CN108409669A - A kind of synthesis and application of the benzimidazolyl supermolecular gel factor based on Hofmann exhaustive methylation - Google Patents
A kind of synthesis and application of the benzimidazolyl supermolecular gel factor based on Hofmann exhaustive methylation Download PDFInfo
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- CN108409669A CN108409669A CN201810350123.6A CN201810350123A CN108409669A CN 108409669 A CN108409669 A CN 108409669A CN 201810350123 A CN201810350123 A CN 201810350123A CN 108409669 A CN108409669 A CN 108409669A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/0052—Preparation of gels
- B01J13/0065—Preparation of gels containing an organic phase
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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
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- 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
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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
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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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- 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
Abstract
The present invention, which designs, has synthesized a kind of benzimidazolyl supermolecular gel factor based on Hofmann exhaustive methylation, and in the molecule of the gelator, the system that benzimidazole is stablized as a rigid structure, causative subject molecule has issued strong fluorescence；Binding site of the ester group as metal ion is introduced, is acted on by the winding of long alkyl chain, the π pi accumulations between rigid structure group benzimidazole cause gelator to have good state of aggregation fluorescence property as the driving force at gel.The organogel that the gelator is formed in organic solvent forms metal organogel after being combined with iron ion make the fluorescent quenching of organogel, therefore knows Fe with single selective fluorescence3+Performance, and detect limit low, high sensitivity.
Description
Technical field
The present invention relates to a kind of benzimidazolyl supermolecular gel factors, more particularly to one kind being based on the thorough methyl of Huffman
The benzimidazolyl supermolecular gel factor and its synthetic method of change；The invention further relates to the organogels based on the gelator
And metal organogel, it is mainly used for the detection of iron ion, belongs to compound synthesis technical field and ion detection technical field.
Background technology
Iron（Fe）, it is the indispensable trace element of human body, it is the weight for constituting hemoglobin, myoglobins and a variety of enzymes
Ingredient is wanted, if lacking iron in vivo, the synthesis of the red white egg of hemoglobin, flesh can be influenced, certain enzymes can be made, such as cromoci, core
The activity of ribonucleotide reductase, succinate dehydrogenase etc. reduces.These enzymes and biological oxidation, tissue respiration, neurotransmitter
It decomposes and synthesis close relation.Since iron participates in the relationship of hematopoietic function and iron and enzyme, the shortage of iron can cause very
Variation mostly physiologically can cause the reduction of leucocyte sterilizing ability, organism infection to increase, and lymphocyte function is impaired, to
Lead to hypoimmunity, intelligence reduces and body anti-infection ability reduces, and influences body Thermoregulation ability, nervous function is disorderly
Unrest, most commonly hypoferric anemia.In addition, the bleeding of the diseases such as digestive tract ulcer, Enterozoa, and cause asiderosis
Major reason.The problems such as shortage of internal ferro element can generally cause lymph enlargement, hypoferric anemia and edema of limbs.Cause
This, the detection of iron ion is in the fields such as environment measuring and life science important in inhibiting.
Currently, the method that people have been developed for various ionic/molecular detection, and since fluorescence method has operation letter
Just, fast, high sensitivity the advantages that, have developed into ion/molecular identification predominantly detect means.In recent years, chemical sensitisation
The design synthesis of device more causes the concern of people.However, in actual life, various beneficial to human body or harmful ion/
Molecule is mostly present in water phase, and what is reported can be to carry out in the solution mostly to the method that ion is detected, right
Limitation is also compared in the detection of ion/molecular.
Invention content
The benzimidazolyl supermolecular gel factor based on Hofmann exhaustive methylation that the object of the present invention is to provide a kind of
And its synthetic method；
It is a further object of the present invention to provide a kind of organogels based on the above-mentioned supermolecular gel factor；
It is a further aim of the invention a kind of organogel based on above-mentioned gelator of offer is in colorimetric-fluorescence identifying
The concrete application of iron ion.
