CN114920946B - Dicarboxylic acid Ni (II) water-based electrochromic coordination polymer with 2D-3D poly-locking structure and preparation method thereof - Google Patents
Dicarboxylic acid Ni (II) water-based electrochromic coordination polymer with 2D-3D poly-locking structure and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a water-based electrochromic coordination polymer with a 2D-3D poly-locking structure and a preparation method thereof, wherein the coordination polymer has the following chemical formula: [ Ni (L1) (L2) (H) 2 O)(DMF)]∙ DMF. A certain amount of Ni (NO 3 ) 2 ·6H 2 O, N N '-bis (4-pyridyl) -1,4,5, 8-naphthalenediimide (L1), 4' -stilbenedicarboxylic acid (H) 2 L2) and a certain amount of deionized water and N, N' -Dimethylformamide (DMF) are sealed and heated for a period of time at a certain temperature in a reaction kettle with a polytetrafluoroethylene lining, and after the reaction is finished, the mixture is naturally cooled to room temperature, so that yellow crystals are obtained, namely the electrochromic complex with a 2D-3D poly-lock structure. The synthesis method of the invention has simple operation, good repeatability and high product yield; water and a small amount of DMF are taken as solvents, so that the method is environment-friendly; the temperature range required by the color change of the coordination polymer is wider (150-267 ℃), the coordination polymer can change the color in various ways, and the color change is sensitive; the coordination polymer has good stability and can be repeatedly used.
Description
Technical Field
The invention belongs to the technical field of chemistry, and relates to a coordination polymer, in particular to a dicarboxylic acid Ni (II) water-based electrochromic coordination polymer with a 2D-3D poly-lock structure and a preparation method thereof.
Background
In recent years, a visual color-changing material capable of changing a color visible to the naked eye under the stimulation of an external signal has been attracting attention due to its application in various fields such as sensing, inkless-erasable printing, and forgery prevention. The color change phenomenon can be classified into photochromism, electrochromic, thermochromic, solvent-induced color change, mechanochromism, etc., according to the kind of external signal. However, most photochromic, electrochromic, thermochromic and mechanochromatic processes require intense external signal stimuli, such as varying light intensities, high voltages, high temperatures and specific mechanical thresholds. These limit their wide and convenient application in daily production and life. By a water-based electrochromic material is meant a material that is capable of undergoing a change in light absorption or emission properties when stimulated by water. The water-based electrochromic process is one of the solvent-based electrochromic processes, and is relatively mild in comparison with the external stimulus required. The color change of the dehydration process can generally be achieved by heating, contact with a desiccant or vacuum drying. The water absorption color change process can only be realized by contacting the surface of the material with liquid water or water vapor. Based on this feature, the water-based electrochromic materials can be used in the visual monitoring, carbon paper, humidity sensor, human sweat pore mapping, and paint and coating industries.
Coordination polymers are a relatively bulky class of hybrid materials. Because there are an infinite number of combinations of metal ions and organic ligands that make up the coordination polymer, the coordination polymer also has an infinite variety of structures and properties, making it suitable for building color-changing materials. Among various organic ligands, pi electron-deficient naphthalimide derivatives can respond well to external light, electricity, heat and other stimuli, generate naphthalimide free radicals through an electron reduction process, and generate color change. The polycarboxylic acid ligand is an electron-rich substance and can be used as an electron donor when the color-changing material is constructed. Thus, a combination of a naphthalimide derivative and a polycarboxylic acid ligand can be used to construct a water-borne color-changing coordination polymer.
On the other hand, in recent years, coordination polymers having an entangled structure have been receiving particular attention in their attractive topology and wide application in many fields such as adsorption, molecular recognition, and sensing. Various entanglement structures such as polythreading, coalescence, polyrotaxane and polylock have been reported to date. In these systems, coordination polymers having a polymodal structure have high flexibility and stability, and when dehydration or water absorption occurs, the crystal lattice can be compressed or expanded while maintaining the stability of the framework, shortening or extending the distance between the electron donor and the electron acceptor, thereby controlling the transfer of electrons and the generation or quenching of free radicals. Coordination polymers having a polymodal structure are therefore suitable for use as a water-borne electrochromic material.
