CN107794036A - The synthesis and application for the metal organic framework compound constructed based on the dicarboxylic acids of thiophene 2,5 and 4,4 ' bipyridyls - Google Patents
The synthesis and application for the metal organic framework compound constructed based on the dicarboxylic acids of thiophene 2,5 and 4,4 ' bipyridyls Download PDFInfo
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Abstract
The invention discloses a kind of synthesis and application of the metal organic framework compound constructed based on the dicarboxylic acids of thiophene 2,5 and 4,4 ' bipyridyls.The compound chemical formula being related to is [C16H10CuN2O4S]n, crystal belongs to monoclinic system, P21/c space groups, cell parameter a=8.258, b=10.5015, c=11.1725, α=89.740 °, β=75.477 °, γ=83.629 °, volume V=931.9 3 of structure cell, center of area structure cell F (000)=394, GOOF=1.903, molecular number Z=2 in structure cell.With the dicarboxylic acids of thiophene 2,5,4,4 ' bipyridyls and mantoquita for raw material, reacted 72 hours at 140 DEG C, be cooled to room temperature.The present invention is simple to operate, and green, products therefrom can be used as fluorescence probe, applied to analysis detection field.
Description
Technical field
It is [C the present invention relates to a kind of chemical formula16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4,4 '-bipyridyl
The synthesis and application for the metal organic framework compound constructed.
Background technology
Metal organic frame (Metal-Organic Frameworks, MOFs) material as new functional, because
It has larger specific surface area, neat porous structure, selects adsorption capacity, persistent micropore, preferable chemically stable
Property, duct is inside and outside to have the advantages of functional group that can be modified and enrich etc. is a series of prominent and characteristic, is obtained in many fields
To being widely applied, there is preferable DEVELOPMENT PROSPECT to exist, in analytical chemistry field, MOFs materials also turn into popular topic it
One.
Application of the MOFs materials in adsorbing separation：Adsorbing separation is that most possibly realization is applied to industrial neck to MOFs materials
The performance in one of domain, and one of field of MOFs material properties that research is most extensive at present, development is most.With regard to current research
As a result show, MOFs materials are shown excellent performance in terms of gas-liquid phase separation, actually should due to its special structure
There is good prospect in.Yang Shu et al. Y (NO3)3·6H2O and 1, the Y (BTC) of 3,5- trimesic acids (BTC) synthesis
(H2O)6There is higher selection performance to hemoglobin, and this performance complies fully with La Miaoer equation models.
Application of the MOFs materials in chromatography：At present, MOFs materials are used for major part among chromatography all
It is chiral, it has big specific surface area, and the high-sequential of pore structure, chemical property is stable and chiral microenvironment is special waits spy
Point, and chromatography just needs the material with these features to be operated.Again, chiral MOFs is because it contains chirality
Functional group is with chiral hole and with chiral function, absorption that can be by chiral functional group or chiral cavity and selectivity
Recognition reaction is used for the fractionation of chipal compounds.With to its in-depth study, the chiral Recognition site of chiral MOFs materials and
Package assembly is more and clearer and more definite, is directed to the outstanding design that different chipal compounds are readily isolated, therefore in enantiomer side
Face also has good application advantage.
2007, build etc. and to report a kind of chiral MOF materials [Zn2(D-Cam)2(4,4 '-pydc)]n, its composition
In contain homogeneous chiral lamella, be made up of pyridine ligand column, be two kinds of special six connection from interspersed knot
Structure, its homogeneous chiral lamella are formed by left hand, the arrangement of right-handed helix chain rule. [Zn2(D-Cam)2(4,4 '-pydc)]nIt is brilliant
The unique texture of body, reacts under certain condition, the energy crystal that directly synthesis particle is moderate, shape is relatively uniform, i.e., very suitable
Close and be applied to the chiral separation of colleges and universities' chromatogram.Application of the MOFs materials in quantitative chemical analysis：By means of chromatogram, fluorescence side
Method, quantitative chemical analysis can be done among MOFs materials applications to the detection to Cucumber.Such as detect, differentiate it is some
Metal ion, and the MOFs materials with pore passage structure, make it be widely used in mesoporous suction-operated.
The content of the invention
It is [C it is an object of the invention to provide a kind of chemical formula16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4,
The synthesis and application for the metal organic framework compound that 4 '-bipyridyl is constructed.