One, the benzimidazolyl supermolecular gel factor
The present invention is based on the benzimidazolyl supermolecular gel factor chemical names of Hofmann exhaustive methylation to be known as：N-methoxyl group
Carbonyl methyl -2- undecyl benzimidazole salt compounded of iodine, is labeled as：BM-11.Its molecular formula is：C22H35N2O2I, structural formula are：
The preparation of supermolecular gel factor B M-11：Using acetonitrile as solvent, 2- undecyl -1H- benzimidazole -3- methyl acetates
With iodomethane with 1:1~1:3 molar ratio reacts 30 ~ 32h at 85 ~ 90 DEG C；It is cooled to room temperature, is filtered except molten after reaction
Agent is recrystallized with alcohol-water, and it is supermolecular gel factor B M-11 to obtain white solid product.The matter of sensor molecule BM-11
Spectrogram is shown in Fig. 1.
In the molecule of supermolecular gel factor B M-11, the system that benzimidazole is stablized as a rigid structure causes
Host molecule has issued strong fluorescence；Binding site of the ester group as metal ion is introduced, is acted on by the winding of long alkyl chain,
Pi-pi accumulation between rigid structure group benzimidazole causes gelator to have good aggregation as the driving force at gel
State fluorescence property（AIEE）.
Two, the organogel based on supermolecular gel factor B M-11
Supermolecular gel factor B M-11 is dissolved in organic solvent-water mixed solvent, it is 2 ~ 5 mg/mL's to form BM-11 contents
Solution forms stable white condensed state organogel, is denoted as G-11 after being cooled to room temperature.
In organic solvent-water mixed solvent, organic solvent is acetonitrile, dimethyl sulfoxide (DMSO), n,N-Dimethylformamide or second
Glycol；And in the mixed solvent, the percentage by volume of water is 10 ~ 90%.
By to gelator BM-11 in different organic solvents at gelling ability studies have shown that gelator BM-11
Stable organogel system can be formed in above-mentioned organic solvent-water mixed solvent.Since BM-11 is in ethylene glycol-water
It is more stable, the preferred ethylene glycol-water of organic solvent.
Three, applications of the organogel G-11 in ion detection
1, fluorescence properties of the organogel G-11 in different water cut system
Fig. 2 is fluorescence properties of the organogel G-11 in the different water cut system of ethylene glycol-water.As can be seen that with aqueous
Amount is gradually increased from 0 ~ 90%, and the fluorescence of organogel G-11 gradually increases, and at aqueous 90%, fluorescence reaches maximum.Therefore, exist
In subsequent a series of experiments, select in ethylene glycol-water（Water is 90%）The middle mass volume ratio that formed is the organic of 2 ~ 5 mg/mL
Gel G-11.
2, the fluorescence property of organogel G-11
Fig. 3 is the fluorescence emission spectrum of organogel G-11.From the figure 3, it may be seen that organogel G-11 has good fluorescent emission
Performance.When excitation wavelength is 340nm, organogel G-11 sends out white fluorescent（Launch wavelength 472nm）.
3, responses of the organogel G-11 to cation
2 times of moles are separately added into organogel G-11（Relative to gelator BM-11）Mg2+、Ca2+、Cr3+、Fe3 +、Co2+、Ni2+、Cu2+、 Zn2+、Ag+、Cd2+、Hg2+、Pb2+、Ba2+、Tb3+、Al3+、La3+、Eu3+Aqueous solution（It is a concentration of
0.1M）, it is found that only Fe3+Addition can cause organogel G-11 fluorescent quenchings（See Fig. 4）, and it is other cation plus
Similar fluorescent quenching performance cannot be generated by entering.Therefore, organogel G-11 can be realized to Fe3+Single selective response.
