CN114479830A - Organic eutectic @ rare earth complex core-shell structure with dual light emission characteristics - Google Patents

Organic eutectic @ rare earth complex core-shell structure with dual light emission characteristics Download PDF

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CN114479830A
CN114479830A CN202111648230.5A CN202111648230A CN114479830A CN 114479830 A CN114479830 A CN 114479830A CN 202111648230 A CN202111648230 A CN 202111648230A CN 114479830 A CN114479830 A CN 114479830A
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eutectic
rare earth
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CN114479830B (en
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王晶
陈雷
薛向欣
赵丽娜
徐娜
孙艳涛
王丽
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Jilin Normal University
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Abstract

The invention relates to an organic eutectic @ rare earth complex core-shell structure with double light emission characteristics and a preparation method thereof, wherein the core-shell structure comprises an eutectic core and a rare earth complex shell; the organic eutectic inner core comprises eutectic main molecules which are coordinated with rare earth ions and eutectic receptor molecules which are assembled with the eutectic main molecules through hydrogen bonds; the rare earth complex shell is a rare earth complex formed in a surface lattice region of a eutectic by coordinating trivalent rare earth ions with host molecules in the surface lattice of the eutectic through an epitaxial coordination growth method. The core-shell structure prepared by the invention has the characteristics of adjustable light emission eutectic and dual light emission of long-life rare earth ions; the organic eutectic is compounded with the rare earth ions for the first time, and on the premise of keeping the light emission of the organic eutectic, the light emission of the rare earth ions is introduced into the system, so that the energy transfer of the organic eutectic system is realized.

