CN113248443A - Tridentate benzimidazole salt compound and preparation method and application thereof - Google Patents
Tridentate benzimidazole salt compound and preparation method and application thereof Download PDFInfo
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- CN113248443A CN113248443A CN202110599361.2A CN202110599361A CN113248443A CN 113248443 A CN113248443 A CN 113248443A CN 202110599361 A CN202110599361 A CN 202110599361A CN 113248443 A CN113248443 A CN 113248443A
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- -1 benzimidazole salt compound Chemical class 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229940125782 compound 2 Drugs 0.000 claims abstract description 12
- 229940126214 compound 3 Drugs 0.000 claims abstract description 12
- QSECPQCFCWVBKM-UHFFFAOYSA-N 2-iodoethanol Chemical compound OCCI QSECPQCFCWVBKM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229940125904 compound 1 Drugs 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000002189 fluorescence spectrum Methods 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007850 fluorescent dye Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 238000004639 Schlenk technique Methods 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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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
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- 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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- 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
The invention discloses a tridentate benzimidazole salt compound and a preparation method and application thereof. The compound 2 is obtained by reacting the compound 1 with benzimidazole in an organic solvent. And reacting the compound 2 with 2-iodoethanol to obtain a compound 3. Using 3 as a host and different TBA salts as objects, dissolving the host and the objects in an organic solvent at 25 ℃, mixing the host solution and different object solutions respectively at a certain concentration, measuring fluorescence spectra of the solutions, and finding out the objects which can be identified by the host. For the guest that can be recognized by the host, the host is titrated with different concentrations of the guest, and the fluorescence spectrum thereof is measured. The fluorescent host compound 3 has the advantages of simple preparation and obvious fluorescent photosensitive effect, can be used for manufacturing a fluorescent molecule recognition system, and is expected to be applied to the field of fluorescent chemistry.
Description
Statement regarding sponsoring research or development
The invention is carried out under the subsidies of Tianjin City natural science fund (fund number: 18JCZDJC 99600), national natural science fund (fund number: 21572159) and Tianjin Master university youth fund (fund number: 52XQ 1402).
Technical Field
The invention belongs to the technical field of organic chemistry, and relates to a benzimidazole salt compound taking 4, 4', 4' ' -methylene trisphenol derivatives, benzimidazole and 2-iodoethanol as raw materials, in particular to a preparation method of a tridentate benzimidazole salt compound and research on fluorescence recognition performance of the tridentate benzimidazole salt compound.
Background
The fluorescent probe recognizing the specific chemical substance outputs microscopic recognition information in the form of a fluorescent signal. The fluorescent probe has the advantages of high sensitivity, small interference from external conditions, simple and convenient operation and the like. Fluorescent probes are therefore widely used to detect various ionic or harmful contaminants in the environment. The benzimidazole onium salt containing the aromatic ring structure is a compound with a unique structure, and the benzimidazole onium salt can be combined with an object through weak acting force such as hydrogen bonds and has stronger capturing capacity on the object. The compounds can exist stably at higher temperature, so that the compounds have good application prospect as main compounds of fluorescent probes.
Disclosure of Invention
The invention discloses a tridentate benzimidazole salt compound 3 with the following structure:
the invention further discloses a preparation method of the tridentate benzimidazole salt compound, which is characterized by comprising the following steps:
the compound 1 reacts with benzimidazole in an organic solvent to obtain a compound 2. Reacting the compound 2 with 2-iodoethanol to obtain a tridentate compound 3; wherein the molar ratio of the compound 1 to the benzimidazole is 1: 3-1: 6; the molar ratio of the compound 2 to the 2-iodoethanol is 1: 15-1: 20; the organic solvent is selected from one or a mixture of methanol, ethanol and acetonitrile.
The benzimidazole salt compound can be prepared by taking the 4, 4', 4' ' -methylene triphenol derivative, benzimidazole and 2-iodoethanol as raw materials. The compound 2 is obtained by reacting the compound 1 with benzimidazole in an organic solvent. And reacting the compound 2 with 2-iodoethanol to obtain a compound 3.
The benzimidazole salt compound has the advantages of simple preparation and obvious fluorescent photosensitive effect, can be used for preparing a fluorescent molecule recognition system, and is expected to be applied to the field of fluorescent chemistry.