Organogel G-11 is to Fe3+Open hole test：2 times of moles are separately added into organogel G-11（Relative to
BM-11）Fe (III) salt, the response of observation organogel G-11.As a result, it has been found that with the slowly passage of time, Fe (III) salt
Slowly infiltration, organogel G-11 are gradually destroyed, and the color of organogel is changed into light yellow, organogel G-11 by white
With Fe3+Complexing forms metal organogel G-Fe.
4, organogel G-11 is to Fe3+Fluorescence titration
The fluorescence titration that Fig. 5 is organogel G-11 is tested.When excitation wavelength is 340nm, G-11 sends out almost white glimmering
Light（Launch wavelength 476nm）.With Fe3+Gradually increase, the fluorescence of organogel G-11 almost quenches.G-11 pairs of organogel
Fe3+Detection be limited to 3.08 × 10-7M。
5, organogel G-11 is to Fe3+Fluorescence identifying basis mechanism
Shown by infrared experiment（See Fig. 6）, in G-11, the peaks C-N and the peaks C=O are respectively in 1621 cm-1With 1752 cm-1
Place；Fe is added in G-113+When, the peaks C-N and the peaks C=O are by 1621 cm-1With 1752 cm-1It is moved respectively to 1656 cm-1With
1757cm-1, this illustrates Fe3+It is coordinated with the C-N of G-11 and-C=O.
In order to study the existence of organogel G-11 and metal organogel G-Fe, the inspection of scanning electron microscope has been done to it
It surveys.SEM is carried out under conditions of having done metal spraying processing to organogel G-11 and metal organogel G-Fe.As a result as schemed
Shown in 7, it is found that organogel G-11 exists with the block structure that is overlapped, when Fe is added thereto3+Form metal organogel G-
After Fe, state occurs transformation and is destroyed.
In conclusion to have synthesized a kind of benzimidazole based supermolecular based on Hofmann exhaustive methylation solidifying for present invention design
The glue factor, in the molecule of the gelator, the system that benzimidazole is stablized as a rigid structure, causative subject molecule is sent out
Strong fluorescence；Binding site of the ester group as metal ion is introduced, is secondly acted on the winding of long alkyl chain, rigid structure base
Pi-pi accumulation between group's benzimidazole causes gelator to have good state of aggregation fluorescence property as the driving force at gel
（AIEE）.The organogel that the gelator is formed in organic solvent-water mixed solvent forms metal after being combined with iron ion
Organogel makes the fluorescent quenching of organogel, and the organogel which forms in organic solvent is combined with iron ion
Forming metal organogel afterwards makes the fluorescent quenching of organogel, therefore knows Fe with single selective fluorescence3+Performance.
Description of the drawings
Fig. 1 is the mass spectrogram of gelator BM-11 prepared by the present invention.
Fig. 2 is fluorescence emission spectrums of the organogel G-11 in different water cut system in ethylene glycol-water.
Fig. 3 is fluorescence emission spectrums of the organogel G-11 in ethylene glycol-water.
Fig. 4 is the fluorescence spectrum when metal cation of 2 times of moles being added in organogel G-11（Excitation wavelength
340nm）.
Fig. 5 is organogel G-11 in Fe3+In fluorescence emission spectrum.
Fig. 6 is organogel G-11, the IR of metal organogel G-Fe schemes.
Fig. 7 is organogel G-11, the SEM of metal organogel G-Fe schemes.
Specific implementation mode
Below by specific embodiment to the synthesis of inventive gel factor B M-11, organogel G-11 and its colorimetric/
The application of fluorescence identifying iron ion is described further.
