CN111732614A - Synthetic method of novel eutectic cobalt complex - Google Patents

Synthetic method of novel eutectic cobalt complex Download PDF

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CN111732614A
CN111732614A CN202010648610.8A CN202010648610A CN111732614A CN 111732614 A CN111732614 A CN 111732614A CN 202010648610 A CN202010648610 A CN 202010648610A CN 111732614 A CN111732614 A CN 111732614A
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phenanthroline
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黄秋萍
韦友欢
曾振芳
黄秋婵
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Guangxi Normal University for Nationalities
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Abstract

A novel eutectic cobalt complex belongs to the triclinic system, P ī space group, and has a chemical formula of [ Co (1,10-phen)2(AcO)]·H2SDA·11H2And O. Putting 1,10-phenanthroline, 4' -diphenylethylene dicarboxylic acid and sodium hydroxide solid into a polytetrafluoroethylene substrate hydrothermal reaction kettle with the volume of 30mL, adding dimethylformamide and water, stirring, adding cobalt acetate, adjusting the pH value, and then putting into the reaction kettle for constant-temperature reaction. And taking out the reaction kettle after the reaction is finished, naturally cooling the reaction kettle at room temperature, filtering the reaction kettle, and standing the filtrate. Naturally volatilizing and crystallizing for three days at room temperature. The research result of the fluorescence property shows that the eutectic cobalt complex has certain fluorescence at low concentrationThe fluorescent material has good photoluminescence performance, the fluorescence intensity is gradually reduced or even quenched along with the increase of the concentration of the solution, and the fluorescent concentration self-quenching effect exists.

Description

Synthetic method of novel eutectic cobalt complex
Technical Field
The invention relates to a complex and a synthetic method thereof, in particular to a complexIs a novel eutectic cobalt complex [ Co (1,10-phen)2(AcO)]·H2SDA·11H2And (3) a synthetic method of O.
Background
In recent years, the design and synthesis of functional complexes have been extensively studied and focused by people due to their unique frameworks and topological structures and their potential applications in the fields of catalysis, magnetism, luminescence, and gas absorption. In the synthesis of functional complexes, many factors such as the structural characteristics of organic ligands, the coordination environment of metal ions, counter anions, solvent systems, reaction temperature and the pH value of the system influence the final structure of the complexes. Therefore, even after many years of research, the structure of functional complexes is difficult to predict accurately. Among them, the choice of metal ions and the structure of organic ligands are particularly important, and the structure and properties of the complex can be directly influenced. Compared with other ligands, the aromatic carboxylic acid ligand not only has the characteristic of diversified coordination modes of the carboxylic acid ligand, the special framework aromatic ring structure of the aromatic carboxylic acid ligand is easy to generate pi-pi stacking, and the oxygen atom in the carboxylic acid is also easy to form hydrogen bond by hydrogen ions in the structure, so that the structure and the performance of the synthesized metal-aromatic carboxyl complex have certain influence. The stilbene dicarboxylic acid derivative is used as an organic ligand, still has hydrogen bonding capability as a proton acceptor after the carboxyl group of the stilbene dicarboxylic acid derivative is coordinated, a benzene ring is a potential pi-pi action site, and the interaction information is stored in the generated complex structure and is possible to play a guiding role in the formation of a stacking structure. Besides aromatic carboxylic acid, the skeleton structure of the common rigid ligand is fixed, the common rigid ligand is not easy to deform during coordination, the structure is easy to control, and the common rigid ligand is widely applied to synthesis of functional complexes by researchers.
Disclosure of Invention
Aiming at the defects of the prior art, the invention adopts a solvothermal method, takes 4, 4' -diphenylethylene dicarboxylic acid and 1,10-phenanthroline as ligands, and constructs a novel eutectic cobalt complex [ Co (1,10-phen)2(AcO)]·H2SDA·11H2O, 1,10-phen ═ 1,10-phenanthroline, H 24, 4' -Diphenylenedicarboxylic acid (SDA)Acid, and the crystal structure and the fluorescence property of the acid are researched.
