarbons that 2-aminobenzothiazole is modified2In O solution, it is initially charged Fe3+, the blue quencher of solution；It is separately added into F more wherein-, Cl-, Br-, I-, AcO-, HSO4 -, ClO4 -, CN-, SCN-, NO3 -Solution, if the blue-fluorescence of solution recovers, then that addition is described is F-；If the fluorescence of solution does not change, then that addition is described is not F-。
CN201610199037.0A 2016-04-01 2016-04-01 Aminobenzothiazole-modified column aromatic hydrocarbons and synthesis thereof, and application of column aromatic hydrocarbons in continuous fluorescent recognition of Fe<3+> and F<-> in water phase Pending CN105693655A (en)

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CN109655436A (en) * 2018-12-07 2019-04-19 武汉工程大学 Cryanide ion fluorescence detection test of a kind of column aromatic hydrocarbons modification and preparation method thereof, detection method
CN109655436B (en) * 2018-12-07 2021-03-30 武汉工程大学 Column aromatic modified cyanide ion fluorescence detection test paper, and preparation method and detection method thereof
CN109851809A (en) * 2019-03-12 2019-06-07 华东师范大学 A kind of column [5] aromatic monomer and its homopolymer and preparation method
CN109851809B (en) * 2019-03-12 2019-09-17 华东师范大学 A kind of column [5] aromatic monomer and its homopolymer and preparation method
CN111517947A (en) * 2020-03-18 2020-08-11 西北师范大学 Bilateral column [5] arene sensor molecule based on functionalization and synthesis and application thereof
CN111423365A (en) * 2020-04-03 2020-07-17 华东师范大学 Bifunctional group pillar aromatic hydrocarbon derivative ligand, metal organic cage and preparation method
CN112409292A (en) * 2020-11-27 2021-02-26 太原理工大学 Multifunctional fluorescent probe, preparation method and application
CN112409292B (en) * 2020-11-27 2022-05-17 太原理工大学 Multifunctional fluorescent probe, preparation method and application
CN115672295A (en) * 2022-11-05 2023-02-03 中国科学院兰州化学物理研究所 Preparation and application of imine column [5] arene modified silica gel chromatographic packing
CN115672295B (en) * 2022-11-05 2023-12-15 中国科学院兰州化学物理研究所 Preparation and application of imine type column [5] arene modified silica gel chromatographic packing

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