CN114479830B - Organic eutectic@rare earth complex core-shell structure with dual light emission characteristics - Google Patents
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Abstract
The invention relates to an organic eutectic@rare earth complex core-shell structure with dual light emission characteristics and a preparation method thereof, wherein the core-shell structure comprises a eutectic core and a rare earth complex shell; the organic co-crystal core comprises a co-crystal main body molecule coordinated with rare earth ions and a co-crystal acceptor molecule assembled with the co-crystal main body molecule through hydrogen bonds; the rare earth complex shell is a rare earth complex formed in the surface lattice region of the eutectic by coordinating trivalent rare earth ions with host molecules in the surface lattice of the eutectic by an epitaxial coordination growth method. The core-shell structure prepared by the invention has the dual light emission characteristics of adjustable light emission eutectic and long-service-life rare earth ions; the first attempt is to compound the organic eutectic with rare earth ions, and introduce the luminescence of the rare earth ions into the system on the premise of keeping the light emission of the organic eutectic, so as to realize the energy transfer of the organic eutectic system.
Description
Technical Field
The invention belongs to the technical field of luminescent materials, and particularly relates to an organic eutectic@rare earth complex core-shell structure luminescent material and a preparation method thereof.
Background
Organic heterojunction not only exhibits heterostructure characteristics inherent to organic semiconductors, such as rectifying behavior and photovoltaic effect. Meanwhile, the self-assembly optical fiber has the advantages of controllable self-assembly behavior, excellent tunable optical characteristics, large-area compounding and integration, low processing cost and the like. The organic light-emitting diode has important application value in the fields of organic photoelectric detectors, organic field effect transistors, organic solar cells, optoelectronics and the like.
At present, a core-shell heterostructure constructed by taking an organic eutectic as a precursor is attracting attention. The assembling, splicing and modifying of the eutectic are realized by combining a chemical method with a crystal engineering technology, so that the heterogeneous morphology of the eutectic is controlled and the optical characteristics of the module are changed. The hetero-crystalline with the co-crystal nucleus shell not only integrates multiple photoelectric functions of an organic material, but also derives novel and diverse hetero-structure optical properties, such as controllable multiple light emission, controllable light output, optical logic gate operation, heterogeneous light emission, optical modulation, optical information storage, multicolor laser display, biological application design, optical waveguide and the like.
The hybridization and heterogeneity of the organic eutectic material are key to preparing a eutectic core-shell heterostructure with energy transfer characteristics. However, the eutectic is formed by orderly and closely stacking host and guest molecules through supermolecular hydrogen bonding, and the lattice, stacking structure and energy matching not only limit the hybridization of donor/acceptor molecules, but also inhibit the doping and assembly of rare earth ions in a eutectic system based on energy transfer luminescence. Based on the above, if the organic eutectic and the rare earth ions are compounded, the luminescence of the rare earth ions is introduced into the system on the premise of keeping the light emission of the organic eutectic, so that the method is a new attempt and is also a new way for realizing the energy transfer of the organic eutectic system.
Disclosure of Invention
The invention aims to provide an organic eutectic@rare earth complex core-shell structure with double light emission characteristics, and also provides a preparation method of the eutectic rare earth complex core-shell structure with double light emission characteristics, so as to solve the problem that the prepared core-shell structure has the double light emission characteristics of adjustable light emission eutectic and long-service-life rare earth ions.
The invention aims at realizing the following technical scheme:
an organic eutectic@rare earth complex core-shell structure with dual light emission characteristics comprises an organic eutectic core and a rare earth complex shell;
the organic eutectic core comprises a eutectic donor molecule coordinated with rare earth ions and a eutectic acceptor molecule assembled by hydrogen bonds with the eutectic donor molecule;
the rare earth complex shell is a rare earth complex formed in the lattice area of the surface of the eutectic by coordinating rare earth ions with donor molecules in the lattice of the surface of the organic eutectic through an epitaxial coordination growth method.
Further, the co-crystal donor molecule comprises one or more of phenanthroline, dipyridine, terpyridine and derivatives thereof.