The synthetic route of the invention is as follows:
the invention further discloses the application of the compound 3 as a main body in the field of fluorescence recognition; wherein the fluorescence recognition system is for HSO4 -Identification of (1). The experimental results show that: with compound 3 as host and a different type of tetrabutylammonium salt (TBA salt) as guest (different TBA salts, e.g.: F)-, Cl-, Br-, H2PO4 -, HSO4 -, OAc-And NO3 -) Dissolving a host and an object in an organic solvent at 25 ℃, mixing the host solution with different object solutions respectively at a certain concentration, and measuring the fluorescence spectrum of the mixture to find out the object which can be identified by the host. For the guest that the host can recognize, the host was titrated with different concentrations of guest (5.0 × 10)-6 mol L-1) The fluorescence spectrum was measured. Adding TAB salt solution (0-20X 10) with gradually increasing concentration by microsyringe-6 mol L-1). The excitation wavelength of the main solution is 233 nm, and the emission spectrum has an emission peak at 337 nm. After each addition, reaction equilibrium was reached for 8-10 minutes to determine the corresponding fluorescence intensity. The benzimidazole salt compound as the main body of the invention has obvious fluorescence sensitization effect on the TAB salt compound, has obvious fluorescence emission at 337 nm in a fluorescence spectrum, (figure 2) can be used for manufacturing a fluorescent probe,is expected to be applied in the field of fluorescence chemistry. One preferred embodiment of the present invention is application example 1.
The tridentate benzimidazole salt compound provided by the invention is a fluorescent material which can stably exist in a standard state, has the advantage of obvious fluorescent photosensitive effect, can be used for manufacturing a fluorescent molecule recognition system, and is expected to be applied in the field of fluorescent chemistry.
Description of the drawings:
FIG. 1 is a graph showing the fluorescence spectra of compound 3 (application example 1) at 25 ℃ in acetonitrile/ethanol (v: v = 1:499, v representing volume) solution with different types of TAB salt solutions of the same concentration; from the figure, it can be seen that the subject is to HSO4 -Having selective recognition capability;
FIG. 2 shows the addition of HSO at different concentrations to a solution of Compound 3 (application example 2) in acetonitrile/ethanol (v: v = 1:499, v denotes volume) at 25 deg.C4 -The fluorescence spectrum of the solution (2) can be seen from the graph along with HSO4 -The fluorescence intensity gradually increases when the concentration increases, when HSO4 -After increasing the concentration to a certain value, there was no longer a significant decrease in fluorescence.
Detailed Description
The invention is described below by means of specific embodiments. Unless otherwise specified, the technical means used in the present invention are well known to those skilled in the art. In addition, the embodiments should be considered illustrative, and not restrictive, of the scope of the invention, which is defined solely by the claims. It will be apparent to those skilled in the art that various changes or modifications in the components and amounts of the materials used in these embodiments can be made without departing from the spirit and scope of the invention.
The raw materials and reagents used in the invention are commercially available; specifically, the starting materials for preparing the compounds of the present invention, 4', 4' ' -methylenetrisphenol derivatives (i.e., compound 1), benzimidazole, 2-iodoethanol, and the like, are commercially available or can be readily prepared by known methods. The reagents used for preparing the compound are all from Keruisi chemical Co., Ltd, Tianjin, and the grade is analytical purity.
It should be further noted that: all experimental procedures were performed using Schlenk techniques and the solvents were purified by standard procedures. All reagents used for synthesis and analysis were analytically pure and were not further processed. Melting points were determined by a Boetius zone cutter.1H NRM and13the cnrm spectra were recorded by a mercury variable Vx400 spectrophotometer with measurement intervals: 400 MHz and 100 MHz. Chemical shifts, δ, were determined with reference to international standard TMS. Fluorescence spectra were determined by Cary Eclipse fluorescence spectrophotometer.
Example 1
Synthesis of Compound 2
Benzimidazole (1.122 g, 9.5 mmol) and potassium hydroxide (0.802 g, 14.3 mmol) are put into 70 mL acetonitrile solution, the temperature is gradually heated to 80 ℃, the reaction is carried out for 2 h, compound 1 (0.989 g, 1.6 mmol) dissolved in 15 mL acetonitrile is added into a reaction bottle, the reaction is continued for 3 h, the reduced pressure suction filtration is carried out, the obtained filtrate is subject to rotary evaporation to obtain white oily substance, water is added for washing, a large amount of white solid is separated out, and the white solid is collected by suction filtration to obtain compound 2.
Yield 0.900 g (78%), melting point: 151 + 153 ℃.
1H NMR (400 MHz, DMSO-d 6): δ8.24 (s, 3H, bimiH), 7.66 (q, J = 8.0 Hz, 6H, ArH), 7.23 (m, 6H, ArH), 7.66 (q, J = 8.0 Hz, 12H, ArH), 5.33 (s, 1H, CH), 4.63 (t, J = 4.4 Hz, 6H, CH 3), 4.26 (t, J = 4.8Hz, 6H, CH 3). 13C NMR (100 MHz, DMSO-d 6): δ156.1 (bimiC), 144.3 (ArC), 143.3 (ArC), 136.8 (ArC), 133.8 (ArC), 129.8 (ArC), 122.2 (ArC), 121.4 (ArC), 119.3 (ArC), 114.1 (ArC), 110.5 (ArC), 66.3 (CH2), 43.7 (CH)。
Example 2
Synthesis of Compound 3
Compound 2 (1.014 g, 1.4 mmol), 2-iodoethanol (4.814 g, 28.0 mmol) was put into 70 mL of acetonitrile solution and reacted for five days under reflux. The yellow solid precipitated after cooling to room temperature was washed three times with a small amount of acetone to give a pale yellow powdery solid. The pale yellow powder and ammonium hexafluorophosphate were dissolved in methanol, respectively, and then the whole was transferred to a 100 mL single-neck flask and stirred at room temperature for 3 days to form a yellow precipitate. Filtration and washing with ether collected a light yellow solid to give product 3.