Current research on the electrochromic materials is mainly focused on organic materials. Compared with the organic water-based color change material, the water-based color change coordination polymer can combine the thermal stability and high strength of inorganic compounds and can synergistically generate some new excellent performances while keeping the advantage of easy modification and processing of organic compounds. Therefore, the research of the water-based electrochromic coordination polymer is one of the current research hotspots.
Disclosure of Invention
The purpose of the invention is that: the dicarboxylic acid Ni (II) water-based electrochromic coordination polymer with the 2D-3D poly-locking structure and the preparation method thereof are provided, the synthesis method is simple to operate, the product yield is high, the environment is protected, the complex is discolored in a plurality of modes, the discoloration is sensitive, the temperature range required by the discoloration is wider, the stability is good, and the complex can be repeatedly utilized.
The technical scheme of the invention is as follows: the dicarboxylic acid Ni (II) water-based electrochromic coordination polymer with a 2D-3D poly-lock structure has the following chemical formula: [ Ni (L1) (L2) (H) 2 O)(DMF)]∙ DMF; its crystal belongs to orthorhombic system and its space group isPnmaThe unit cell parameters area = 14.8652(6) Å，b = 25.7884(12) Å，c = 10.9334(5) Å，α = 90°，β = 90°，γ = 90°，V = 4193.3(3) Å 3 。
Wherein, the dicarboxylic acid Ni (II) water-based electrochromic coordination polymer with a 2D-3D poly-locking structure comprises the following steps: mixing a certain amount of reaction raw materials with a certain amount of solvent, sealing and reacting for a period of time in a reaction kettle with a polytetrafluoroethylene lining at a certain temperature, naturally cooling to room temperature after the reaction is finished, filtering, washing and drying to obtain yellow crystals, namely the dicarboxylic acid Ni (II) water-based electrochromic coordination polymer with a 2D-3D poly-locking structure.
Wherein the reaction raw materials are metal salts and ligands; the metal salt is Ni (NO) 3 ) 2 ·6H 2 O, ligand L1, H 2 L2; the solvent is de-removedA mixture of ionized water and DMF.
Wherein, L1 is N, N' -di (4-pyridyl) -1,4,5, 8-naphthalimide, H 2 L2 is 4,4 '-stilbenedicarboxylic acid and DMF is N, N' -dimethylformamide.
Wherein, the specific reaction conditions are as follows: the mass volume ratio of the reaction raw materials to the solvent is 127 mg:10 mL; metal salts, ligands L1, H in the reaction raw materials 2 The mass ratio of L2 is 58:42:27; the volume ratio of deionized water to DMF in the solvent was 19:1, a step of; the reaction temperature is 90 ℃; the reaction time was 70 hours.
The invention has the advantages that: 1. the preparation method is simple to operate, good in repeatability, high in product yield, environment-friendly and environment-friendly, and water and a small amount of DMF are taken as solvents. 2. The temperature range required by the color change of the complex is wider (150-267 ℃), the complex can change the color in various ways, and the color change is sensitive. 3. The complex has good stability and can be repeatedly utilized.
Drawings
FIG. 1 is a diagram of the coordination environment of Ni (II) ions in a complex;
FIG. 2 is a diagram showing the structure of a 2D layer formed by Ni (II) and L1 ligands in a complex and a simplified topology;
FIG. 3 is an interlocking structural diagram of two-dimensional layers arranged in two different directions in a complex;
FIG. 4 is a 2D to 3D lock topology diagram of the complex;
FIG. 5 is a water-borne photo of the complex;
FIG. 6 is an electron paramagnetic vibration spectrum of the complex at room temperature and 150 ℃.
FIG. 7 is a UV-vis absorption spectrum of the complex before and after water loss.
Detailed Description
The following is a further explanation of the technical solution of the present invention with reference to the drawings and examples, and the conditions used in this example are the optimal solution obtained after a number of parallel experiments, under which the crystal most suitable for the test is obtained. The crystals cannot be obtained or are unsuitable for testing by changing the reactant ratio, temperature or time.