In order to achieve the purpose, the invention adopts the following technical scheme:
a novel eutectic cobalt complex of the formula [ Co (1,10-phen)2(AcO)]·H2SDA·11H2O, wherein 1,10-phen ═ 1,10-phenanthroline, H 24, 4' -diphenylethylene dicarboxylic acid, wherein the crystallographic parameters of the novel eutectic cobalt complex are shown in table 1, the partial bond length and the bond angle of the novel eutectic cobalt complex are shown in table 2, and the bond length and the bond angle of the hydrogen bond of the novel eutectic cobalt complex are shown in table 3.
Compared with the prior art, the invention has the following beneficial effects:
by adopting a solvothermal method, 4' -diphenylethylene dicarboxylic acid and 1,10-phenanthroline are used as directional ligands, and the conditions of raw material molar ratio, reaction solvent, pH value, reaction time, reaction temperature and the like of the reaction are adjusted, a novel eutectic cobalt complex [ Co (1,10-phen) is successfully constructed2(AcO)]·H2SDA·11H2And O. And the structure of the complex is characterized by methods such as IR (infrared radiation) and elemental analysis, and the single crystal structure is obtained by X-ray single crystal diffraction measurement. The single crystal structure of the eutectic cobalt complex comprises an independent mononuclear cobalt complex formed by coordination of 1,10-phenanthroline and cobalt acetate, an independent 4, 4' -diphenylethylene dicarboxylic acid and 11 free water molecules. The research result of the fluorescence property of the cobalt eutectic complex shows that the eutectic cobalt complex has certain fluorescence intensity at low concentration and good photoluminescence performance, the fluorescence intensity is gradually reduced or even quenched along with the increase of the concentration of the solution, and the self-quenching effect of the fluorescence concentration exists.
Drawings
FIG. 1 is the crystal structure of the complex.
FIG. 2 is a three-dimensional stacking diagram of the complex.
FIG. 3 is an infrared absorption spectrum of the complex and the ligand.
FIG. 4 is a thermogravimetric plot of the complex.
FIG. 5 is a fluorescence spectrum of the complex.
Detailed Description
The technical solution of the present invention is further illustrated by the following examples.
Example 1
1 experimental part
1.1 instruments and reagents
Agilent G8910ACCD single crystal diffractometer; Perkin-Elmer 240Q elemental analyzer; bruker Vector22FT-IR type infrared spectrometer; RF-5301 PC-type fluorescence spectrometer. All reagents were analytically pure and purchased from Shingan chemical Co. The safe temperature of the polytetrafluoroethylene substrate hydrothermal reaction kettle is 220 ℃, the highest pressure is 3Mpa, the polytetrafluoroethylene substrate hydrothermal reaction kettle is formed by fine processing of high-quality nonmagnetic 0Cr18Ni9Ti stainless steel, a polytetrafluoroethylene lining is arranged in the polytetrafluoroethylene substrate hydrothermal reaction kettle, and the polytetrafluoroethylene substrate hydrothermal reaction kettle is double-layer nursing and acid and alkali resistant. The 1,10-phenanthroline is called as 1,10-phenanthroline with the british name, and is called as phenanthroline, phenanthroline and phenanthroline for short, and is called as 1,10-phenanthroline and 1,10-phenanthroline, etc.