Further, the co-crystal acceptor molecule includes one or two of 1,2,4, 5-tetracyanobenzene, 1, 4-dicyanobenzene, tetrafluoroterephthalonitrile, isophthalonitrile, 1,3, 5-tricyanobenzene, 3,4,5, 6-tetrafluorophthalonitrile, 1, 4-diiodotetrafluorobenzene, 1,3, 5-trifluoro-2, 4, 6-triiodobenzene, and 1, 2-diiodotetrafluorobenzene.
Further, the rare earth ions comprise one or more of trivalent europium ions, trivalent terbium ions, trivalent dysprosium ions, trivalent erbium ions and trivalent samarium ions.
The preparation method of the organic eutectic@rare earth complex core-shell structure with the dual light emission characteristics comprises the following steps:
and (3) dripping a solution containing one or more rare earth ions with a certain concentration on the surface of the eutectic, and carrying out heat treatment to coordinate the rare earth ions with donor molecules in a crystal lattice on the surface of the eutectic, so that a white rare earth complex grows on the surface of the organic eutectic to form a rare earth complex crystal shell, and thus the core-shell structure of the organic eutectic and the rare earth complex is obtained.
The preparation method of the eutectic rare earth complex core-shell structure with the dual light emission characteristic comprises the following steps:
a. dissolving a eutectic donor molecule and a eutectic acceptor molecule in acetonitrile solution according to a ratio of 1:1, and preparing a single eutectic by a method of slowly volatilizing a solvent;
b. c, placing the single eutectic obtained in the step a on a heating table for heat treatment, dripping ethanol solution containing one or more rare earth ions on the surface of the heat-treated eutectic, and coating a layer of white rare earth ion complex on the surface of the eutectic to obtain the core-shell structure of the organic eutectic and the rare earth complex.
Further, in the step b, the heating temperature of the heating table is 50 ℃, and the heat treatment time is 1 minute.
Further, in the step b, the rare earth ions comprise one or more of europium trivalent europium ions, terbium trivalent ions, dysprosium trivalent ions, erbium trivalent ions and samarium trivalent ions.
Compared with the prior art, the invention has the beneficial effects that:
the core-shell structure prepared by the invention has the dual light emission characteristics of adjustable light emission eutectic and long-service-life rare earth ions; the first attempt is to compound the organic eutectic with rare earth ions, and introduce the luminescence of the rare earth ions into the system on the premise of keeping the light emission of the organic eutectic, so as to realize the energy transfer of the organic eutectic system.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings that are needed in the embodiments will be briefly described below, it being understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and other related drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1A is an SEM photograph of a terpyridine-1, 2-diiodotetrafluorobenzene (Tpy-1, 2-DITFB) organic co-crystal;
FIG. 1 SEM image of Tpy-1,2-DITFB@Eu-Tpy core-shell structure;
FIG. 2A EDX spectrum of Tpy-1,2-DITFB organic co-crystals;
FIG. 2B EDX spectrum of Tpy-1,2-DITFB@Eu-Tpy core-shell structure;
FIG. 3 is a photograph of a fluorescence image of ATpy-1,2-DITFB organic co-crystal under UV light;
FIG. 3B is a photograph of a fluorescent image of a Tpy-1,2-DITFB@Eu Tpy core-shell structure under ultraviolet light irradiation;
FIG. 4 is a light emission fluorescence spectrum of ATpy-1,2-DITFB organic co-crystal;
FIG. 4B is a dual light emission fluorescence spectrum of a Tpy-1,2-DITFB@Eu-Tpy core-shell structure;
FIG. 5A is an SEM photograph of A1 phenanthroline-1, 2,4, 5-tetracyanophene (Phen-TCNB) organic co-crystal; FIG. 5A2 EDX spectrum of phenanthroline-1, 2,4, 5-tetracyanophene (Phen-TCNB) organic co-crystal; FIG. 5B1 SEM photograph of Phen-TCNB@Eu-Phen core-shell structure;
FIG. 5B2 Phen-TCNB@Eu-Phen core-shell structure EDX energy spectrum;
FIG. 5 is a SEM photograph of a core-shell structure of a C1 Phen-TCNB@Tb-Phen complex;
FIG. 5 is an EDX spectrum of a core-shell structure of a C2 Phen-TCNB@Tb-Phen complex;
FIG. 6A1 Phen-TCNB organic eutectic fluorescence imaging;
FIG. 6A2 Phen-TCNB organic eutectic fluorescence spectrum;
FIG. 6B1 fluorescence imaging of Phen-TCNB@Eu-Phen core-shell structure;
FIG. 6B2 Phen-TCNB@Eu-Phen core-shell structure fluorescence spectrum;
FIG. 6 fluorescence imaging of a C1 Phen-TCNB@Tb-Phen core-shell structure;
FIG. 6 fluorescence spectrum of C2 Phen-TCNB@Tb-Phen core-shell structure.