Examples: ni (NO) of 0.058 g 3 ) 2 ·6H 2 O, L1 of 0.042 g, H of 0.027 g 2 The mixture of L2, 9.5 mL deionized water and 0.5 mL DMF is sealed and reacted for 70 hours at 90 ℃ in a reaction kettle with polytetrafluoroethylene lining of 20 mL, and after the reaction is finished, the mixture is naturally cooled to room temperature, and yellow crystals are obtained after filtration, washing and drying, namely the dicarboxylic acid Ni (II) water-based electrochromic coordination polymer with a 2D-3D poly-lock structure, and the yield is 47%.
The main infrared absorption peaks of the obtained coordination polymer are as follows: 3407 (m), 3069 (w), 2935 (m), 1935 (w), 1725(s), 1675(s), 1600(s), 1585(s), 1554(s), 1500 (m), 1450(s), 1388(s), 1340(s), 1249(s), 1193 (m), 1146 (m), 1122 (m), 1094 (m), 1063 (w), 1015 (w), 984 (w), 868 (w), 840 (m), 793(s), 757 (m), 710 (m), 690 (w), 634(s).
The coordination polymer obtained above is characterized as follows:
(1) Crystal structure determination: the diffraction data were collected on a Bruker SMART APEX II diffractometer using Mo K α Radiation @λ= 0.71073 a), temperature 173K; correction using a technical scan; the crystal structure is solved by a direct method through a SHELXS-2013 program, and the SHELEXL-2013 program is used for finishing by a full matrix least square method; the temperature factor of the non-hydrogen atom is corrected by anisotropy; detailed crystallographic data are presented in table 1; representative bond lengths and bond angles are shown in table 2; the hydrogen bonding data are shown in Table 3. The crystal structure of the complex is shown in FIGS. 1-4.
The crystal of the obtained complex belongs to an orthorhombic system, and the space group isPnmaThe unit cell parameters area = 14.8652(6) Å，b = 25.7884(12) Å，c = 10.9334(5) Å，α = 90°，β = 90°，γ = 90°，V = 4193.3(3) Å 3 . The asymmetric units of the complex comprise half Ni (II) ions, half L1 anions, half L2 anions, half coordinated water molecules, half coordinated DMF molecules and half lattice DMF molecules. The Ni (II) ion is in a hexacoordinated octahedral coordination configuration with two nitrogen atoms from two different L1 ligands and two different L2 anions, oneFour oxygen atoms of one molecule of water and one molecule of DMF coordinate (see fig. 1). The equatorial position of the octahedron is occupied by two oxygen atoms and two nitrogen atoms (O3, O3 #1 N1 and N1 #1 ) While the vertex position is occupied by two oxygen atoms (O5 and O6). Each L1 ligand coordinates to two Ni (II) ions forming a stair-type chain. L2 further connects the chains in a stair-like shape into a layered structure (see fig. 2). One DMF molecule and one water molecule are coordinated with Ni (II) ions as terminal ligands, and the structure and the dimension of the framework are not affected. From a topological perspective, each Ni (II) can be considered a 4-linked node, and the L1 ligand and L2 anion can be considered a linker. Thus, the two-dimensional layer can be reduced to a Schl ä fli symbol (4 4 ∙6 2 ) Sql-topology network of (see fig. 2). The most interesting structural feature of the complex is that the two-dimensional layers are arranged along two different directions, and each two-dimensional layer is interlocked with innumerable other two-dimensional layers from different directions through Hopf connection (see figure 3) to form a 2D-3D poly-lock frame (see figure 4). In addition, an intramolecular hydrogen bond interaction exists between O5 on the water molecule and O4 of the L2 anion, so that the stability of the complex structure is improved.
