CN108129675B - One-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer and preparation method and application thereof - Google Patents
One-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to the field of coordination polymers, in particular to a one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer, a preparation method and application thereof; the chemical formula of the polymer is: [ Co ] A2Na2(C9H9N3O2S)4·2H2O]n·nC2H3N·nH2O, the polymer takes O-vanillin thiosemicarbazone, cobalt salt and sodium salt as raw materials, the pH value is adjusted by alkali, the polymer is synthesized by a solvent method, and crystals are obtained through self-volatilization crystallization; the complex has a one-dimensional chain structure, is simple to synthesize, convenient to purify, high in yield and good in stability in air, and compared with a sulfur-containing Schiff base ligand, the complex provided by the invention has the advantages that the antibacterial performance is obviously improved, and metal ions play a role in regulating and controlling the antibacterial activity.
Description
Technical Field
The invention relates to the field of novel biological medicine synthesis, in particular to a one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer, and a preparation method and application thereof.
Background
The Schiff base mainly refers to an imine or azomethine characteristic group compound containing carbon-nitrogen double bonds, and due to the unique physical material properties of light, electricity, magnetism and the like, good coordination chemical properties and unique physiological activities of antibiosis, anticancer, weeding and the like, the Schiff base brings about extensive theoretical and application research of people. Schiff bases and metal complexes thereof have important applications in the fields of pharmacy, catalysis, analytical chemistry, corrosion and photochromism. Schiff base has biological activities of bacteriostasis, sterilization, anti-tumor, antivirus and the like and is applied to the medical field; in the field of catalysis, cobalt and nickel complexes of Schiff bases have been applied as catalysts; the Schiff base can also be used as a good ligand, can be used for identifying and identifying metal ions and quantitatively analyzing the content of the metal ions, and has attracted extensive attention in the analysis field, in the application fields, the research on the antibiosis and bacteriostasis of the Schiff base is a hotspot of the current research, most of the researches are concentrated on simple Schiff base complexes, and the research reports on sulfur-containing heteronuclear complexes are less, so that the invention provides a one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer, and a preparation method and application thereof.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer which has a one-dimensional chain structure and good stability.
The invention also aims to provide a preparation method for preparing the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer, which has the advantages of simple operation, mild reaction conditions and high yield, and can obtain a high-purity one-dimensional chain-like structure sulfur-containing Schiff base Co-Na coordination polymer product with a uniform crystal phase.
The third purpose of the invention is to provide the application of the sulfur-containing Schiff base Co-Na coordination polymer with the one-dimensional chain structure as antibacterial activity, and the sulfur-containing Schiff base Co-Na coordination polymer has good antibacterial performance and is a good antibacterial drug.
The fourth purpose of the invention is to provide the sulfur-containing Schiff base Co-Na coordination polymer with the one-dimensional chain structure, which has the spectrum antibacterial activity and the inhibitory effect on staphylococcus aureus and escherichia coli, wherein the half inhibitory concentrations are 8.89ug/mL and 7.68ug/mL respectively.
In order to achieve the above technical objects, the present invention provides a sulfur-containing schiff base Co-Na coordination polymer having a chemical formula of formula 1:
[Co2Na2(C9H9N3O2S)4·2H2O]n·nC2H3N·nH2O
Wherein the content of the first and second substances,
C9H11N3O2structure of S
Comprises the following steps:
the structure of the repeating unit of the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer is as shown in formula 2:
the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer is a one-dimensional chain-like metal organic coordination compound formed by linking a repeating structural unit shown in a formula 2 with two adjacent Co and Na coordination compounds through an oxygen atom of o-vanillin thiosemicarbazone.
