CN112940271B - Phenyl diimide based zinc coordination polymer and preparation method and application thereof - Google Patents
Phenyl diimide based zinc coordination polymer and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to synthesis of an organic-inorganic hybrid color-changing material, in particular to a phenyldiimide-based zinc coordination polymer and a preparation method and application thereof; the chemical formula is [ Zn (4-PMPMPMMD) (BTC)]nxDMF, 4-PMPMPMD ofN,NBis (4-pyridylmethyl) -phenyldiimide, BTC is a carboxylic acid unionized trimesic acid, DMF isN,N-dimethylformamide; the invention provides a photochromic material with ultrafast photo-reversible and super-fatigue resistance of a phenyldiimide-based zinc coordination polymer, which is prepared by taking phenyldiimide with excellent electron deficiency as an electron acceptor and hybridizing the phenyldiimide with an oxygen-containing carboxylic acid electron donor through the coordination of metal zinc.
Description
Technical Field
The invention relates to synthesis of an organic-inorganic hybrid color-changing material, in particular to a phenyldiimide-based zinc coordination polymer and a preparation method and application thereof.
Background
The Electron Transfer (ET) type inorganic-organic hybrid photochromic material shows important practical or potential application value in the fields of sensing, protection, display, switching and the like due to flexible and various compositions and structures and good visual detectability photochromic behavior. The performance indexes of the inorganic-organic hybrid photochromic material are mainly reflected in three aspects: (1) the photoresponse rate and color contrast during color change; (2) reversibility during fading; (3) fatigue resistance during discoloration-fading cycle. Currently, by effectively modulating the electron accepting ability of an acceptor, the electron donating ability of a donor and the matching degree between the two, the self-assembly of an electron donor unit and an acceptor unit is carried out through a specific mode (coordination and/or electrostatic interaction), and some important breakthroughs have been made in the aspects of improving the photoresponse rate and the color contrast in the color change process of inorganic-organic hybrid materials. In 2007, the clever group introduces 4, 4' -bipyridine with excellent electron deficiency characteristics into the clodinium chloride-bismuthate system for the first time, and a crystalline viologen-clodinium chloride bismuthate electron donor-acceptor system based on an intermolecular ET photochromic mechanism is obtained. On the basis, a plurality of research groups at home and abroad develop more comprehensive research on 4,4 ' -bipyridyl electron donor-acceptor hybrid color-changing materials, and the electron-deficient receptor 4,4 ' -bipyridyl and derivatives thereof are hybridized with strong electron donor chlorometalate, carboxylate, molecular sieve, phosphate, carboxyl-containing ligand/solvent and the like in a specific mode, so that a large number of hybrid crystalline state color-changing materials with good photoresponse rate and obvious color difference are constructed, and the matching rules of the electron-deficient receptor of the 4,4 ' -bipyridyl and derivatives thereof and various electron-rich donors in the aspect of electron donor-acceptor capacity are preliminarily proved. In order to further improve the color change characteristic of the ET type inorganic-organic hybrid color change material, domestic and foreign researchers carry out self-assembly on naphthalene diimide derivatives (NDIs) and tris (pyridyl) -triazines (TPTs) with excellent electron-deficient functional groups and various electron-rich donor carboxylates, phosphates and the like to construct a series of inorganic-organic hybrid photochromic crystalline materials with wide range and quick response. However, the relatively poor reversibility and cycling performance of these electron transfer type inorganic-organic hybrid photochromic systems, etc., become key scientific issues that limit the commercial applications of such materials. This is mainly due to the fact that currently, for realizing the fading process of the electron transfer type photochromic hybrid material, the colored free radicals generated by light induction are oxidized mainly by placing or heating under dark conditions. The electrons in the material are deprived by the oxidation of oxygen in the air, so that the energy band structure in the material is damaged to a certain degree, and the fatigue resistance of the inorganic-organic hybrid material in the color change-color fading cycle process is directly limited. Therefore, the realization of the photo-reversibility of the fading process of the electron donor-acceptor hybrid system and the fatigue resistance of the fading process of the color change become key scientific problems which need to be solved urgently for the performance optimization of the photochromic material, and the core of the method is the matching of the donor-acceptor capacity and the interface relation of the reasonably modulated electron donor and acceptor.