Description

Organic eutectic @ rare earth complex core-shell structure with dual light emission characteristics
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 heterojunctions exhibit not only the heterostructure properties inherent to organic semiconductors, such as rectifying behavior and photovoltaic effect. Meanwhile, the tunable optical fiber has the advantages of controllable self-assembly behavior, tunable excellent optical characteristics, large-area compounding and integration, low processing cost and the like. The method has important application value in the fields of organic photoelectric detectors, organic field effect transistors, organic solar cells, optoelectronics and the like.
At present, the core-shell heterostructure constructed by taking organic eutectic crystals as precursors is receiving much attention. The eutectic is assembled, spliced and modified 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 eutectic core-shell heterogeneous crystal not only integrates multiple photoelectric functions of organic materials, but also derives novel and various heterogeneous structure optical properties, such as adjustable and 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 the heterogeneity of the organic eutectic material are the key points for preparing the eutectic core-shell heterostructure with the energy transfer characteristic. However, the eutectic is formed by orderly and tightly packing host-guest molecules through the action of supermolecule hydrogen bonds, and the crystal lattice, the packing structure and the energy matching not only limit the hybridization of donor/acceptor molecules, but also inhibit the doping and assembly of rare earth ions in the eutectic system based on energy transfer luminescence. Based on the method, if the organic eutectic and the rare earth ions can be compounded, on the premise of keeping the light emission of the organic eutectic, the luminescence of the rare earth ions is introduced into the system, so that the method is a new attempt and 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 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 double light emission characteristics of adjustable light emission eutectic and long-life rare earth ions.
The purpose of the invention is realized by the following technical scheme:
an organic eutectic @ rare earth complex core-shell structure with double light emission characteristics comprises an organic eutectic core and a rare earth complex shell;
the organic eutectic kernel comprises eutectic main molecules which are coordinated with rare earth ions and eutectic acceptor molecules which are assembled with the eutectic main molecules through hydrogen bonds;
the rare earth complex shell is a rare earth complex formed in a surface lattice region of the organic eutectic by coordinating rare earth ions with host molecules in the surface lattice of the eutectic through an epitaxial coordination growth method.
Further, the co-crystal donor molecule comprises one or more of phenanthroline, bipyridine, 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 include one or more of trivalent europium ions, trivalent terbium ions, trivalent dysprosium ions, trivalent erbium ions and trivalent samarium ions.
A preparation method of an organic eutectic @ rare earth complex core-shell structure with dual light emission characteristics comprises the following steps:
dropping a solution containing one or more rare earth ions with a certain concentration on the surface of the eutectic, performing heat treatment to ensure that the rare earth ions are coordinated with donor molecules in the surface crystal lattice of the eutectic, and growing a white rare earth complex on the surface of the organic eutectic to form a rare earth complex crystal shell, thereby obtaining the core-shell structure of the organic eutectic and the rare earth complex.
The preparation method of the eutectic rare earth complex core-shell structure with the dual light emission characteristic specifically comprises the following steps:
a. dissolving a co-crystal host molecule and a co-crystal guest molecule in acetonitrile solution according to the proportion of 1:1, and preparing a single co-crystal by a method of slowly volatilizing a solvent;
b. and 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 eutectic subjected to heat treatment, 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 step b, the rare earth ions include one or more of trivalent europium ions, trivalent terbium ions, trivalent dysprosium ions, trivalent erbium ions and trivalent samarium ions.
Compared with the prior art, the invention has the beneficial effects that:
the core-shell structure prepared by the invention has the characteristics of adjustable light emission eutectic and dual light emission of long-life rare earth ions; the organic eutectic is compounded with the rare earth ions for the first time, and on the premise of keeping the light emission of the organic eutectic, the light emission of the rare earth ions is introduced into the system, so that the energy transfer of the organic eutectic system is realized.
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In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the embodiments will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and for those skilled in the art, other related drawings can be obtained according to the drawings without inventive efforts.
FIG. 1A is an SEM photograph of an organic co-crystal of terpyridine-1, 2-diiodotetrafluorobenzene (Tpy-1, 2-DITFB);
FIG. 1 SEM image of a core-shell structure of Tpy-1,2-DITFB @ @ Eu-Tpy;
FIG. 2A EDX spectrum of a Tpy-1,2-DITFB organic co-crystal;
FIG. 2B EDX spectrum of a Tpy-1,2-DITFB @ Eu-Tpy core-shell structure;
FIG. 3A is a fluorescent image of an organic co-crystal of Tpy-1,2-DITFB under UV irradiation;
FIG. 3B is a photograph of fluorescent imaging of a Tpy-1,2-DITFB @ Eu-Tpy core-shell structure under UV illumination;
FIG. 4A is a luminescence emission fluorescence spectrum of a Tpy-1,2-DITFB organic co-crystal;
FIG. 4B Dual light emission fluorescence spectra of a Tpy-1,2-DITFB @ Eu-Tpy core-shell structure;
FIG. 5A is an SEM photograph of 1O-phenanthroline-1, 2,4, 5-tetracyanobenzene (Phen-TCNB) organic cocrystals;
fig. 5a2 EDX spectrum of phenanthroline-1, 2,4, 5-tetracyanobenzene (Phen-TCNB) organic co-crystal;
FIG. 5B1 Phen-TCNB @ Eu-Phen core-shell structure SEM photograph;
FIG. 5B2 Phen-TCNB @ Eu-Phen core-shell structure EDX spectrum;
FIG. 5C1 SEM photograph of core-shell structure of Phen-TCNB @ Tb-Phen complex;
FIG. 5C2 EDX spectra of core-shell structure of Phen-TCNB @ Tb-Phen complex;
FIG. 6A1 Phen-TCNB organic eutectic fluorescence imaging;
FIG. 6A2 Phen-TCNB organic eutectic fluorescence spectra;
FIG. 6B1 fluorescence imaging of Phen-TCNB @ Eu-Phen core-shell structures;
FIG. 6B2 fluorescence spectra of Phen-TCNB @ Eu-Phen core-shell structure;
FIG. 6C1 fluorescence imaging of Phen-TCNB @ Tb-Phen core-shell structure;
FIG. 6C2 fluorescence spectra of Phen-TCNB @ Tb-Phen core-shell structure.
Detailed Description
The present invention will be further described with reference to specific embodiments, which are implemented on the premise of the technology of the present invention, and detailed embodiments are given, 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 an eutectic core and a rare earth complex shell; the eutectic kernel comprises eutectic main molecules which are coordinated with rare earth ions and eutectic acceptor molecules which are assembled with the eutectic main molecules through hydrogen bonds; the rare earth complex crystal shell is a rare earth complex formed in a surface lattice region of a eutectic by coordinating rare earth ions with host molecules in the surface lattice of the eutectic through an epitaxial coordination growth method.