Detailed Description
The present invention will be further described with reference to specific examples, which are given in detail on the basis of the present technology, but the scope of the present invention is not limited to the following examples.
A eutectic rare earth complex core-shell structure with dual light emission characteristics comprises a eutectic core and a rare earth complex shell; the eutectic core comprises a eutectic donor molecule coordinated with rare earth ions and a eutectic acceptor molecule assembled by hydrogen bonds with the eutectic donor molecule; the rare earth complex crystal shell is a rare earth complex formed in a lattice area on the surface of the eutectic by coordinating rare earth ions with donor molecules in the lattice on the surface of the eutectic through an epitaxial coordination growth method.
Specifically, the co-crystal donor molecule comprises one or more of phenanthroline, dipyridine, terpyridine and derivatives thereof. The co-crystal acceptor molecule comprises one or two of 1,2,4, 5-tetracyanobenzene, 1, 4-dicyanobenzene, tetrafluoroterephthalonitrile, isophthalonitrile, 1,3, 5-tricyanobenzene, 3,4,5, 6-tetrafluorophthalonitrile, 1, 4-diiodotetrafluorobenzene, 1,3, 5-trifluoro-2, 4, 6-triiodobenzene and 1, 2-diiodotetrafluorobenzene. The rare earth ions comprise one or more of trivalent europium ions, trivalent terbium ions, trivalent dysprosium ions, trivalent erbium ions and trivalent samarium ions.
The preparation method of the organic eutectic@rare earth complex core-shell structure with double light emission characteristics comprises the following steps: and (3) dripping a solution containing one or more rare earth ions at a certain concentration on the surface of the eutectic, and carrying out heat treatment to coordinate the rare earth ions with donor molecules in a crystal lattice on the surface of the eutectic, so that a white rare earth complex grows on the surface of the organic eutectic to form a rare earth complex shell, thereby obtaining the organic eutectic@rare earth complex core-shell structure. The method specifically comprises the following steps:
a. dissolving a eutectic donor molecule and a eutectic acceptor molecule in acetonitrile solution according to a ratio of 1:1, and preparing a single organic eutectic by a method of slowly volatilizing a solvent;
b. c, placing the single organic eutectic obtained in the step a on a heating table at 50 ℃ for heat treatment for 1 minute, dripping ethanol solution containing one or more rare earth ions on the surface of the heat-treated eutectic, and coating a layer of white rare earth ion complex on the surface of the eutectic to obtain the organic eutectic@rare earth complex core-shell structure. The rare earth ions comprise one or more of trivalent europium ions, trivalent terbium ions, trivalent dysprosium ions, trivalent erbium ions and trivalent samarium ions.
Example 1
a. And (3) taking terpyridine (Tpy) as a co-crystal donor molecule, taking 1, 2-diiodotetrafluorobenzene (1, 2-DITFB) as a co-crystal acceptor molecule, dissolving the co-crystal acceptor molecule in acetonitrile solution according to a ratio of 1:1, and obtaining the Tpy-1,2-DITFB co-crystal by a method of slowly volatilizing a solvent.
b. Placing the single eutectic obtained in the step a on a heating table at 50 ℃ for heat treatment for 1 min, and adding 20 mu L of EuCl 3 And (3) dripping the ethanol solution on the heat-treated eutectic surface, and coating a layer of white rare earth ion complex on the eutectic surface to obtain a Tpy-1,2-DITFB@Eu-Tpy core-shell structure.