The phenyl diimide derivative has relatively great positive quadrupole moment and relatively high polarizability, and is one kind of organic compound with conjugated pi electron deficiency characteristic and no color. Firstly, by anchoring different functional groups at two ends of an imide ring, the electron accepting capacity can be adjusted within a certain range, so that the electron accepting capacity can be matched with the electron donating-accepting capacities of different electron-rich donors; secondly, the larger pi-electron density is easy to generate different weak interactions (such as lone electron pairs-pi, pi-pi, C-H-pi and the like) with the electron-rich donor, thereby forming various electron transfer channels and realizing the matching of the interface relationship of the electron donor-acceptor hybrid system. Therefore, the benzene diimide with excellent electron deficiency characteristics and the oxygen-containing carboxylic acid electron donor are hybridized through metal coordination, so that the internal electron behavior of the hybrid material can be effectively modulated, the electron donating-accepting capacity and the interface relation matching can be optimized, and the method is an effective strategy for solving the problems of the photoreversibility and the fatigue resistance of the ET type photochromic material.
Disclosure of Invention
The invention overcomes the defects of the prior art and provides a phenyldiimide zinc coordination polymer.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
the phenyldiimide-based zinc coordination polymer has a chemical formula of [ Zn (4-PMPMPMMD) (BTC)]nxDMF, where 4-PMPMMD is N, N-bis (4-pyridylmethyl) -phthalimide, BTC is a carboxylic acid unionized trimesic acid, and DMF is N, N-dimethylformamide; the metallic Zn ion is a 4-coordinated distorted tetrahedral pattern in which two N atomsThe atom is from the 4-PMPMPMMD ligand, and the two O atoms are from the BTC ligand; two 4-PMPMPMMD ligands connect 2 Zn centers through a cis configuration to form a ring structure, then a one-dimensional tubular coordination polymer is formed through the bridging action of BTC, and further a three-dimensional supermolecular framework is formed through the weak interaction of lone electron pairs-pi and pi-pi between BTC and 4-PMPMMD, and the structure is as follows:
furthermore, the excellent electron-deficient acceptor phenylimide of the phenylimide-based zinc coordination polymer is hybridized with the oxygen-containing carboxylic acid electron donor through the coordination of metal zinc, so that a specific interface relation between an electron donor and an electron acceptor is formed.
Further, the phenyl diimide-based zinc coordination polymer is a color-changing material based on intermolecular electron transfer.
Further, the crystals of the phenyldiimide based zinc coordination polymer were measured by SMART APEX CCD single crystal diffractometer using a graphite monochromator for Mo-Ka radiation
Collecting data in an omega scanning mode, carrying out Lp factor correction and SADABS program absorption correction, analyzing a structure, determining the position of a heavy atom by using a direct method, then solving the coordinate of the non-hydrogen atom by using a difference function method and a least square method, obtaining the position of the hydrogen atom by using a theoretical hydrogenation method, correcting the structure by using the least square method, and enabling all the non-hydrogen atoms to be anisotropic; all calculation work is completed by using an Olex2-1.3 program; the crystallographic parameters were measured as follows: molecular weight of 670.85, belonging to triclinic system, space group P-1, unit cell parameter
α(°)＝79.260(2)，β(°)＝72.368(3)，γ(°)＝71.339(2)，
Z＝2。
The invention also provides a preparation method of the phenyldiimide zinc coordination polymer, which comprises the following steps:
1) 4-PMPMPMMD, Zn (NO)3)2And trimesic acid are stirred in a hot DMF solution with the volume of 5mL according to the molar ratio of 1: 3-10: 2-3 until colorless transparent clear liquid is obtained;
2) placing the solution obtained in the step 1) at room temperature in a dark condition for reacting for 1-3 days, separating out crystals, washing with DMF, filtering, and drying to obtain colorless transparent blocky crystals;
3) or transferring the solution in the step (1) to a reaction kettle, placing the reaction kettle in an oven at the temperature of 60-110 ℃ for reaction for 1-5 days, cooling to room temperature after the reaction is finished, generating crystals, washing with DMF, filtering, and drying to obtain colorless transparent blocky crystals.