Chemical formula is [C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4, metal organic frame that 4 '-bipyridyl is constructed
Compound crystal belongs to monoclinic system, and P21/c space groups, cell parameter
α=89.740 °, β=75.477 °, γ=83.629 °, the volume of structure cellCenter of area structure cell F (000)=394,
GOOF=1.903, molecular number Z=2 in structure cell, actual crystal numerical value are shown in Table 1, and part bond distance's bond angle is shown in Table 2.Chemical formula is
[C16H10CuN2O4S]nBased on thiophene -2,5- dicarboxylic acids and 4, metal organic framework compound that 4 '-bipyridyl is constructed have compared with
Strong fluorescence intensity, fluorescence probe can be used as to be applied to analysis detection field.
Table 1：Chemical formula is [C16H10CuN2O4S] n metal organic framework compound crystallographic parameters
Table 2：Chemical formula is [C16H10CuN2O4S]nThe main bond distance of metal organic framework compoundBond angle (°)
| Cu1-O4 | 1.954(9) | C15-H15 | 0.930(1) | Cu1-N1 | 1.966(11) |
| C13-C12 | 1.39(2) | Cu1-O2 | 1.979(11) | C13-H13 | 0.930(1) |
| Cu1-N2 | 2.086(11) | C9-C10 | 1.28(3) | Cu1-O3 | 2.261(13) |
| C9-C8 | 1.30(3) | S1-C1 | 1.708(19) | C5-C4 | 1.54(2) |
| S1-C4 | 1.723(15) | C12-H12 | 0.930(1) | O4-C5 | 1.256(19) |
| C8-H8 | 0.930(1) | C7-N2 | 1.34(2) | C6-O1 | 1.24(2) |
| O4-Cu1-N1 | 90.7(4) | O3-C5-O4 | 128.1(14) | O4-Cu1-O2 | 157.6(5) |
| O3-C5-C4 | 118.4(14) | N1-Cu1-O2 | 87.9(4) | O4-C5-C4 | 113.5(14) |
| O4-Cu1-N2 | 89.1(4) | N1-C12-C13 | 124.9(15) | N1-Cu1-N2 | 178.0(5) |
| N1-C12-H12 | 117.6(1) | O2-Cu1-N2 | 93.1(4) | C13-C12-H12 | 117.6(1) |
| O2-Cu1-N2 | 93.1(4) | C13-C12-H12 | 117.6(1) | O4-Cu1-O3 | 115.8(5) |
| C9-C8-C7 | 122(2) | N1-Cu1-O3 | 91.4(5) | C9-C8-H8 | 118.8(1) |
| O2-Cu1-O3 | 86.5(5) | C7-C8-H8 | 118.8(1) | N2-Cu1-O3 | 86.9(5) |
| O1-C6-O2 | 125.0(17) | C1-S1-C4 | 90.8(8) | O1-C6-C1 | 120.0(18) |
Described chemical formula is [C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4, gold that 4 '-bipyridyl is constructed
Category organic frame compound synthesis concretely comprises the following steps：
(1) 15mL is contained to 0.5mmol (0.0725g) Cu (NO3)3·3H2O, 0.5mmol (0.0861g) thiophene-
The 4 of 2,5- dicarboxylic acids (2,5-tdc) and 0.5mmol (0.0781g), the distilled water solution of 4 '-bipyridyl (4,4 '-pydc), then
4mL absolute methanols (CH is added toward it3OH) magnetic agitation 1 hour at room temperature, homogeneous mixture solotion is obtained；
(2) homogeneous mixture solotion obtained by step (1) is placed in hydrothermal reaction kettles of the 25mL with polytetrafluoroethylsubstrate substrate,
Reactor is put into baking oven, 140 DEG C of then crystallization 72 hours is heated to, then enters line program cooling, cool 10 DEG C per hour
To 100 DEG C, then 10 hours are incubated, turn off after baking oven is cooled to room temperature in its natural state by it and take out reactor, there is blue pin
Shape crystal generates, and filtering, then dries at room temperature, collects sample, it is [C to obtain chemical formula16H10CuN2O4S]nBased on thiophene -2,
5- dicarboxylic acids and 4, the metal organic framework compound that 4 '-bipyridyl is constructed.
Chemical formula is [C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4, the metal that 4 '-bipyridyl is constructed is organic
Framework compound can be used as fluorescence probe, applied to analysis detection field.
The inventive method is simple to operate, green, and products therefrom has stronger photoluminescent property, can be in analysis detection field
As fluorescence probe.
Brief description of the drawings
Fig. 1 is that chemical formula is [C in the embodiment of the present invention16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4,4 '-
The metal organic framework compound construction unit figure that bipyridyl is constructed.
Fig. 2 is that chemical formula is [C in the embodiment of the present invention16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4,4 '-
The metal organic framework compound coordination polyhedrom figure that bipyridyl is constructed.
Fig. 3 is that chemical formula is [C in the embodiment of the present invention16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4,4 '-
The metal organic framework compound crystal three-dimensional accumulation graph (a directions) that bipyridyl is constructed.