The morphology of the eutectic, organic eutectic@rare earth complex core-shell structure obtained in example 1 was observed by using a scanning electron microscope SEM. As shown in FIG. 1A, it can be observed that the Tpy-TFP eutectic surface is flat, while the core-shell structure surface is smooth, as shown in FIG. 1. The co-crystal, organic co-crystal and rare earth complex core-shell obtained in example 1 was subjected to X-ray spectroscopy (EDX)The surface composition of the structure is characterized. The C and N elements can be identified in the eutectic EDX spectrum as shown in figure 2A, and C, N and Eu can be identified in the EDX spectrum of the core-shell structure 3+ The elements are shown in fig. 2B.
Example 2
The core-shell structure obtained in example 1 was subjected to fluorescence spectroscopy.
Fluorescence imaging of the eutectic and organic eutectic @ rare earth complex core-shell structure obtained in example 1 was observed using a fluorescence microscope. The ultraviolet light with 365nm wavelength irradiates the single eutectic and the core-shell structure, and synchronously collects fluorescence imaging and fluorescence spectrum. As shown in FIG. 3A, the Tpy-TFP eutectic can be observed to exhibit green fluorescence, and the fluorescence band of the organic eutectic is between 500 and 700nm, as shown in FIG. 4A. The Tpy-1,2-DITFB@Eu-Tpy core-shell structure presents red fluorescence, and as shown in FIG. 3B, fluorescence characteristic peaks of trivalent europium ions at 595, 612, 623 and 702nm are respectively attributed to 5 D 0 → 7 F 1 、 5 D 0 → 7 F 2 、 5 D 0 → 7 F 3 A kind of electronic device with high-pressure air-conditioning system 5 D 0 → 7 F 4 As shown in fig. 4B.
Example 3
The preparation method of the organic eutectic@rare earth complex core-shell structure with double light emission characteristics comprises the following steps:
a. o-phenanthroline (Phen) is taken as a co-crystal donor molecule, 1,2,4, 5-Tetracyanophene (TCNB) is taken as a co-crystal acceptor molecule, the co-crystal acceptor molecule is dissolved in acetonitrile solution according to a ratio of 1:1, and Phen-TCNB eutectic is obtained by a method of slowly volatilizing a solvent.
Placing the single eutectic obtained in step a on a heating table at 50deg.C for heat treatment for 1 min, and respectively adding 10 μLEuCl 3 Ethanol solution and 10. Mu.L TbCl 3 And (3) dripping the ethanol solution on the heat-treated eutectic surface, and coating a layer of white rare earth ion complex on the eutectic surface to obtain Phen-TCNB@Eu-Phen and Phen-TCNB@Tb-Phen core-shell structures respectively.
The eutectic, organic eutectic and rare earth complex core-shell obtained in example 3 was subjected to SEMAnd observing the morphology of the structure. As shown in FIG. 5A1, a leveling of the Tpy-TFP eutectic surface can be observed. The surface of the core-shell structure is smooth, as shown in fig. 5B1 and fig. 5C 1. The surface composition of the eutectic and organic eutectic @ rare earth complex core-shell structure obtained in example 3 was characterized by X-ray spectroscopy (EDX). The C and N elements can be identified in the EDX spectrum of the eutectic, and C, N and Eu can be identified in the EDX spectrum of the Phen-TCNB@Eu-Phen core-shell structure as shown in FIG. 5A2 3+ Elements, as shown in fig. 5B 2. C, N and Tb can be identified in EDX spectrum of Phen-TCNB@Tb-Phen core-shell structure 3+ Elements, as shown in fig. 5C 2.
Example 4
The core-shell structure obtained in example 3 was subjected to fluorescence spectroscopy.
Fluorescence imaging of the eutectic and organic eutectic @ rare earth complex core-shell structure obtained in example 3 was observed using a fluorescence microscope. The ultraviolet light with 365nm wavelength irradiates the single eutectic and the core-shell structure, and synchronously collects fluorescence imaging and fluorescence spectrum. As shown in FIG. 6A1, it was observed that Phen-TCNB co-crystals exhibited blue fluorescence, and that a broad fluorescence band of the organic co-crystals existed between 400 and 600nm, as shown in FIG. 6A 2. Phen-TCNB@Eu-Phen core-shell structure presents red fluorescence, as shown in FIG. 6B1, fluorescence characteristic peaks of trivalent europium ions at 595, 612 and 702nm, as shown in FIG. 6B2, respectively belonging to trivalent europium ions 5 D 0 → 7 F 1 、 5 D 0 → 7 F 2 A kind of electronic device with high-pressure air-conditioning system 5 D 0 → 7 F 4 And (5) transition. Phen-TCNB@Tb-Phen core-shell structure presents green fluorescence, and as shown in FIG. 6C1, fluorescence characteristic peaks of trivalent terbium ions at 491, 544, 584 and 621nm are respectively attributed to terbium ions 5 D 4 → 7 F 6 、 5 D 4 → 7 F 5 、 5 D 4 → 7 F 3 A kind of electronic device with high-pressure air-conditioning system 5 D 4 → 7 F 3 The electron transitions as shown in fig. 6C 2.