The synthesis method comprises a room-temperature solvent volatilization method and a solvothermal reaction method.
In addition, the invention also provides application of the phenyldiimide zinc coordination polymer or as a photochromic material with ultra-fast light reversibility and ultra-strong fatigue resistance.
Further, the photochromic material has ultra-fast photo-reversibility during fading and ultra-strong fatigue resistance during a color change-fading cycle.
Compared with the prior art, the invention has the following beneficial effects:
(1) according to the invention, the benzene diimide with excellent electron deficiency is taken as an electron acceptor, and is hybridized with the oxygen-containing carboxylic acid electron donor through the coordination effect of metal zinc, so that the photochromic material with ultrafast photo-reversibility and super-strong fatigue resistance of the benzene diimide-based zinc coordination polymer is provided, the new functions of ultrafast photo-reversibility in the fading process of the ET-type electrons and hybrid and super-strong fatigue resistance in the color changing-fading cycle process are provided, the excellent color changing characteristic of the existing ET photochromic hybrid material is provided, and the blank in the technical field is filled.
(2) The intermolecular ET mechanism-based color-changing material provided by the invention can be subjected to color change under ultraviolet irradiation and color change under visible light irradiation, and a crystalline material with ultra-high fatigue resistance in a color change-color change cycle process is obtained, so that the application range of the color-changing material is greatly expanded.
(3) The preparation method of the organic-inorganic hybrid color-changing material provided by the invention is simple and easy to implement.
Drawings
FIG. 1 is a diagram showing asymmetric structural units of a phenylimide-based zinc coordination polymer of the present invention.
FIG. 2 shows a ring formed by a ligand and a zinc metal ion in the phenylimide-based zinc coordination polymer according to the present invention.
FIG. 3 is a structural diagram of a one-dimensional tubular coordination chain formed by a phenylimidoyl zinc coordination polymer according to the present invention.
FIG. 4 is a schematic representation of the dimensions of a one-dimensional tube formed from the phenylimide-based zinc coordination polymer of the present invention.
FIG. 5 is a schematic diagram showing the stacking of the phenylimide-based zinc coordination polymer of the present invention.
FIG. 6 is a graph showing the relationship between donor-acceptor interfaces of the phenylimidoyl zinc coordination polymer of the present invention.
FIG. 7 is a thermogravimetric-differential thermal profile of a phenylimidoyl zinc coordination polymer of the present invention.
FIG. 8 is a color change diagram under ultraviolet light and a color fading diagram under visible light of the phenylimide-based zinc coordination polymer of the present invention.
FIG. 9 is a chart showing infrared absorption spectra before and after photochromism of the phenylimide-based zinc coordination polymer of the present invention.
FIG. 10 is an X-ray powder diffraction pattern of a phthalimide-based zinc coordination polymer of the present invention before and after photochromism.
FIG. 11 is a graph of the time dependent UV-VIS absorption spectrum of a phenylimide-based zinc coordination polymer of the present invention during color change.
FIG. 12 is a graph of the time dependent UV-VIS absorption spectrum of a phenylimide-based zinc coordination polymer of the present invention during visible light fading.
FIG. 13 is an electron paramagnetic resonance image of a phthalimide-based zinc coordination polymer before and after photochromism in accordance with the present invention.
FIG. 14 is a cycle chart showing 160 cycles before and after photochromism of the phenylimide-based zinc coordination polymer of the present invention.
FIG. 15 is an X-ray powder diffraction pattern of 160 cycles before and after photochromism of the phenylimide-based zinc coordination polymer of the present invention.
Detailed Description
The present invention is further illustrated by the following specific examples.
Example 1
Weighing 4-PMPMPMPMMD (20mg, 0.05mmol) in a beaker, adding 5mL DMF solution, heating and stirring to clarify, adding Zn (NO)3)2(28mg, 0.15mmol) and trimesic acid (21mg, 0.1mmol) were stirred for 10 minutes to give a colorless transparent clear solution. Standing at room temperature in the dark for 2-3 days to obtain colorless transparent bulk crystal, washing with DMF, filtering and drying. Yield: 41.6% (based on 4-PMPMPMMD).
