CN105061518A - Metal-organic coordination polymer with mixed ligand and preparation method of metal-organic coordination polymer - Google Patents

Metal-organic coordination polymer with mixed ligand and preparation method of metal-organic coordination polymer Download PDF

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CN105061518A
CN105061518A CN201510511954.3A CN201510511954A CN105061518A CN 105061518 A CN105061518 A CN 105061518A CN 201510511954 A CN201510511954 A CN 201510511954A CN 105061518 A CN105061518 A CN 105061518A
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transition
metal
preparation
polymkeric substance
coordination polymer
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汪永涛
王翠翠
王金华
汤桂梅
万文珠
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Qilu University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/02—Iron compounds
    • C07F15/025—Iron compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic System without C-Metal linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic System
    • C07F13/005—Compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/04—Nickel compounds
    • C07F15/045—Nickel compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/06—Cobalt compounds
    • C07F15/065—Cobalt compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic System without C-Metal linkages

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Abstract

The invention provides a synthetic method and structural characterization of a transition metal coordination polymer. The transition metal coordination polymer has the molecular formula of [M(L)(4PBI)(H2O)]n, wherein L is 4-(1-carboxyethyl)benzoic acid; 4PBI is 2-(pyridine-4yl)benzimidazole; M is a transition metal ion at the fourth period in the periodic table of elements. The transition metal complex is prepared in such a way that L, 4PBI and metal salts are mixed and dissolved in water according to a certain proportion, then a certain quantity of sodium hydroxide is added, the mixture is placed in a polytetrafluoroethylene tube to be sealed, the polytetrafluoroethylene tube is placed in a stainless steel reaction kettle, the reaction kettle is placed in a GZX-9030 MBE electrothermal blower, crystallization is performed for 0.1-7 days at 50-200 DEG C, the room temperature is obtained through natural cooling, granular crystals are separated, and the productivity can be 50% or above. The coordination polymer with the mixed ligand is easy to prepare, good in stability and high in crystallinity, and has a very good potential application prospect in the field of biological activity, molecular magnets, molecular luminescence and the like.