Note that the above is only a preferred embodiment of the present invention and the technical principle applied. It will be understood by those skilled in the art that the present invention is not limited to the particular embodiments described herein, but is capable of various obvious changes, rearrangements and substitutions as will now become apparent to those skilled in the art without departing from the scope of the invention. Therefore, while the invention has been described in connection with the above embodiments, the invention is not limited to the embodiments, but may be embodied in many other equivalent forms without departing from the spirit or scope of the invention, which is set forth in the following claims.
Claims (5)
1. An organic eutectic@rare earth complex core-shell structure with dual light emission characteristics is characterized in that: comprises an organic eutectic core and a rare earth complex shell;
the organic eutectic core comprises eutectic donor molecules coordinated with rare earth ions and eutectic acceptor molecules assembled by hydrogen bonds with the eutectic donor molecules;
the rare earth complex shell is a rare earth complex formed in the surface area of the eutectic by coordinating trivalent rare earth ions with main molecules in the surface crystal lattice of the organic eutectic through an epitaxial coordination growth method;
the co-crystal donor molecule comprises one or more of phenanthroline, dipyridine and terpyridine;
the co-crystal acceptor molecule comprises one or two of 1,2,4, 5-tetracyanobenzene, 1, 4-dicyanobenzene, tetrafluoroterephthalonitrile, isophthalonitrile, 1,3, 5-tricyanobenzene, 3,4,5, 6-tetrafluorophthalonitrile, 1, 4-diiodotetrafluorobenzene, 1,3, 5-trifluoro-2, 4, 6-triiodobenzene and 1, 2-diiodotetrafluoro.
2. The organic eutectic @ rare earth complex core-shell structure with dual light emission characteristics according to claim 1, wherein: the rare earth ions comprise one or more of trivalent europium ions, trivalent terbium ions, trivalent dysprosium ions, trivalent erbium ions and trivalent samarium ions.
3. The method for preparing the organic eutectic @ rare earth complex core-shell structure with dual light emission characteristics according to claim 1, comprising the following steps:
dropping a solution containing one or more rare earth ions with a certain concentration on the surface of the eutectic, and carrying out heat treatment to coordinate the rare earth ions with donor molecules in a crystal lattice on the surface of the eutectic, so that a white rare earth complex grows on the surface of the organic eutectic to form a rare earth complex crystal shell, and obtaining an organic eutectic@rare earth complex core-shell structure;
the preparation method of the organic eutectic@rare earth complex core-shell structure with the dual light emission characteristic comprises the following steps:
a. the donor molecule and the co-crystal acceptor molecule of the co-crystal are dissolved in acetonitrile solution according to the proportion of 1:1, and a single organic co-crystal is prepared by a method of slowly volatilizing the solvent;
b. c, placing the single organic eutectic obtained in the step a on a heating table for heat treatment, dripping ethanol solution containing one or more rare earth ions on the surface of the heat-treated eutectic, and coating a layer of white rare earth ion complex on the surface of the eutectic to obtain the core-shell structure of the organic eutectic and the rare earth complex.
4. The method for preparing the organic eutectic @ rare earth complex core-shell structure with dual light emission characteristics according to claim 3, wherein the method comprises the following steps: and b, heating the heating table to 50 ℃ and performing heat treatment for 1 minute.
5. The method for preparing the organic eutectic @ rare earth complex core-shell structure with dual light emission characteristics according to claim 3, wherein the method comprises the following steps: and b, the rare earth ions comprise one or more of europium ions, terbium ions, dysprosium ions, erbium ions and samarium ions.
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