The preparation of embodiment 1, gelator BM-11
In 50 ml acetonitriles, 1.03 g are added（3 ×10-3 mol）2- undecyl -1H- benzimidazole -3- methyl acetates,
1.27 g（9×10-3 mol）Iodomethane reacts 32 h at 85 DEG C；It is cooled to room temperature after reaction, filters and remove solvent, use
Alcohol-water recrystallizes, and it is sensor molecule BM-11, yield 53.9% to obtain white solid product.The mass spectrogram of BM-11 is shown in figure
1。
The formation of embodiment 2, organogel G-11
Gelator BM-11 0.005g prepared by Example 1, are added to 1.00 mL glycol/waters（v/v=1:9）In, add
Heat makes it fully dissolve, and stands, and the white condensed state that the stabilization that mass volume ratio is 5mg/mL is formed after being cooled to room temperature is organic
Gel G-11.Under the ultraviolet lamp of 356nm, organogel G-11 sends out white fluorescent.
Embodiment 3, organogel G-11 colorimetrics/fluorescence identifying iron ion
In the spot plate of organogel G-11 a series of, it is separately added into Mg2+、Ca2+、Cr3+、Fe3+、Co2+、Ni2+、Cu2+、 Zn2 +、Ag+、Cd2+、Hg2+、Pb2+、Ba2+、Tb3+、Al3+、La3+And Eu3+The aqueous solution of cation（A concentration of 0.1M）If organogel
The fluorescent quenching of G-11, and organogel color be changed by white it is light yellow, then illustrate be added dropwise be Fe3+If organogel
Fluorescence do not quench, then illustrate be added dropwise be not Fe3+。
Claims (8)
1. a kind of benzimidazolyl supermolecular gel factor based on Hofmann exhaustive methylation, structural formula are：
。
2. the synthesis side of the benzimidazolyl supermolecular gel factor based on Hofmann exhaustive methylation as described in claim 1
Method is the 2- undecyl -1H- benzimidazoles using acetonitrile as solvent, and 3- methyl acetates and iodomethane are substrate, at 85 ~ 90 DEG C
React 30 ~ 32h；It is cooled to room temperature after reaction, filters and remove solvent, recrystallized with alcohol-water, obtain white solid product i.e.
It can.
3. the synthesis side of the benzimidazolyl supermolecular gel factor based on Hofmann exhaustive methylation as described in claim 1
Method, it is characterised in that：The molar ratio of substrate 2- undecyl -1H- benzimidazole 3- methyl acetates and iodomethane is 1:1~1:3.
4. a kind of organogel based on the supermolecular gel factor as described in claim 1 is by the supermolecular gel factor
The solution for forming that supermolecular gel factor content is 2 ~ 5 mg/mL in the in the mixed solvent of organic solvent-water is dissolved by heating, it is cold
But to forming stable condensed state organogel after room temperature.
5. organogel as claimed in claim 4, it is characterised in that：Organogel has good fluorescent emission performance, when
When excitation wavelength is 340nm, organogel sends out white fluorescent, and gradually increasing in the mixed solvent water content, organic
The fluorescence of gel also gradually increases.
6. organogel as described in claim 4 or 5, it is characterised in that：The in the mixed solvent of organic solvent-water, You Jirong
Agent is one kind of acetonitrile, ethylene glycol, dimethyl sulfoxide (DMSO), N,N-dimethylformamide；The volume ratio of organic solvent and water is 1:1~
1:9。
7. organogel as claimed in claim 4 is used for fluorescence identifying iron ion.
8. organogel as described in claim 1 is used for fluorescence identifying iron ion, it is characterised in that：In a series of organogel points
It drips in plate, is separately added into Mg2+、Ca2+、Cr3+、Fe3+、Co2+、Ni2+、Cu2+、 Zn2+、Ag+、Cd2+、Hg2+、Pb2+、Ba2+、Tb3+、
Al3+、La3+、Eu3+Aqueous solution, if the fluorescent quenching of organogel, gel color is changed into khaki by white, illustrates to be added dropwise
Be Fe3+；If the fluorescence and color of organogel do not change, that illustrate to be added dropwise is not Fe3+。
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Cited By (2)
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| CN109705368A (en) * | 2018-12-24 | 2019-05-03 | 西北师范大学 | A kind of supermolecule and preparation method thereof based on benzimidazole iodo salt |
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