Description

A kind of metal organic coordination polymer with mixed ligand and preparation method thereof
Technical field
The invention belongs to the synthesis field of metal organic coordination polymer, relate to a kind of metal organic coordination polymer with mixed ligand and preparation method thereof.
Background technology
The one dimension that ligand polymer is mainly obtained by the organic ligand containing nitrogen, oxygen and metal ion generation coordination reaction, the compound of two and three dimensions.In order to obtain various interesting topological framework, recent people utilize two kinds or two or more different ligands to construct supramolecular network structure in the process of self-assembly.Wherein, nitrogen heterocyclic ring-organic carboxyl acid class mixed ligand is mixed ligand more common at present.
In recent years, the coordination mode various due to carbon containing heterocyclic carboxylic acid and the nitrogen-atoms of containing n-donor ligand and the strong coordination ability of transition metal, the favor of organic carboxyl acid-nitrogen-containing hetero lopps mixed ligand extremely chemist when synthesizing ligand polymer.The feature that carbon containing heterocyclic carboxylic acid class part has: can partly or entirely deprotonation under (1) different pH value, produces coordination multi-form, in various degree with metal center, simultaneously can as hydrogen bond receptor and donor.(2) its bending skeleton and various coordination mode become and build multi-link coordination compound and well select.To transition metal, there is stronger coordination ability due to the nitrogen-atoms in nitrogenous class part and nitrogen-containing hetero lopps ligand polymer has the character such as optical, electrical and magnetic, and be widely used in synthesis and the research of transition metal complex.Nitrogenous class part of a great variety, wherein, imidazoles and pyridines are two the most frequently used classes.Angle between the hapto of containing n-donor ligand, spacing and hard and soft can affect the coordination mode of carboxylic acid, and then form different secondary structure units, thus form various structure.By above feature, they have very large synergistic effect when participating in coordination, the centrosymmetric title complex of easy formation, and coordination ability when nitrogen-atoms and carboxyl and metallic ion coordination is different with selectivity, often can obtain the ligand polymer of various structures novelty, excellent performance.(Z.Y.Li,Z.M.Zhang,J.W.Dai,[J].J.Mol.Struct.,2010,963,50-56；S.Y.Zhang,Z.J.Zhang,W.Shi,B.ZhaoP.Cheng,[J].InorganicaChimicaActa.,2010,363,3784-3789)。
Summary of the invention
The invention provides a kind of metal organic coordination polymer with mixed ligand and preparation method thereof.
The invention provides a kind of transition-metal coordination polymkeric substance, molecular formula is: [M (L) (4PBI) (H 2o)] nwherein for L is 4-(1-propyloic) phenylformic acid, 4PBI is 2-(pyridine-4 base) benzoglyoxaline, and M is the transition metal ion of periodic table of elements period 4.
The metal organic coordination polymer with mixed ligand provided by the invention mainly takes following technical scheme: mix soluble in water by L and 4PBI and metal-salt with a certain proportion of amount of substance, add a certain amount of sodium hydroxide, be placed in polyfluortetraethylene pipe to seal, put in stainless steel cauldron, reactor is put into GZX-9030MBE electric heating gas blower.At 50-200 degree Celsius of lower crystallization 0.1-7 days, naturally cool to room temperature, precipitate particle shape crystal.
In the process of synthesis ligand polymer, find that benzoglyoxaline has abundant coordination mode and bridge linking effect to 2-(pyridine-4 base), and 4-(1-propyloic) phenylformic acid improves dimension and the stability of compound by bridging and sequestering action.Construct the ligand polymer with good stability.
Beneficial effect of the present invention: nickel of the present invention, cobalt, or copper coordination polymer obtains under hydrothermal synthesizing condition, preparation method's technique is simple, and good stability, the fault in material be synthesized is few, and degree of crystallinity is high.The polymkeric substance of this mixed ligand has extraordinary potential application prospect in fields such as biological activity, molecular magnet, molecular luminescences.
Accompanying drawing explanation
The ligand polymer C of Fig. 1, mixed ligand of the present invention 22h 19n 3mO 5, with the coordination environment figure of metal center Ni.
The ligand polymer C of Fig. 2, mixed ligand of the present invention 22h 19n 3mO 5, with the one-dimensional chain figure of the coordination of metal center Ni.
The ligand polymer C of Fig. 3, mixed ligand of the present invention 22h 19n 3mO 5, with the two-dimensional layer figure of the coordination of metal center Ni.
The ligand polymer C of Fig. 4, mixed ligand of the present invention 22h 19n 3mO 5, with the accumulation graph of the coordination of metal center Ni.
The infared spectrum of Fig. 5, nickel ligand polymer of the present invention.
The infared spectrum of Fig. 6, cobalt coordination polymer of the present invention.
The infared spectrum of Fig. 7, copper coordination polymer of the present invention.
Embodiment
Below in conjunction with embodiment, the present invention will be described in detail, and embodiment is only the preferred embodiment of the present invention, is not limitation of the invention.
Embodiment 1 (C 22h 19n 3niO 5)
By 4-(1-propyloic) phenylformic acid (0.1mmol) and 2-(pyridine-4 base) benzoglyoxaline (0.1mmol), sodium hydroxide (0.18mmol), and Ni (NO 3) 2 .6H 2o (0.1mmol) is dissolved in 6mL distilled water and puts into tetrafluoroethylene reactor, reactor is put into GZX-9030MBE electric heating gas blower.Set temperature scope is 160 degree, heats 3 days.Be down to room temperature with 5 DEG C/h afterwards and filter the ligand polymer C obtaining described mixed ligand 22h 19n 3niO 5, productive rate is 58.18% (based on Ni).