The one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer belongs to a triclinic system, and a space group is P-1; unit cell parameters:
α＝108.005(10)°,β＝92.728(10)°,γ＝93.16(10)°,
Mr＝575.97,Dc＝1.374g/cm3，Z＝2，F(000)＝592。
all data of the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer are corrected by Lp factors and empirical absorption. The crystal structure is solved by a direct method by adopting an SHELXS-97 program, the structure refinement adopts a SHELXL-97 program, and the hydrogen atoms and the non-hydrogen atoms are respectively corrected by adopting isotropic and anisotropic temperature factors by a full matrix least square method. Final deviation factor R1＝0.1087，wR2＝0.2375(w＝1/S2(F0 2)+(0.0635P)2+13.6053P]，where P＝(Fo 2+2Fc 2)/3)；(Δ/σ)max＝0.000,S＝1.128。
The unit structure of the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer is composed of 2 cobalt ions, 2 sodium ions, 4 o-vanillin thiosemicarbazone molecules, 2 water molecules and 1 acetonitrile molecule. The cobalt (III) ion coordinates 2 oxygen atoms, 2 nitrogen atoms and 2 sulfur atoms from 2 o-vanillin thiosemicarbazone molecules, and is in a coordination environment of a hexa-coordinated distorted octahedron. The sulfur-containing Schiff base Co-Na coordination polymer with the one-dimensional chain structure has a stable molecular structure, and due to the strong stability of the structure of the polymer, the phenomena of decomposition, breakage, melting and the like are not easy to occur in the antibacterial experiment process, and meanwhile, a sulfur atom on a ligand is easy to form a bridging complex, so that the activity of active species of the coordination polymer is increased, and the spectrum antibacterial activity is improved.
The invention provides a preparation method of a one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer, which comprises the steps of dissolving cobalt salt, sodium salt and o-vanillin thiosemicarbazone in a mixed solvent according to a molar ratio of (1-3) to (2-7) to (1-4), reacting for 3-6 hours, adjusting the pH value to 5-8 by using alkali, reacting for 7-18 hours at 50-110 ℃, cooling to room temperature, filtering, and performing self-volatilization crystallization on the obtained filtrate at room temperature to obtain the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer.
The preparation method of the one-dimensional chain sulfur Schiff base Co-Na coordination polymer further comprises the following preferable scheme:
preferably, the cobalt salt comprises at least one of cobalt nitrate, cobalt chloride, cobalt sulfate, cobalt carbonate, cobalt perchlorate, cobalt acetate and basic cobalt carbonate.
In a preferred embodiment, the sodium salt includes at least one of sodium chloride, sodium sulfate, sodium carbonate, cobalt nitrate, sodium bicarbonate, sodium acetate, and sodium perchlorate.
In a preferred scheme, the mixed solvent is mainly a mixture of solvents with different dissolving polarities and different volatilities; the mixed solvent comprises two of methanol, ethanol, trichloromethane, dichloromethane and acetonitrile, and at least one of N, N '-dimethylformamide, N' -dimethylacetamide and water in a volume ratio of 1-3: 5-20: 1-5.
In a preferred scheme, the mixed solvent is methanol, and the combination of N, N' -dimethylformamide and acetonitrile; ethanol, N' -dimethylformamide and acetonitrile in combination; methanol, acetonitrile and N, N' -dimethylformamide in combination; tetrahydrofuran, methanol and N, N' -dimethylacetamide in combination; tetrahydrofuran, ethanol in combination with N, N '-dimethylformamide or in combination with N, N' -dimethylacetamide.
In the preferable scheme, at least one of sodium hydroxide, potassium hydroxide, ammonia water, triethylamine, diethylamine and triethanolamine is adopted to adjust the pH value.
In the preferred scheme, the self-volatilization crystallization is to contain the filtrate in an open container, seal the opening of the container by a preservative film with holes and volatilize the solvent at room temperature until crystals are separated out.
The preservative film is a conventional commercial preservative film.
The invention also provides an application of the one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer, wherein the application of the one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer as an antibacterial agent has a good inhibition effect on staphylococcus aureus and escherichia coli.
In a preferable scheme, the one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer is applied to the antibacterial activity on staphylococcus aureus and escherichia coli.
The invention also provides application of the one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer, and the one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer is applied as a luminescent material.
The invention has the beneficial effects that: 1) the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer has a one-dimensional chain structure by taking o-vanillin thiosemicarbazone as a ligand, and the molecular structure stability of the coordination polymer is good.