Example 2
4-PMPMPMMD (20mg, 0.05mmol) was weighed into a beaker, 5mL DMF solution was added, heated to stir until clear, and Zn (NO) was added3)2(57mg, 0.3mmol) and trimesic acid (21mg, 0.1mmol) were stirred for 10 minutes to give a colorless transparent clear solution. Standing at room temperature in the dark for 2-3 days to obtain colorless transparent bulk crystal, washing with DMF, filtering and drying. Yield: 50.4% (based on 4-PMPMPMMD).
Example 3
4-PMPMPMMD (20mg, 0.05mmol) was weighed into a beaker, 5mL DMF solution was added, heated to stir until clear, and Zn (NO) was added3)2(95mg, 0.5mmol) and trimesic acid (32mg, 0.15mmol) were stirred for 10 minutes to give a colorless clear solution. Standing at room temperature in the dark for 2-3 days to obtain colorless transparent bulk crystal, washing with DMF, filtering and drying. Yield: 62.3% (based on 4-PMPMPMMD).
Example 4
4-PMPMPMD (20mg,0.05mmol) was placed in a beaker, 5mL of DMF solution was added, heated and stirred until clear, and Zn (NO) was added3)2(28mg, 0.15mmol) and trimesic acid (21mg, 0.1mmol) were stirred for 10 minutes to give a colorless transparent clear solution. The solution was transferred to a 15mL reaction kettle, reacted in an oven at 60 ℃ for 3 days, cooled to room temperature to give colorless transparent bulk crystals, washed with DMF, filtered and dried. Yield: 45.9% (based on 4-PMPMPMMD).
Example 5
4-PMPMPMMD (20mg, 0.05mmol) was weighed into a beaker, 5mL DMF solution was added, heated to stir until clear, and Zn (NO) was added3)2(28mg, 0.15mmol) and trimesic acid (21mg, 0.1mmol) were stirred for 10 minutes to give a colorless transparent clear solution. The solution was transferred to a 15mL reaction kettle, reacted in a 95 ℃ oven for 3 days, cooled to room temperature to give colorless transparent bulk crystals, washed with DMF, filtered and dried. Yield: 43.7% (based on 4-PMPMPMMD).
Example 6
4-PMPMPMMD (20mg, 0.05mmol) was weighed into a beaker, 5mL DMF solution was added, heated to stir until clear, and Zn (NO) was added3)2(28mg, 0.15mmol) and trimesic acid (21mg, 0.1mmol) were stirred for 10 minutes to give a colorless transparent clear solution. The solution was transferred to a 15mL reaction kettle, reacted in a 110 ℃ oven for 3 days, cooled to room temperature to give colorless transparent bulk crystals, washed with DMF, filtered and dried. Yield: 42.1% (based on 4-PMPMPMMD).
Example 7 photochromic experiments
Photochromic experiments: A300W ultraviolet high-pressure mercury lamp (365 nm) is selected, a sample is placed on a glass sheet and placed on a constant-temperature metal plate which is 30cm away from a light source, the sample changes color for 1s after being irradiated by ultraviolet rays, the color is changed from colorless to bright yellow, the color is gradually deepened along with the increase of illumination time, and finally the color is changed to orange. Saturation was reached at 1min and the sample after light was represented as compound 1 and 1P. The color of the sample was hardly changed by keeping it in the dark for 2 months or heating it at a temperature of 140 ℃. But under the irradiation of visible light (more than or equal to 420nm), the sample can completely fade back to a colorless state within 2 min. The reversible change can be cycled at least 160 times, which is confirmed by ultraviolet-visible absorption spectrum, and the reversible change has good structural integrity, is not damaged and has super fatigue resistance stability.
Example 8
The crystal structure of compound 1 obtained in example 1 was determined as follows: selecting crystals suitable for data acquisition by a single crystal X-ray diffractometer under a microscope. The single crystal of appropriate size is subjected to X-ray single crystal structural analysis. The X-ray diffraction data of the crystal is measured by SMART APEX CCD single crystal diffractometer and Mo-Kalpha radiation is performed by a graphite monochromator
Data were collected in the ω -scan mode and Lp factor correction and SADABS program absorption correction were performed. The position of a heavy atom is determined by using a direct method, then the coordinates of the non-hydrogen atom are obtained by using a difference function method and a least square method, the position of the hydrogen atom is obtained by using a theoretical hydrogenation method, and the structure is corrected by using the least square method, so that all the non-hydrogen atoms are anisotropic. All computational work was done using the Olex2-1.3 program. The main crystallographic data of the compounds are shown in table 1.