1.2 Synthesis of Co-crystal complexes
1,10-phenanthroline (0.0991g, 0.5mmol), 4' -diphenylethylene dicarboxylic acid (0.0671g, 0.25mmol) and sodium hydroxide solid (0.2000g, 0.5mmol) are placed in a polytetrafluoroethylene substrate hydrothermal reaction kettle with the volume of 30mL, 7mL of Dimethylformamide (DMF) and 8mL of water are added, a magnetic stirrer is used for stirring for 1 hour, then cobalt acetate (0.0443g, 0.25mmol) is added, the mixture is stirred for half an hour, the pH value is adjusted to be about 10, the mixture is continuously stirred for 30 minutes and then placed in the reaction kettle, and an electrothermal blowing dry box with the temperature of 160 ℃ is placed for constant temperature reaction for 3 days. And taking out the reaction kettle after the reaction is finished, naturally cooling the reaction kettle for 12 hours at room temperature, filtering the reaction kettle, and keeping the filtrate standing. Naturally volatilizing for three days at room temperature to crystallize, and collecting red crystal [ Co (1,10-phen)2(AcO)]·H2SDA·11H2O。
Yield 37.0mg, yield 78.4% (based on 1, 10-phen).
IRν：3435(O-H),1610(C＝C),1426(C＝C),1367(C-O),1226(C-O),826(C-H),779(C-H),716(C-H),526(Co-O),477(Co-N)cm-1。Anal.calcd for C42H53N4O17Co:C,53.39；H,5.65；N,5.93；found C,50.42；H,5.63；N,5.90。
1.3 Crystal Structure resolution
The test specimen (0.13mm × 0.12.12 mm × 0.10.10 mm) was placed on an Agilent CCD single crystal diffractometer using
Figure BDA0002574075970000033
Radiation of radiation
Figure BDA0002574075970000032
Collecting data in an omega-2 theta scanning mode at room temperature, wherein theta is within a range of 3.78-27.28 degrees (1), performing Lp factor correction and absorption correction by using an SADABS program, determining the position of metal ions by using a Parterson method, calculating hydrogen atom coordinates by using a hydrogenation theory, and finally correcting all structural data by using a least square method. The calculation process is completed by using the programs of SHELXS-97, SHEXL-97 and Olex 2.
2 results and discussion
2.1 description of the Crystal Structure
TABLE 1 Crystal parameters of the complexes
Figure BDA0002574075970000031
Figure BDA0002574075970000041
TABLE 2 partial bond lengths and bond angles of the complexes
Figure BDA0002574075970000042
TABLE 3 bond length and bond angle of hydrogen bonding of the complexes
Figure BDA0002574075970000043
Figure BDA0002574075970000051
The eutectic cobalt complex belongs to a triclinic system, P ī space group, and the crystallographic parameters, partial bond length bond angles and hydrogen bond parameters are shown in tables 1, 2 and 3 respectively. From eutectic cobalt complexes [ Co (1,10-phen)2(AcO)]·H2SDA·11H2O (1,10-phen ═ 1,10-phenanthroline, H2Crystal structure of SDA ═ 4,4 '-diphenylethylene dicarboxylic acid) as can be seen in fig. 1, the structure contains one independent mononuclear cobalt complex and one independent 4, 4' -diphenylethylene dicarboxylic acid and 11 water molecules. This eutectic compound contains 1 mononuclear cobalt complex as well as 1 4, 4' -diphenylethylene dicarboxylic acid and 11 free water molecules. The 11 solvent water molecules free in the structure have no strong bonding effect with the main structure and are in a disordered state, so that wR in the crystal parameters2The value is too large. In an independent mononuclear cobalt complex structure, the valence of cobalt ions can be obtained to be +2 based on the bond length of conventional Co-O and Co-N bonds and the molecular charge neutrality principle. Co (II) is in a hexa-coordinated coordination environment and is respectively linked with four nitrogen atoms from two 1,10-phenanthroline rings
Figure BDA0002574075970000052
Figure BDA0002574075970000053
With one acetic acid having two oxygen atoms
Figure BDA0002574075970000054
Figure BDA0002574075970000055
And (4) carrying out coordination. N (1), N (3), N (4) and O (1) form the equatorial plane of an octahedron, 0.4828x-0.3718y-0.7929 z-6.0645 is the optimal equation of a two-times plane, and four atoms on the equatorial plane averagely deviate
Figure BDA0002574075970000057
O (2) and N (2) are two vertexes of an octahedron, and the distances from the plane to the two vertexes are respectivelyIs that
Figure BDA0002574075970000056
Co (II) is offset from the plane by a distance of
Figure BDA0002574075970000058
CoN to make it form twist4O2Octahedral configuration. In the eutectic structure, O-H.O hydrogen bonding exists between water molecules and between solvent water molecules and oxygen atoms of stilbene dicarboxylic acid ligands, as shown in a structural diagram, and specific hydrogen bonding parameters are shown in Table 3. The three-dimensional stacking diagram is shown in fig. 3, in the complex, the one-dimensional chain of the complex 1 is stacked to form a two-dimensional plane structure through the pi · pi action of the 1,10-phenanthroline ring between molecules, the chains of adjacent layers are parallel, and the two-dimensional structure is further interleaved to form a three-dimensional structure through the pi · pi action of the other 1,10-phenanthroline ring in the structure, as shown in fig. 2.