Yield: 1.300 g (71%), melting point: 159 ℃ and 161 ℃.
1H NMR (400 MHz, DMSO-d 6): δ9.78 (s, 1H, bimiH), 8.15 (q, J = 4.0 Hz, 1H, ArH), 8.07 (q, J = 4.0 Hz, 1H, ArH), 7.69 (t, J = 4.0 Hz, 2H, ArH), 6.86 (d, J = 8.0 Hz, 2H, ArH), 6.77 (d, J = 8.0 Hz, 2H, ArH), 5.34 (s, 0.33H, CH), 5.16 (s, 1H, OH), 4.94 (t, J = 8.0 Hz, 2H, CH 2), 4.58 (t, J = 8.0 Hz, 2H, CH 2), 4.37 (t, J = 8.0 Hz, 2H, CH 2), 3.82 (s, 2H, CH 2). 13C NMR (100 MHz, DMSO-d 6): δ155.88 (ArC), 143.24 (ArC), 137.02 (ArC), 131.28 (ArC), 129.76 (ArC), 126.44 (ArC), 114.24 (ArC), 113.97 (ArC), 113.85 (ArC), 65.42 (CH2), 58.59 (CH2) , 49.00 (CH2) , 46.05 (CH)。
Application example 1
In a solution of tridentate benzimidazole salt compound in ethanol at 25 ℃ (5X 10)-6mol/L) of the same concentration of different species (15X 10)-6mol/L) TAB salt solution (F)-, Cl-, Br-, H2PO4 -, HSO4 -, OAc-And NO3 -) The fluorescence spectrum was measured and shown in FIG. 1. The results show that: compound 3 p HSO4 -Has good selective recognition capability.
Application example 2
The fluorescence titration was measured by a Cary Eclipse fluorescence spectrophotometer using a 1cm path length quartz cell. The titration was carried out by subjecting the bulk (5X 10)-6 mol L-1) Put into a 4 mL cuvette and HSO is added with increasing concentration using a microsyringe4 -Solution (0-20X 10)-6 mol L-1). The excitation wavelength of the main solution is 233 nm, and the emission spectrum has an emission peak at 337 nm. After each addition, the reaction equilibrium was reached for 8-10 minutes to determine the fluorescence intensity. Data analysis used Origin 8.0, see figure 2.
The results show that: with HSO4 -When added, the fluorescence intensity gradually increases when HSO is added4 -After adding the amount of the above-mentioned component (B), the HSO is continuously increased4 -The fluorescence intensity will not change any more.
In summary, the content of the present invention is not limited to the examples, and those skilled in the art can easily suggest other examples within the technical teaching of the present invention, but such examples are included in the scope of the present invention.
Claims (4)
1. A tridentate benzimidazole salt compound having the structure:
3。
2. the process for preparing a tridentate benzimidazole salt compound according to claim 1, which comprises the steps of:
reacting the compound 1 with benzimidazole in an organic solvent to obtain a compound 2, and reacting the compound 2 with 2-iodoethanol to obtain a compound 3; wherein the molar ratio of the compound 1 to the benzimidazole is 1: 3-1: 6; the molar ratio of the compound 2 to the 2-iodoethanol is 1: 15-1: 20;
3。
3. the preparation method according to claim 2, wherein the organic solvent in the step (A) is selected from one or more of methanol, ethanol and acetonitrile.
4. The use of compound 3 according to claim 1 as a host in the field of fluorescence recognition; wherein the fluorescence recognition system is for HSO4 -Identification of (1).
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| CN115536673A (en) * | 2022-10-26 | 2022-12-30 | 福建师范大学 | Double-ion type cyclic onium salt probe for detecting high-efficiency haloxyfop-methyl and synthetic method thereof |
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| CN115536673A (en) * | 2022-10-26 | 2022-12-30 | 福建师范大学 | Double-ion type cyclic onium salt probe for detecting high-efficiency haloxyfop-methyl and synthetic method thereof |
| CN115536673B (en) * | 2022-10-26 | 2023-12-01 | 福建师范大学 | Double-ion type cyclic onium salt probe for detecting high-efficiency haloxyfop-methyl and synthesis method thereof |
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