2) The one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer has good luminescence performance, can be widely applied to preparation of luminescent devices as a luminescent material, and widens the selection range of the luminescent material.
3) The one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer also has good antibacterial performance, and has good inhibition effect when being applied to antibacterial activity research of staphylococcus aureus and escherichia coli.
4) The preparation method of the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer has the advantages of simple operation, mild reaction conditions, high yield of the obtained product and uniform crystal particles.
Drawings
FIG. 1 is an infrared spectrum of a one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer crystal prepared by the invention;
FIG. 2 is a schematic structural diagram of a one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer structural unit prepared by the invention;
FIG. 3 is a one-dimensional chain diagram of a one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer adopted in the present invention;
FIG. 4 is a fluorescence emission spectrogram of a one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer crystal prepared by the invention.
Detailed Description
The following examples are intended to further illustrate the content of the invention, but not to limit the scope of the invention.
Dissolving cobalt salt, sodium salt and o-vanillin thiosemicarbazone in a mixed solvent, wherein the molar ratio of the cobalt salt, the sodium salt and the o-vanillin thiosemicarbazone is 1-3: 2-7: 1-4, heating in a water bath, carrying out reflux reaction for 3-6 hours, adjusting the pH value to 5-8 by using alkali, continuing heating and stirring, reacting for 7-18 hours at 50-110 ℃, cooling to room temperature, filtering, and carrying out self-volatilization crystallization on the obtained filtrate at room temperature.
The first embodiment is as follows:
the synthesis of one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer comprises the following reaction steps:
0.80mmol (180.22mg) of o-vanillin thiosemicarbazone, 0.80mmol (about 232.84mg) of cobalt nitrate hexahydrate and 0.8mmol (84.79mg) of sodium carbonate are sequentially added into a mixed solvent of 24mL of N, N' -dimethylacetamide, acetonitrile and methanol (the volume ratio is 2:5:3), the mixture is heated and refluxed for 4h in a water bath, the pH value is adjusted to 5-7 by potassium hydroxide, the mixture is continuously heated and stirred, the temperature is controlled to be about 50-65 ℃, the reaction lasts for 18h to obtain a red solution, and the red solution is filtered, sealed and naturally volatilized at room temperature, red crystals suitable for X-ray single crystal structure analysis are separated after three weeks, and the yield is 52.36%. M.P.291-293 ℃; fig. 1 shows that the IR major absorption peaks are: 3255(w), 3443(m), 3280(m), 2922(w), 2824(w), 1579(vs), 1488(vs), 1436(vs), 1292(s), 1217(s), 1139(m), 1104(m), 967(m), 855(w), 735(m), 598(w), 540(w), 479(w), 428 (w). Elemental analysis C19H22.5CoN6.5NaO5.5S2Calculated (%), C39.62, H3.94, N15.81; found (%), C39.50, H3.93 and N15.87. C.
Example two:
synthesizing a one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer:
0.48mmol (108.13mg) of o-vanillin thiosemicarbazone, 0.52mmol (129.52mg) of cobalt acetate tetrahydrate and 0.72mmol (42.08mg) of sodium chloride are sequentially added into a mixed solvent of 20mLN, N' -dimethylacetamide, acetonitrile and ethanol (the volume ratio is 4:12:7), the mixture is heated and refluxed in a water bath for 3 hours, the pH value is adjusted to 6-7 by triethylamine, the mixture is continuously heated and stirred, the temperature is controlled to be 65-80 ℃, the mixture is reacted for 19 hours to obtain a red solution, and the red solution is filtered, sealed and naturally volatilized at room temperature, red crystals suitable for X-ray single crystal structure analysis are separated after 20 days, and the yield is 46.26%.
Example three:
synthesizing a one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer:
0.64mmol (144.17mg) of o-vanillin thiosemicarbazone, 0.72mmol (202.50mg) of cobaltous sulfate heptahydrate and 0.72mmol (60.49mg) of sodium bicarbonate are sequentially added into a mixed solvent of 20mL of N, N' -dimethylformamide, acetonitrile and methanol (the volume ratio is 5:15:8), the mixture is heated and refluxed for 5h in a water bath, the pH value is adjusted to 6-7 by triethanolamine, the mixture is continuously heated and stirred, the temperature is controlled to be 55-70 ℃, the mixture is reacted for 16 h to obtain a red solution, and the red solution is filtered, sealed and naturally volatilized at room temperature, red crystals suitable for X-ray single crystal structure analysis are separated after three weeks, and the yield is 50.23%.