Specifically, the co-crystal donor molecule comprises one or more of phenanthroline, bipyridine, 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.
A preparation method of an organic eutectic @ rare earth complex core-shell structure with double light emission characteristics comprises the following steps: dropping a solution with a certain concentration and containing one or more rare earth ions on the surface of the eutectic, performing heat treatment to ensure that the rare earth ions are coordinated with donor molecules in the surface crystal lattice of the eutectic, and growing a white rare earth complex on the surface of the organic eutectic to form a rare earth complex shell, thereby obtaining the core-shell structure of the organic eutectic @ rare earth complex. The method specifically comprises the following steps:
a. dissolving a co-crystal host molecule and a co-crystal guest molecule in acetonitrile solution according to the proportion of 1:1, and preparing a single organic co-crystal by a method of slowly volatilizing a solvent;
b. and 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 heat-treated eutectic surface, and coating a layer of white rare earth ion complex on the eutectic surface 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. Terpyridine (Tpy) is taken as a co-crystal host molecule, 1, 2-diiodotetrafluorobenzene (1,2-DITFB) is taken as a co-crystal guest molecule, the co-crystal host molecule and the co-crystal guest molecule are dissolved in acetonitrile solution according to the proportion of 1:1, and the Tpy-1,2-DITFB eutectic is obtained by a method of slowly volatilizing a solvent.
b. B, placing the single eutectic crystal obtained in the step a on a heating table at 50 ℃ for heat treatment for 1 minute, and placing 20 mu L of EuCl3And dripping ethanol solution on the surface of the eutectic crystal subjected to heat treatment, and coating a layer of white rare earth ion complex on the surface of the eutectic crystal to obtain the Tpy-1,2-DITFB @ Eu-Tpy core-shell structure.
The morphology of the eutectic and organic eutectic @ rare earth complex core-shell structure obtained in example 1 was observed with a scanning electron microscope SEM. As shown in fig. 1A, the Tpy-TFP eutectic was observed to be smooth on the surface, while the core-shell structure was smooth on the surface, as shown in fig. 1. The surface composition of the eutectic, organic eutectic and rare earth complex core-shell structure obtained in example 1 was characterized by X-ray energy spectroscopy (EDX). Fig. 2A shows that C and N elements can be identified in the EDX spectrum of the eutectic, and C, N and Eu elements can be identified in the EDX spectrum of the core-shell structure3+The elements are shown in fig. 2B.
Example 2
The core-shell structure obtained in example 1 was subjected to fluorescence spectroscopy.
And (3) observing fluorescence imaging of the eutectic and organic eutectic @ rare earth complex core-shell structure obtained in the example 1 by using a fluorescence microscope. And irradiating the single eutectic and the core-shell structure by using ultraviolet light with the wavelength of 365nm, and synchronously collecting fluorescence imaging and fluorescence spectrum. As shown in FIG. 3A, it can be observed that the Tpy-TFP eutectic shows green fluorescence, and the fluorescence band of the organic eutectic is 500-700 nm, as shown in FIG. 4A. The core-shell structure of Tpy-1,2-DITFB @ Eu-Tpy shows red fluorescence, as shown in FIG. 3B, the fluorescence characteristic peaks of trivalent europium ions at 595, 612, 623 and 702nm are respectively assigned to5D0→7F1、5D0→7F2、5D0→7F3And5D0→7F4as shown in fig. 4B.
Example 3
A preparation method of an organic eutectic @ rare earth complex core-shell structure with double light emission characteristics comprises the following steps:
a. dissolving phenanthroline (Phen) serving as a co-crystal host molecule and 1,2,4, 5-Tetracyanobenzene (TCNB) serving as a co-crystal guest molecule in acetonitrile solution according to a ratio of 1:1, and slowly volatilizing a solvent to obtain the Phen-TCNB eutectic.
B, placing the single eutectic crystal obtained in the step a on a heating table at 50 ℃ for heat treatment for 1 minute, and respectively placing 10 mu L of EuCl3Ethanol solution and 10. mu.L of TbCl3And (3) dripping ethanol solution on the surface of the heat-treated eutectic crystal, and coating a layer of white rare earth ion complex on the surface of the eutectic crystal to respectively obtain a Phen-TCNB @ Eu-Phen and Phen-TCNB @ Tb-Phen core-shell structure.
The morphology of the eutectic, organic eutectic and rare earth complex core-shell structure obtained in example 3 was observed with a scanning electron microscope SEM. As shown in fig. 5a1, the Tpy-TFP eutectic was observed to be flat on the surface. The surface of the core-shell structure is smooth, as shown in FIG. 5B1 and FIG. 5C 1. The eutectic and the surface components of the organic eutectic @ rare earth complex core-shell structure obtained in example 3 were characterized by X-ray energy spectroscopy (EDX). C and N elements can be identified in an 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. 5A23+Elements, as shown in fig. 5B 2. C, N and Tb can be identified in EDX spectrum of Phen-TCNB @ Tb-Phen core-shell structure3+Elements, as shown in fig. 5C 2.
Example 4
The core-shell structure obtained in example 3 was subjected to fluorescence spectroscopy.
And (3) observing fluorescence imaging of the eutectic and organic eutectic @ rare earth complex core-shell structure obtained in the example 3 by using a fluorescence microscope. And irradiating the single eutectic and the core-shell structure by using ultraviolet light with the wavelength of 365nm, and synchronously collecting fluorescence imaging and fluorescence spectrum of the single eutectic and the core-shell structure. As shown in FIG. 6A1, it can be observed that the Phen-TCNB eutectic crystal shows blue fluorescence, and a wide fluorescence spectrum of the organic eutectic crystal exists between 400 nm and 600nmA belt, as shown in fig. 6a 2. The core-shell structure of Phen-TCNB @ Eu-Phen shows red fluorescence, as shown in figure 6B1, fluorescence characteristic peaks of trivalent europium ions at 595 nm, 612 nm and 702nm, as shown in figure 6B2, belonging to trivalent europium ions5D0→7F1、5D0→7F2And5D0→7F4and (4) transition. The core-shell structure of Phen-TCNB @ Tb-Phen shows green fluorescence, and as shown in FIG. 6C1, the fluorescence characteristic peaks of trivalent terbium ions are at 491, 544, 584 and 621nm, and the fluorescence characteristic peaks belong to the terbium ions respectively5D4→7F6、5D4→7F5、5D4→7F3And5D4→7F3the electron transition is shown in fig. 6C 2.
It is to be noted that the foregoing is only illustrative of the preferred embodiments of the present invention and the technical principles employed. 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, although the present invention has been described in greater detail by the above embodiments, the present invention is not limited to the above embodiments, and may include other equivalent embodiments without departing from the spirit of the present invention, and the scope of the present invention is determined by the scope of the appended claims.