(2) Study of the Water-based color-changing Properties: the complex obtained above was heated at 150℃and a color change from yellow to green was observed within 5 minutes. If a sample of the complex is placed in a desiccator containing concentrated sulfuric acid as a desiccating agent, it may also change from yellow to green after a few hours. After the complex turned green was stopped from heating or taken out of the dryer, a change in color from green to yellow was observed after 2 minutes of contact with air (see fig. 5). If the green sample is directly contacted with liquid water, the sample immediately changes from green to yellow. The reversible water-induced color change process of the complex can be repeated for a plurality of times. The complex is very stable and the frame does not collapse before heating to 267 ℃. The color-changing temperature range is wider, and the complex can change from yellow to green by heating in the temperature range of 150-267 ℃. The water-based color change mechanism is that after the complex is heated or dried by concentrated sulfuric acid, coordinated water molecules are lost, and the crystal lattice of the complex is compressed, thereby shortening electron donorThe distance between (electron rich L2 anion) and electron acceptor (electron deficient L1 ligand) is electron transferred, generating naphthalimide radicals, which change the sample from yellow to green. After the green sample contacts with air, water molecules in the absorbed air are coordinated, or the green sample contacts with liquid water and is directly coordinated with the liquid water molecules, so that lattice expansion occurs, the distance between an electron donor and an electron acceptor is restored to the original length, electron transfer is blocked, quenching of free radicals occurs, and the sample is changed from green to yellow. The complex has 2D-3D poly-lock framework, so that the complex has high flexibility and stability. The framework structure can be kept from collapsing during lattice compression and expansion. This mechanism can be demonstrated by electron paramagnetic vibration spectroscopy and UV-vis spectroscopy. Electron paramagnetic vibration spectrum of the complex at 150 DEG CgA free radical signal peak appears at = 2.0038, whereas the complex at room temperature does not (see fig. 6). On the UV-vis spectrum, the complex before water loss has only a very weak absorption peak at 725 and nm, while the absorption peak intensity of the complex after water loss by heating at 725 and nm is greatly increased, so that free radical generation can be proved.
Symmetric code: #1 x, -y + 3/2, z。
Claims (2)
1. a dicarboxylic acid Ni (II) water-based electrochromic coordination polymer with a 2D-3D poly-locking structure is characterized in that the coordination polymer has the chemical formula: [ Ni (L1) (L2) (H2O) (DMF) ] ∙ DMF; the crystal belongs to an orthorhombic system, the space group is Pnma, the unit cell parameters are a= 14.8652 (6) a, b= 25.7884 (12) a, c= 10.9334 (5) a, α=90°, β=90°, γ=90°, v= 4193.3 (3) a 3; wherein: ligand L1 is N, N '-bis (4-pyridyl) -1,4,5, 8-naphthalimide and ligand H2L2 is 4,4' -stilbenedicarboxylic acid.
2. The method for preparing the dicarboxylic acid Ni (II) water-based electrochromic coordination polymer with a 2D-3D poly-lock structure according to claim 1, wherein the preparation method of the coordination polymer is characterized by comprising the following steps: mixing a certain amount of reaction raw materials with a certain amount of solvent, sealing and reacting for a period of time in a reaction kettle with a polytetrafluoroethylene lining at a certain temperature, naturally cooling to room temperature after the reaction is finished, filtering, washing and drying to obtain yellow crystals, namely the dicarboxylic acid Ni (II) water-based electrochromic coordination polymer with a 2D-3D poly-locking structure; the reaction raw materials are metal salt and ligand; the metal salt is Ni (NO 3) 2.6H2O; the solvent is a mixture of deionized water and DMF; the mass volume ratio of the reaction raw materials to the solvent is 127 mg:10 mL; the mass ratio of the metal salt to the ligand L1 to the ligand H2L2 in the reaction raw materials is 58:42:27; the volume ratio of deionized water to DMF in the solvent was 19:1, a step of; the reaction temperature is 90 ℃; the reaction time was 70 hours.
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| JP2011256122A (en) * | 2010-06-07 | 2011-12-22 | Japan Science & Technology Agency | Guest-responsive light emitting material |
| CN105439118A (en) * | 2014-09-28 | 2016-03-30 | 中国科学院大连化学物理研究所 | Method for preparation of bamboo-shaped carbon nanotube by ultrasonic atomization |
| CN109942833A (en) * | 2019-04-25 | 2019-06-28 | 陕西科技大学 | A kind of three-dimensional porous metal zinc coordination polymer and its preparation method and application |
| CN112552523A (en) * | 2020-12-08 | 2021-03-26 | 广西民族师范学院 | [Ni(iptp)2(SDA)2(H2O)2]n and synthetic method |
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