Example four:
for the Schiff base Co-Na coordination polymer [ Co ] prepared in the embodiment 1-32Na2(C9H11N3O2S)4·H2O]n·C2H3N·2H2And carrying out structural determination on the O crystal.
Under microscope, single crystal of size 0.25mm × 0.22.22 mm × 0.20.20 was selected, and diffraction experiments were performed on a Bruker APEX-IICCD single crystal diffractometer using MoK α radiation (λ 0.071073nm) at 296(2) K
The scanning mode collects 9479 diffraction points and 5577 independent diffraction points [ R ] in the range of 2.12-25.00 DEGint＝0.0779,Rsigma＝0.0645]3964 observable diffraction points [ I>2σ(I)]For structural analysis and structural correction. All data were corrected for Lp factor and empirical absorption. The crystal structure is solved by a direct method by adopting an SHELXS-97 program, the structure refinement adopts a SHELXL-97 program, and the hydrogen atoms and the non-hydrogen atoms are respectively corrected by adopting isotropic and anisotropic temperature factors by a full matrix least square method. Final deviation factor R1＝0.1087，wR2＝0.2375(w＝1/S2(F0 2)+(0.0635P)2+13.6053P],where P＝(Fo 2+2Fc 2)/3)；(Δ/σ)max＝0.000,S＝1.128,(Δρ)max＝1.173and
The structure of the coordination polymer structural unit is shown in FIG. 2, the main bond lengths and bond angles are shown in Table 1, and the one-dimensional chain structure of the coordination polymer is shown in FIG. 3. As can be seen from FIG. 2, the coordination polymer building block consists of 1 cobalt (III) ion, 2 o-vanillin thiosemicarbazone molecules, 1 sodium ion, 1 coordinated water molecule, 1 free water molecule and 1 acetonitrile molecule. The cobalt (III) ion coordinates 2 oxygen atoms, 2 nitrogen atoms and 2 sulfur atoms from 2 o-vanillin thiosemicarbazone molecules. Formation of CoN2O2S2A distorted octahedral structure. Na (I) coordinates with 3 oxygen atoms, 1 nitrogen atom and 1 oxygen atom in coordinated water from the ortho-vanillin thiosemicarbazone molecule to form NaO4N1The structure of the deformed square pyramid. As can be seen from FIG. 3 and Table 1, the whole molecule forms a one-dimensional chain structure, two adjacent cobalt ions, two sodium ions and four adjacent vanillin thiosemicarbazone molecules form a 10-membered ring structure, and the distances between the adjacent Co-Co and Na-Na are 7.036 and 7.036 respectively
The bond lengths of Co-N (1) and Co-N (4) are 1.903 and
the bond lengths of Co-O (2) and Co-O (4) were 1.950 and
the bond lengths of Co-S (1) and Co-S (4) are 2.215 and
they are all within the normal range. The distance between the atoms bound to sodium being relatively large, Na-N (5) being
Bond length of Na-O is in
And (3) a range.
TABLE 1 major bond length of the complexes
Angle of and key (°)
Example five:
the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer prepared in the embodiment 1-3 has the following luminescent properties:
the fluorescence property of the material is measured, and the result shows that: (1) measuring the solid fluorescence spectrum of the complex at room temperature, and measuring the solid fluorescence emission spectrogram of the material under the excitation of 280-430 nm ultraviolet light (see figure 4); (2) as can be seen from FIG. 4, the emission spectrum of the complex was 429nm (. lamda.)ex376nm) due to a transition between pi-pi and the emission spectrum 389nm (lambda) from the emission spectrum of the free ligand o-vanillin thiosemicarbazoneex300nm) was red-shifted by 40nm, attributable to the interaction between the ligand and the metal ion in the complex; (3) emission light enhancementAs a result of the charge transfer from the ligand to the metal ion, a better fluorescent material is obtained due to the high stability and poor solubility of the complex.