Claims (7)

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 kernel comprises eutectic main body molecules which are coordinated with rare earth ions and eutectic acceptor molecules which are assembled with the eutectic main body molecules through hydrogen bonds;
the rare earth complex shell is a rare earth complex formed in the surface area of the eutectic crystal by coordinating trivalent rare earth ions with host molecules in the surface lattice of the organic eutectic crystal through an epitaxial coordination growth method.
2. The organic eutectic @ rare earth complex core-shell structure with dual light emission characteristics as claimed in claim 1, wherein: the co-crystal donor molecule comprises one or more of phenanthroline, bipyridine, terpyridine and derivatives thereof.
3. The organic eutectic @ rare earth complex core-shell structure with dual light emission characteristics as claimed in claim 1, wherein: 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.
4. The organic eutectic @ rare earth complex core-shell structure with dual light emission characteristics as claimed in 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.
5. A preparation method of an organic eutectic @ rare earth complex core-shell structure with double light emission characteristics is characterized by comprising the following steps:
dropping a solution with a certain concentration and containing one or more rare earth ions on the surface of the eutectic, performing heat treatment to ensure that the rare earth ions are coordinated with donor molecules in the surface crystal lattice of the eutectic, and growing a white rare earth complex on the surface of the organic eutectic to form a rare earth complex crystal shell, thereby obtaining the core-shell structure of the organic eutectic @ rare earth complex.
The preparation method of the organic eutectic @ rare earth complex core-shell structure with the double light emission characteristics specifically comprises the following steps:
a. dissolving host molecules of the eutectic and molecules of the eutectic guest in acetonitrile solution according to the ratio of 1:1, and preparing the single organic eutectic by a method of slowly volatilizing the solvent.
b. And 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 eutectic subjected to heat treatment, 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.
6. The preparation method of the organic eutectic @ rare earth complex core-shell structure with the dual light emission characteristic according to claim 1, is characterized in that: and b, heating the heating table at 50 ℃ for 1 minute.
7. The preparation method of the organic eutectic @ rare earth complex core-shell structure with the dual light emission characteristic according to claim 1, is characterized in that: 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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