2.2 Infrared spectroscopic analysis of the Complex
The infrared absorption spectrum of the complex is shown in FIG. 3, 3435cm–1Is the O-H stretching vibration peak of free water molecules, 1610cm–1、1426cm–1Is a characteristic peak of C ═ C stretching vibration, 1367cm–1And 1226cm–1Is C-O stretching vibration peak, 826cm–1Is a deformed vibration peak of a C-H bond of a benzene ring, and is 779cm-1And 716cm–1Is the peak of C-H external bending vibration on the pyridine ring. 526cm–1And 477cm–1The peak is the stretching vibration peak of Co-O, Co-N, which shows that cobalt ion participates in coordination.
2.3 thermal stability
The TGA curve of the thermal analysis of the complex is shown in FIG. 4, and the analysis is carried out under nitrogen gas at a temperature rise rate of 10 ℃/min. Thermogravimetric analysis shows that the weight loss rate of the title complex is 19.8% at 45-220 ℃, and 11 free solvent water molecules in the crystal structure are lost; with the rise of the temperature, the complex continues to lose weight, the weight loss rate is 25% at 225-410 ℃, and the lost is eutectic H2SDA ligand. When the temperature is higher than 410 ℃, the complex framework structureAnd (3) instability and decomposition begin to occur, wherein the weight loss rate is 21% at the temperature of 410-600 ℃, one 1,10-phenanthroline ligand participating in coordination is lost, the weight loss rate is 28% at the temperature of 600-700 ℃, the complex skeleton is continuously decomposed, and the other 1,10-phenanthroline ligand and acetate which are coordinated are lost successively. The final residue may be the metal oxide CoO.
2.4 fluorescence Properties
Under the irradiation of a 365nm ultraviolet lamp, a certain concentration of complex DMF solution (1 × 10-5mol/L) emits certain fluorescence, and shows that the target complex has certain luminescence performance, and the fluorescence intensity of the target complex is stronger than that of the ligand 1,10-phenanthroline and 4, 4' -diphenylethylene dicarboxylic acid, the luminescence mode of the ligand and the complex belongs to pi → pi electron transition in the ligand, and the stronger luminescence intensity of the complex is because the rigidity of the structure is enhanced after the ligand is coordinated, the energy proportion consumed by vibration relaxation after excitation is reduced, and meanwhile, the concentration of the complex is respectively measured to be 5 × 10-5mol/L、1×10-5mol/L、5×10-6mol/L、1×10-6mol/L、5×10-7The influence of the concentration on the fluorescence intensity of the eutectic complex DMF solution in mol/L is researched by the fluorescence spectrum of the eutectic complex DMF solution in mol/L. As shown in fig. 5, the fluorescence intensity of the co-crystal compound decreased significantly with increasing solution concentration, indicating that it had a fluorescence self-quenching effect.