Example six:
one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer [ Co ] prepared in example 1 to 32Na2(C9H9N3O2S)4·H2O]n·C2H3N·2H2Antibacterial activity of O:
the experimental method comprises respectively diluting the strains of cultured Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli into 2 × 104each/mL of the cells were dispensed into a 96-well plate of 0.1 mL/well and 10. mu.L/well, incubated at 37 ℃ in a constant temperature incubator for 24 hours, added with 5mg/mL of MTT solution 40. mu.L/well, and incubated for 4 hours. The plates were removed, centrifuged, the supernatant was decanted, DMSO was added at 150. mu.L/well, OD was measured at 570nm using a BioRad550 microplate reader from America, and the median inhibitory concentrations of the different sulfur-containing Schiff base metal complexes were calculated, with penicillin and streptomycin as positive controls (see Table 2). Because the synthesized Schiff base contains sulfur atoms, the antibacterial activity of the Schiff base is higher than that of other general Schiff base metal complexes.
TABLE 2 results of the test of bacteriostatic activity of the materials, complexes and control groups
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (10)
1. A one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer is characterized in that: the chemical formula of the polymer is:
[Co2Na2(C9H9N3O2S)4·2H2O]n·nC2H3N·nH2O
wherein the content of the first and second substances,
C9H11N3O2the structure of S is as follows:
the structure of a repeating unit of the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer is as follows:
2. the one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer as claimed in claim 1, wherein the one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer belongs to a triclinic system, and the space group is P-1; unit cell parameters:
α＝108.005(10)°，β＝92.728(10)°，γ＝93.16(10)°，
Mr＝575.97，Dc＝1.374g/cm3，Z＝2，F(000)＝592。
3. the preparation method of the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer as claimed in any one of claims 1 to 2, characterized in that a cobalt salt, a sodium salt and o-vanillin thiosemicarbazone are dissolved in a mixed solvent, the molar ratio of the cobalt salt, the sodium salt and the o-vanillin thiosemicarbazone is 1-3: 2-7: 1-4, after reaction for 3-6 h, the pH value is adjusted to 5-8 by using an alkali, heating is continued for 7-18 h, the temperature is controlled to be 50-110 ℃, cooling is carried out to room temperature, filtering is carried out, and the obtained filtrate is crystallized by self-volatilization at room temperature.
4. The method for preparing a one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer according to claim 3, wherein the cobalt salt comprises at least one of cobalt nitrate, cobalt chloride, cobalt sulfate, cobalt carbonate, cobalt perchlorate, basic cobalt carbonate and cobalt acetate.
5. The method for preparing a one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer according to claim 3, wherein the sodium salt comprises at least one of sodium chloride, sodium sulfate, sodium carbonate, sodium nitrate, sodium bicarbonate, sodium perchlorate and sodium acetate.
6. The preparation method of the one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer according to claim 3, wherein the mixed solvent comprises any two of methanol, ethanol, chloroform, tetrahydrofuran, dichloromethane and acetonitrile, and any one of N, N '-dimethylformamide, N' -dimethylacetamide and water in a volume ratio of 1-3: 5-20: 1-5.
7. The method for preparing a one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer according to claim 3, wherein at least one of sodium hydroxide, potassium hydroxide, ammonia water, triethylamine, diethylamine and triethanolamine is used for adjusting the pH value.
8. The method for preparing a one-dimensional chain-like sulfur-containing Schiff base Co-Na coordination polymer as claimed in claim 3, wherein the self-volatilization crystallization is carried out by putting the filtrate in an open container, closing the opening of the container with a perforated preservative film, and volatilizing the solvent at room temperature until crystals are precipitated.
9. Use of a one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer according to any one of claims 1 to 2, for antibacterial purposes.
10. Use of a one-dimensional chain sulfur-containing Schiff base Co-Na coordination polymer according to any one of claims 1 to 2, as a light-emitting material.
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