TABLE 1 crystallographic structural parameters of Benzimidinium zinc coordination polymers
Claims (7)
1. The phenyldiimide-based zinc coordination polymer has a chemical formula of [ Zn (4-PMPMPMMD) (BTC)]nxDMF, wherein 4-PMPMMD isN, NBis (4-pyridylmethyl) -phenyldiimide, BTC is a carboxylic acid unionized trimesic acid, DMF isN, N-dimethylformamide; the metallic Zn ion is a 4-coordinated distorted tetrahedral pattern, in which two N atoms are derived from 4-PMPMPMD ligands and two O atoms are derived from BTC ligands(ii) a Two 4-PMPMPMMD ligands connect 2 Zn centers through a cis configuration to form a ring structure, then a one-dimensional tubular coordination polymer is formed through the bridging action of BTC, and further a three-dimensional supermolecular framework is formed through the weak interaction of lone electron pairs-pi and pi-pi between BTC and 4-PMPMMD, and the structure is as follows:
2. the phenyldiimide-based zinc coordination polymer according to claim 1, wherein the excellent electron deficient acceptor phenyldiimide of the phenyldiimide-based zinc coordination polymer is hybridized with the oxygen-containing carboxylic acid electron donor through coordination of metallic zinc, so as to form a specific interface relationship between the electron donor and the electron acceptor.
3. The phenyldiimide based zinc coordination polymer according to claim 1, wherein said phenyldiimide based zinc coordination polymer is a color-changing material based on intermolecular electron transfer.
4. The phenyldiimide based zinc coordination polymer according to claim 1, wherein the crystals of the phenyldiimide based zinc coordination polymer are measured by a SMART APEX CCD single crystal diffractometer, data are collected in an ω scanning manner using a graphite monochromator Mo-K α radiation λ = 0.71073, Lp factor correction and SADABS procedure absorption correction are performed, the position of heavy atoms is determined by analyzing the structure using a direct method, then the coordinates of non-hydrogen atoms are determined by a difference function method and a least square method, and the positions of hydrogen atoms are obtained by a theoretical hydrogenation method, the structure is corrected by a least square method, all non-hydrogen atoms are anisotropic; all calculation work is completed by using an Olex2-1.3 program; the crystallographic parameters were measured as follows: has a molecular weight of 670.85, belongs to triclinic system and space groupP-1, unit cell parametera (Å)= 10.1573(6)，b (Å) = 15.5108(9)，c(Å) = 16.1174(9)，α (°) = 79.260(2)，β(°) = 72.368(3)，γ (°) = 71.339(2)，V (Å3) = 2281.5(2)，Z = 2。
5. The preparation method of the phenyldiimide zinc coordination polymer is characterized by comprising the following steps:
1) 4-PMPMPMMD, Zn (NO)3)2And trimesic acid are stirred in a hot DMF solution with the volume of 5mL according to the molar ratio of 1: 3-10: 2-3 until colorless transparent clear liquid is obtained;
2) placing the solution obtained in the step 1) at room temperature in a dark condition for reacting for 1-3 days, separating out crystals, washing with DMF, filtering, and drying to obtain colorless transparent blocky crystals;
3) or transferring the solution in the step (1) to a reaction kettle, placing the reaction kettle in an oven at the temperature of 60-110 ℃ for reaction for 1-5 days, cooling to room temperature after the reaction is finished, generating crystals, washing with DMF, filtering, and drying to obtain colorless transparent blocky crystals.
6. Use of the phenyldiimide based zinc complex polymer according to any one of claims 1 to 4 or the phenyldiimide based zinc complex polymer prepared by the preparation method according to claim 5 as a photochromic material having ultra-fast photo-reversibility and ultra-high fatigue resistance.
7. The use according to claim 6, wherein said photochromic material has ultra-fast photo-reversibility during bleaching and superior fatigue resistance during the discolouration-bleaching cycle.
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