Claims (5)

1. A novel eutectic cobalt complex, characterized in that the novel eutectic cobalt complex has the chemical formula [ Co (1,10-phen)2(AcO)]·H2SDA·11H2O, wherein 1,10-phen ═ 1,10-phenanthroline, H24, 4' -diphenylethylene dicarboxylic acid (SDA), belonging to the triclinic system, P ī space group, wherein the crystallographic parameters of the novel eutectic cobalt complex are shown in Table 1, the partial bond length and the bond angle of the novel eutectic cobalt complex are shown in Table 2, and the bond length and the bond angle of the hydrogen bond of the novel eutectic cobalt complex are shown in Table 3.
Table 1 list of crystallographic parameters of the novel eutectic cobalt complexes
Figure FDA0002574075960000011
Figure FDA0002574075960000021
Part of the bond length and bond angle of the novel eutectic cobalt complexes described in Table 2
Figure FDA0002574075960000022
Bond length and bond angle of hydrogen bonds of the novel eutectic cobalt complexes described in Table 3
Figure FDA0002574075960000023
Figure FDA0002574075960000031
2. Novel eutectic cobalt complex [ Co (1,10-phen)2(AcO)]·H2SDA·11H2A process for synthesizing O, which comprises reacting a compound of formula (I),
reagent and its usage
1,10-phenanthroline, 4' -diphenylethylene dicarboxylic acid, sodium hydroxide and cobalt acetate are used as reactants,
the mass ratio of the 1,10-phenanthroline to the 4, 4' -diphenylethylene dicarboxylic acid to the sodium hydroxide to the cobalt acetate is 1.8-2.2: 0.8-1.2: 1.8-2.2: 0.8-1.2;
DMF and water are taken as solvents to prepare the intermediate,
the dosage of the DMF is calculated by adding 6.5-7.5 mL of DMF into every 0.5mmol of 1,10-phenanthroline,
the dosage of the water is calculated by adding 7.5-8.5 mL of water into every 0.5mmol of 1, 10-phenanthroline;
(II) operation step of synthetic reaction
(1) Weighing each reactant according to the proportion in the step (A) for later use, and weighing a solvent according to the proportion in the step (A) for later use;
(2) putting the 1,10-phenanthroline, 4' -diphenylethylene dicarboxylic acid and sodium hydroxide in the step (1) into a reaction kettle;
(3) adding the DMF and the water in the step (1) into a reaction kettle, and uniformly stirring;
(4) adding the cobalt acetate obtained in the step (1) into a reaction kettle, and uniformly stirring;
(5) adjusting the pH value of the reaction system to 9.5-10.5, and uniformly stirring;
(6) placing the reaction kettle in a drying oven at 150-170 ℃ for constant-temperature reaction until the reaction is finished;
(7) taking the reaction kettle out of the drying box, placing the reaction kettle at room temperature for natural cooling, and filtering to obtain filtrate;
(8) at room temperature, naturally volatilizing the filtrate to crystallize to obtain a crystal, namely [ Co (1,10-phen)2(AcO)]·H2SDA·11H2O。
3. The novel eutectic cobalt complex [ Co (1,10-phen) according to claim 22(AcO)]·H2SDA·11H2The synthesis method of O is characterized in that the reaction kettle is a polytetrafluoroethylene substrate hydrothermal reaction kettle.
4. The novel eutectic cobalt complex [ Co (1,10-phen) according to claim 22(AcO)]·H2SDA·11H2The synthesis method of O is characterized in that in the step (4), the pH value is adjusted by using a sodium hydroxide solution.
5. The novel eutectic cobalt complex [ Co (1,10-phen) according to claim 22(AcO)]·H2SDA·11H2The synthesis method of O is characterized in that the mass ratio of the 1,10-phenanthroline to the 4, 4' -diphenylethylene dicarboxylic acid to the sodium hydroxide to the cobalt acetate is 2:1:2: 1.
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CN112321650A (en) * 2020-11-25 2021-02-05 广西民族师范学院 Preparation method and application of novel cobalt complex with two-dimensional structure

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