Fig. 4 is that chemical formula is [C in the embodiment of the present invention16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4,4 '-
The metal organic framework compound fluorescence spectrum that bipyridyl is constructed, wherein：The transmitting of a- 2,5-ThiophenedicarboxyliAcid Acid parts and excite
Spectrum；B-MOFs launches and excitation spectrum.
Embodiment
Embodiment：
(1) 15mL is contained to 0.5mmol (0.0725g) Cu (NO3)3·3H2O, 0.5mmol (0.0861g) thiophene-
The 4 of 2,5- dicarboxylic acids (2,5-tdc) and 0.5mmol (0.0781g), the distilled water solution of 4 '-bipyridyl (4,4 '-pydc), then
4mL absolute methanols (CH is added toward it3OH) magnetic agitation 1 hour at room temperature, homogeneous mixture solotion is obtained.
(2) homogeneous mixture solotion obtained by step (1) is placed in hydrothermal reaction kettles of the 25mL with polytetrafluoroethylsubstrate substrate,
Reactor is put into baking oven, 140 DEG C of then crystallization 72 hours is heated to, then enters line program cooling, cool 10 DEG C per hour
To 100 DEG C, then 10 hours are incubated, turn off after baking oven is cooled to room temperature in its natural state by it and take out reactor, there is blue pin
Shape crystal generates, and filtering, then dries at room temperature, collects sample, it is [C to obtain chemical formula16H10CuN2O4S]nBased on thiophene -2,
5- dicarboxylic acids and 4, the metal organic framework compound that 4 '-bipyridyl is constructed, its yield 72%, elementary analysis result：Theoretical value
(%)：C, 56.18；H, 3.38；Test value (%)：C, 56.03；H, 3.44.
Gained chemical formula is [C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4, metal that 4 '-bipyridyl is constructed
Organic frame compound is as fluorescence probe, applied to analysis detection field.
The chemical formula of acquisition is [C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4, gold that 4 '-bipyridyl is constructed
Belong to organic frame compound and carry out crystal structure determination.Assay method is：It is 0.33 × 0.28 × 0.13mm brilliant to choose size
Body, with Bruker SMART APEX CCD single crystal diffractometers, collect crystal data.Using through graphite monochromatised Mo-K alpha rays
(γ=0.071073nm), useScan pattern, point diffraction is collected in 293 (2) K in the range of 3.3 ° -29.1 °.Diffraction
Intensity data carries out empirical absorption correction with SADABS programs.The structure of crystal is parsed with SHELXS-97 programs by direct method
Out, complete matrix least square is carried out with SHELXS-97 programs to the coordinate and its anisotropic parameters of whole non-hydrogen atoms
Method amendment.All hydrogen atoms are all to be hydrogenated with theory.
Analytical chemistry formula is [C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4, metal that 4 '-bipyridyl is constructed
Organic frame compound crystal structure shows, it is monoclinic system, and P21/c space groups, cell parameterα=89.740 °, β=75.477 °, γ=83.629 °, structure cell
Volume V=931.93, center of area structure cell F (000)=394, GOOF=1.903, molecular number Z=2 in structure cell, actual crystal numerical value
It is shown in Table 1, it is construction unit figure that part bond distance's bond angle, which is shown in Table 2, Fig. 1, and the coordination polyhedrom figure of metallic atom, Fig. 3 are centered on Fig. 2
[C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4, the metal organic framework compound that 4 '-bipyridyl is constructed is in a side
Upward accumulation graph.As shown in Table 1, the empirical formula for being tested metal organic framework compound is C34H36N6Co2O16, by Fig. 1 and Fig. 2
Understand, each cobalt ions is combined with two nitrogen-atoms and four oxygen atoms, and the ligancy of cobalt ions is 6, passes through connection
Oxygen atom and nitrogen-atoms form the Binuclear Cobalt of hexahedron symmetrical configurations.The cobalt ions coordination ring of tested metal organic framework compound
Border such as Fig. 2, in the coordination environment of center cobalt ions 1, the carboxyl oxygen atom of O1 and O5 in pyridine -2,5- dicarboxylic acids, O1
With oxygen atoms of the O5 among solvent, while N11, N14 be respectively from main part pyridine -2,5- dicarboxylic acids, assistant ligand 4,
Nitrogen-atoms on 4 '-bipyridyl；Nitrogen-atoms, auxiliary on the next autonomous part pyridine of coordination atom N16, N19 of center cobalt ions 2
Part 4, the nitrogen-atoms on 4 '-bipyridyl, O2 come from the carboxyl oxygen atom in pyridine -2,5- dicarboxylic acids, and O4, O8, O10 carry out self-dissolving
Oxygen atom among agent.As shown in Table 2, Co-O coordinate bond is up toIt is most short to beCo-N coordination
Key is up toIt is most short to beChemical formula is [C34H36N6Co2O16] n is based on thiophene -2,5- dicarboxylic acids and 4,
The metal organic framework compound that 4 '-bipyridyl is constructed has 1D duct (Fig. 3), pore size 0.898 along a direction of principal axis
×0.816nm2。
Fig. 4 is [C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4, metal organic frame that 4 '-bipyridyl is constructed
Compound fluorescence emission spectrum (excitation wavelength 402nm) and excitation spectrum.As can be seen from Figure 4, [C16H10CuN2O4S]nBased on thiophene
Fen -2,5- dicarboxylic acids and 4, the metal organic framework compound maximum emission peak that 4 '-bipyridyl is constructed are located at λEm=469nm, with
Part is compared, launch wavelength red shift, bands of a spectrum shape, intensity enhancing.After part forms complex, launch wavelength red shift, it is due to
Part forms MOFs structures, rigidity and the enhancing of copline degree with ion, conjugated system is increased, so as to cause launch wavelength red
Move, there is more electronics to return to ground state, cause fluorescence intensity to strengthen.