Embodiment 2 (C 22h 19n 3coO 5)
By 4-(1-propyloic) phenylformic acid (0.1mmol) and 2-(pyridine-4 base) benzoglyoxaline (0.1mmol), sodium hydroxide (0.18mmol) and CoSO 4 .7H 2o (0.1mmol) is dissolved in 6mL distilled water and puts into tetrafluoroethylene reactor, reactor is put into GZX-9030MBE electric heating gas blower.Set temperature scope is 160 degree, heats 3 days.Be down to room temperature with 5 DEG C/h afterwards and filter the ligand polymer C obtaining described mixed ligand 22h 19coO 5, productive rate is 58.14% (based on Co).
Embodiment 3 (C 22h 19n 3cuO 5)
By 4-(1-propyloic) phenylformic acid and 2-(pyridine-4 base) benzoglyoxaline (0.1mmol), sodium hydroxide (0.18mmol), and CuSO 4 .5H 2o (0.1mmol) is dissolved in 6mL distilled water and puts into tetrafluoroethylene reactor, reactor is put into GZX-9030MBE electric heating gas blower.Set temperature scope is 160 degree, heats 3 days.Be down to room temperature with 5 DEG C/h afterwards and filter the ligand polymer C obtaining described mixed ligand 22h 19cuO 5, productive rate is 53.31% (based on Cu).
Then the ligand polymer of above-mentioned mixed ligand is carried out structural characterization
The ligand polymer of this mixed ligand is by single crystal structure diffraction and complete with SHELXTL routine package on PC.The crystallographic parameter of title complex 1 is in table 1.
Fig. 1 obtains C by single crystal diffraction method 22h 19n 3niO 5structure.As we can see from the figure, containing Ni (II) ion in its asymmetric cell, a 4PBI, a L negatively charged ion and a coordinated water molecule.Ni (II) ion is the octahedral configuration of inclination a little of hexa-coordinate and an atom N and five O Atomic coordinates.This atom N comes from the nitrogen-atoms of the pyridine group of 4PBI, and bond distance's distance of Ni-N is 2.0580 (2).Five O atoms come from four Sauerstoffatoms of two L negatively charged ion and the Sauerstoffatom of a coordinated water molecule, and the scope of bond distance's distance of Ni-O is 2.0330 (2) – 2.1540 (2).
With the one-dimensional chain figure of the coordination of metal center Ni shown in Fig. 2.As shown in the figure, each adjacent Ni (II) passes through L 2-the hand tail of part is connected to form along the outward extending one-dimensional catenary structure of b axle.
Fig. 3 is with the two-dimensional layer figure of the coordination of metal center Ni.As shown in the figure, form intramolecular hydrogen bond (O – HO) between the Sauerstoffatom of the Sauerstoffatom in coordinated water and L negatively charged ion, its bond distance and bond angle are 1.92 (3) and 168 (3) ° respectively.The supramolecular structure extending to two-dimensional surface from one-dimensional chain is made by this hydrogen bond.
Fig. 4 is with the accumulation graph of the coordination of metal center Ni.As shown in the figure, we can find the O – HN hydrogen bond of two types and the C – HO hydrogen bond of three types.The O – HN hydrogen bond formed by the oxygen of free water and the nitrogen-atoms of 4PBI, its bond distance and bond angle are 1.88 (2) and 170 (4) ° respectively.And the O – HN hydrogen bond formed by the nitrogen-atoms of the carboxylic acid oxygen and 4PBI that come from L part, its bond distance and bond angle are 1.84 (2) and 170 (4) ° respectively.Simultaneously, as can be seen from Figure 4, the C – HO hydrogen bond of the Sauerstoffatom of L and the carbon atom formation of 4PBI is come from.Its bond distance and bond angle are respectively 2.35 and 125 °.Come from the Sauerstoffatom of coordinated water and form C – HO hydrogen bond from the carbon atom of 4PBI, its bond distance and bond angle are 2.60 and 156 ° respectively.Form C – HO hydrogen bond by oneself in the Sauerstoffatom of L with from the carbon atom in L, its bond distance and bond angle are 2.58 and 140 ° respectively.Except these hydrogen bonds, between aromatic nucleus, also there is the π pi accumulation of two types.A kind of is occur in the π pi accumulation (3.6010 (17)) that imidazoles and phenyl ring class carry out.Another occurs in the π π (3.6434 (16)) that two phenyl ring carry out.These supermolecular mechanism power make two-dimensional layer extend to three-dimensional supramolecular structure.
Fig. 5 is the infrared spectra of the ligand polymer of cobalt: (KBr, cm -1): 3265 (w), 3067 (w), 2970 (w), 1616 (m), 1597 (m), 1564 (s), 1531 (s), 1447 (s), 1406 (s), 1317 (m), 1282 (m), 1238 (w), 1126 (w), 1061 (w), 1022 (m), 972 (m), 916 (m), 866 (m), 847 (w), 818 (m), 788 (w), 761 (m), 743 (s), 694 (m), 640 (w), 563 (w), 516 (w), 438 (w).Fig. 6 is the infrared spectra of the ligand polymer of cobalt: (KBr, cm -1): 3065 (w), 1614 (m), 1541 (m), 1437 (m), 1400 (s), 1315 (m), 1281 (w), 1227 (w), 1142 (w), 1105 (w), 1063 (w), 1018 (w), 964 (w), 837 (w), 814 (w), 748 (s), 567 (m), 520 (w), 440 (w), 407 (w).Fig. 7 is the infrared spectra of the ligand polymer of copper: IR (KBr, cm -1): 3063 (w), 2972 (w), 2758 (w), 1620 (s), 1593 (m), 1528 (s), 1452 (s), 1435 (m), 1406 (s), 1319 (m), 1288 (m), 1240 (w), 1128 (w), 1076 (w), 1060 (w), 1028 (w), 970 (m), 914 (w), 885 (w), 841 (w), 814 (m), 785 (w), 764 (m), 748 (s), 642 (w), 565 (w), 525 (w), 444 (w).
The above embodiment only have expressed embodiments of the present invention; it describes comparatively concrete and detailed; but therefore can not be interpreted as the restriction to the scope of the claims of the present invention; in every case the technical scheme adopting the form of equivalent replacement or equivalent transformation to obtain, all should drop within protection scope of the present invention.