Claims (3)
1. a kind of chemical formula is [C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4, the metal that 4 '-bipyridyl is constructed is organic
Framework compound, it is characterised in that chemical formula is [C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4,4 '-bipyridyl structure
The metal organic framework compound crystal built belongs to monoclinic system, and P21/c space groups, cell parameterα=89.740 °, β=75.477 °, γ=83.629 °, the body of structure cell
ProductCenter of area structure cell F (000)=394, GOOF=1.903, molecular number Z=2 in structure cell, actual crystal numerical value
1 is shown in Table, part bond distance's bond angle is shown in Table 2；Chemical formula is [C16H10CuN2O4S]nMetal organic framework compound has stronger glimmering
Luminous intensity, fluorescence probe can be used as to be applied to analysis detection field；
Table 1：Chemical formula is [C16H10CuN2O4S] n metal organic framework compound crystallographic parameters
Table 2：Chemical formula is [C16H10CuN2O4S]nThe main bond distance of metal organic framework compoundBond angle (°)
2. chemical formula according to claim 1 is [C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4,4 '-connection pyrrole
The metal organic framework compound synthetic method that pyridine is constructed, it is characterised in that concretely comprise the following steps：
(1) 15mL is contained to 0.0725g Cu (NO3)3·3H2O, 0.0861g 2,5-ThiophenedicarboxyliAcid Acid (2,5-tdc) and
The 4 of 0.0781g, the distilled water solution of 4 '-bipyridyl (4,4 '-pydc), then add 4mL absolute methanols, at room temperature magnetic toward it
Power stirs 1 hour, obtains homogeneous mixture solotion；
(2) homogeneous mixture solotion obtained by step (1) is placed in hydrothermal reaction kettles of the 25mL with polytetrafluoroethylsubstrate substrate, will be anti-
Answer kettle to be put into baking oven, be heated to 140 DEG C of then crystallization 72 hours, then enter line program cooling, cool 10 DEG C to 100 per hour
DEG C, then 10 hours are incubated, turn off after baking oven is cooled to room temperature in its natural state by it and take out reactor, there is blue acicular crystal
Generation, filtering, is then dried at room temperature, collects sample, it is [C to obtain chemical formula16H10CuN2O4S]nBased on thiophene -2,5- dicarboxyl
Acid and 4, the metal organic framework compound that 4 '-bipyridyl is constructed.
3. chemical formula according to claim 1 is [C16H10CuN2O4S]nBased on 2,5-ThiophenedicarboxyliAcid Acid and 4,4 '-connection pyrrole
The application for the metal organic framework compound that pyridine is constructed, it is characterised in that chemical formula is [C16H10CuN2O4S]nBased on thiophene -2,
5- dicarboxylic acids and 4, the metal organic framework compound that 4 '-bipyridyl is constructed can be used as fluorescence probe, applied to analysis detection neck
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| CN110551293A (en) * | 2019-09-19 | 2019-12-10 | 桂林理工大学 | 3, 4-ethylenedioxy group thiophene-2, 5-dicarboxylic acid zinc complex and preparation method thereof |
| CN110615803A (en) * | 2019-09-19 | 2019-12-27 | 桂林理工大学 | 3, 4-ethylenedioxy group thiophene-2, 5-dicarboxylic acid copper complex and preparation method thereof |
| CN112409249A (en) * | 2020-10-28 | 2021-02-26 | 桂林理工大学 | 6-methylpyridine-2, 3-dicarboxylic acid zinc complex and preparation method thereof |
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