Claims (8)

1. a transition-metal coordination polymkeric substance, its structural formula is:
In formula: M is the transition metal ion of periodic table of elements period 4.
2. the transition-metal coordination polymkeric substance according to claims 1, is characterized in that, described transition metal ion: Mn, Fe, Zn, Ni, Co or Cu.
3. the preparation method of the transition-metal coordination polymkeric substance according to claims 2, is characterized in that used organic ligand 4-(1-propyloic) phenylformic acid and 2-(pyridine-4 base) mol ratio of benzoglyoxaline is 1-5.
4. the preparation method of the transition-metal coordination polymkeric substance according to claims 2, is characterized in that the molar weight of used transition metal ion is for 0.05-1.0mmoL.
5. the preparation method of the transition-metal coordination polymkeric substance according to claims 2, is characterized in that the molar weight of used sodium hydroxide is for 0.05-0.5mmoL.
6. the preparation method of the transition-metal coordination polymkeric substance according to claims 2, it is characterized in that used water, methyl alcohol, ethanol, dimethyl formamide, methyl-sulphoxide, ethylene glycol, glycol dimethyl ether, second two monomethyl ether are as a kind of or mixed solvent, it uses volume to be 0.5-10ml.
7. the preparation method of the transition-metal coordination polymkeric substance according to claims 2, is characterized in that selected temperature range is from 50 to 200 degrees Celsius.
8. the preparation method of the transition-metal coordination polymkeric substance according to claims 2, is characterized in that reacted time range is 0.1 to 7 days.
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105820047A (en) * 2016-03-21 2016-08-03 齐鲁工业大学 Three isomorphic complexes based on aromatic dicarboxylic acid ligand and synthesis method thereof
CN105820346A (en) * 2016-04-27 2016-08-03 齐鲁工业大学 Synthetic method of cadmium coordination polymer containing pyridyl benzimidazole and isophthalic acid
CN105884804A (en) * 2016-04-27 2016-08-24 齐鲁工业大学 Synthesis method of terephthalic acid containing cadmium coordination polymer
CN108395539A (en) * 2018-02-12 2018-08-14 汕头大学 A kind of MOF materials of 3D-DNA network topology structures and its synthesis and application
CN111234243A (en) * 2019-12-31 2020-06-05 郑州轻工业大学 Metal organic framework material, preparation method thereof and immunosensor

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CN102973572A (en) * 2012-11-28 2013-03-20 玉林师范学院 Cervical cancer cell inhibitor and preparation method thereof
CN104230968A (en) * 2014-09-09 2014-12-24 段晶晶 Cadmium-containing dual-core polymer with mixed-ligand and preparation method of cadmium-containing dual-core polymer
CN104292247A (en) * 2014-09-09 2015-01-21 段晶晶 Cadmium-containing two dimensional polymer having mixed ligand, and its preparation method
CN104557992A (en) * 2015-02-26 2015-04-29 天津师范大学 Naphthalene bistriazole trimesinic acid cadmium complex with potential fluorescent material and preparation method thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102973572A (en) * 2012-11-28 2013-03-20 玉林师范学院 Cervical cancer cell inhibitor and preparation method thereof
CN104230968A (en) * 2014-09-09 2014-12-24 段晶晶 Cadmium-containing dual-core polymer with mixed-ligand and preparation method of cadmium-containing dual-core polymer
CN104292247A (en) * 2014-09-09 2015-01-21 段晶晶 Cadmium-containing two dimensional polymer having mixed ligand, and its preparation method
CN104557992A (en) * 2015-02-26 2015-04-29 天津师范大学 Naphthalene bistriazole trimesinic acid cadmium complex with potential fluorescent material and preparation method thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105820047A (en) * 2016-03-21 2016-08-03 齐鲁工业大学 Three isomorphic complexes based on aromatic dicarboxylic acid ligand and synthesis method thereof
CN105820346A (en) * 2016-04-27 2016-08-03 齐鲁工业大学 Synthetic method of cadmium coordination polymer containing pyridyl benzimidazole and isophthalic acid
CN105884804A (en) * 2016-04-27 2016-08-24 齐鲁工业大学 Synthesis method of terephthalic acid containing cadmium coordination polymer
CN108395539A (en) * 2018-02-12 2018-08-14 汕头大学 A kind of MOF materials of 3D-DNA network topology structures and its synthesis and application
CN111234243A (en) * 2019-12-31 2020-06-05 郑州轻工业大学 Metal organic framework material, preparation method thereof and immunosensor
CN111234243B (en) * 2019-12-31 2021-10-01 郑州轻工业大学 Metal organic framework material, preparation method thereof and immunosensor

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