CN113105883B - Supermolecule afterglow luminescent compound based on diphenyl acetylene and cyclodextrin, preparation and application - Google Patents

Supermolecule afterglow luminescent compound based on diphenyl acetylene and cyclodextrin, preparation and application Download PDF

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CN113105883B
CN113105883B CN202110283837.1A CN202110283837A CN113105883B CN 113105883 B CN113105883 B CN 113105883B CN 202110283837 A CN202110283837 A CN 202110283837A CN 113105883 B CN113105883 B CN 113105883B
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cyclodextrin
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diphenyl acetylene
afterglow
diphenylacetylene
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CN113105883A (en
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李明德
黄冠衡
庞君洪
邓梓祺
党丽
李海林
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Shantou University
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Abstract

The invention relates to a supermolecule afterglow luminous compound based on diphenyl acetylene and cyclodextrin, which is constructed by a supermolecule self-assembly method of diphenyl acetylene, diphenyl acetylene derivatives and alpha-cyclodextrin; the diphenyl acetylene or the diphenyl acetylene derivative enters the alpha-cyclodextrin to form a supermolecule host-guest complex. The supermolecule compound is prepared by self-assembly through a simple and convenient solvent volatilization or solid state grinding process, has two long-life luminous processes, changes the color of afterglow from green to blue-violet along with the change of the supermolecule compound over time, and can be applied to the fields of anti-counterfeiting and coding. The supermolecule compound of the invention can also utilize water, ethanol and other economic and environment-friendly organic solvents, can realize the control of afterglow luminescence by a circulation switch, and has the potential of being applied to the fields of erasable materials, information storage and the like.

Description

Supermolecule afterglow luminescent compound based on diphenyl acetylene and cyclodextrin, preparation and application
Technical Field
The invention relates to the field of novel long afterglow luminescent materials, in particular to a supermolecule afterglow luminescent compound based on diphenyl acetylene and cyclodextrin, and preparation and application thereof.
Background
The pure organic long afterglow luminescent material has large stokes shift, long luminescent life and relatively low price due to the singlet state, so that the pure organic long afterglow luminescent material is widely applied to the fields of data encryption, biological imaging, information storage, organic Light Emitting Diodes (OLED) and the like (adv. Mater.,2016, 28, 9920-9940.). The realization of long persistence materials is a challenging problem because long persistence materials involve triplet emission, which is susceptible to non-radiative transitions or deactivation by oxygen at ambient conditions.
The current methods for constructing pure organic long afterglow luminescent materials are relatively large, such as the introduction of specific phosphorescent groups (e.g. carbazole) by organic synthesis (nat. Commun.,2020,11,842), high molecular polymerization (nat. Commun.,2019 10, 4247.), formation of H-aggregates (nat. Mater.,2015,14,685-690.), crystal engineering (Angew. Chem. Int. Ed.2020,59, 10032-10036.), formation of hydrogen bonds, and interaction by host and guest (Angew. Chem. Int. Ed.2020,59, 9293-9298). However, the synthesis process by the organic synthesis or the polymerization method is complicated, and is easy to cause pollution and high in cost. The method for constructing the afterglow material by a crystal engineering mode is simple, but the screening of a proper system is time-consuming and has undefined targeting. And the luminescence color of the afterglow of most existing afterglow materials is single and cannot be changed with time.
Disclosure of Invention
The invention aims to provide a multifunctional supermolecule compound with double long afterglow emission, which is constructed by a supermolecule self-assembly method by using diphenyl acetylene and cyclodextrin. The material can emit green light under the condition of ultraviolet excitation (240-365 nm), and can still emit afterglow luminescence for about 2 seconds after the ultraviolet lamp light source is removed. The afterglow luminescence consists of two parts of long afterglow Room Temperature Phosphorescence (RTP) and long afterglow heat-activated delayed fluorescence (TADF). In addition, the material of the invention has low cost, and the synthesis condition is simple and environment-friendly.
A supermolecule afterglow luminous compound based on diphenyl acetylene and cyclodextrin is prepared from diphenyl acetylene or diphenyl acetylene derivative and alpha-cyclodextrin through supermolecule self-assembling.
Preferably, the diphenylacetylene derivative comprises 4- (4-fluorophenylacetylene)Phenyl) phenol (OF-F-DPA), 4' -difluorodiphenylacetylene (2F-DPA), 4-amino-diphenylacetylene (NH) 2 -DPA) or 4-aldehyde-diphenylacetylene (CHO-DPA), 4- (4-fluorophenylethynyl) phenol (OH-F-DPA).
Preferably, the molar ratio of the tolane or the tolane derivative to the alpha-cyclodextrin is 1:1-2, wherein the diphenyl acetylene or the diphenyl acetylene derivative enters the alpha-cyclodextrin to form a supermolecule host-guest complex. If the diphenylacetylene and alpha-cyclodextrin are greater than 1:1, a part of the diphenyl acetylene cannot enter the cavity, and the light emission of the diphenyl acetylene can be observed. Ratio 1:1-2, and 1:1 is not different.
The preparation method of the supramolecular afterglow luminescent compound based on diphenylacetylene and cyclodextrin comprises the following steps: molar ratio 1:1, dissolving the diphenyl acetylene or the diphenyl acetylene derivative and alpha-cyclodextrin in a mixed solution of water and ethanol or capronitrile for self-assembly, and obtaining the supermolecular compound crystal after the solvent is completely volatilized.
The preparation method of the supramolecular afterglow luminescent compound based on diphenylacetylene and cyclodextrin comprises the following steps: molar ratio 1:1 or a diphenylacetylene derivative and alpha-cyclodextrin in a mortar, adding a small amount of water, and grinding to obtain a supramolecular complex powder.
The application of the supramolecular afterglow luminescent compound based on diphenylacetylene and cyclodextrin is used for anti-counterfeiting and encoding.
The application of the supramolecular afterglow luminescent compound based on diphenylacetylene and cyclodextrin is used for erasable materials and information storage.
The invention assembles the diphenyl acetylene into the cyclodextrin, the size of the diphenyl acetylene isThe inner cavity of the alpha-cyclodextrin is +.>Exactly one diphenylacetylene molecule can enter alfa-cyclodextrinA cavity. After entering, long afterglow luminescence can be observed, and only one diphenylacetylene molecule in the inner cavity is verified by single crystal structure analysis. After entering the sample, the long afterglow luminescence can be observed only by illuminating the supermolecule compound, and the sample is very stable. No significant photodecomposition occurs. And the diphenyl acetylene can enter and exit the cyclodextrin cavity through spraying water and organic solvent, thereby realizing the long afterglow luminescence on and off. Therefore, the supermolecule afterglow luminescent compound of the diphenyl acetylene and the cyclodextrin is a long afterglow luminescent material which is very environment-friendly, simple to operate and low in cost and has a luminescent switch function.
Compared with the prior art, the invention constructs the supermolecule host-guest composite material of the diphenyl acetylene and the derivative thereof and the alpha-cyclodextrin by a supermolecule self-assembly method; has the following advantages:
(1) The supermolecule compound has the functions of dual long afterglow emission and the like, so that the supermolecule compound has time-dependent afterglow luminescence, namely, the color of the afterglow changes from green to blue-violet along with the change of time, and the supermolecule compound can be applied to the fields of anti-counterfeiting and coding;
(2) Space charge transfer exists between main objects and main objects of the supermolecule compound, and long-distance charge transfer and slow charge recombination lead to afterglow; not only can emit long afterglow phosphorescence under the condition of room temperature, but also has the characteristic of long afterglow heat activation delayed fluorescence;
(3) The supermolecule compound of the invention can use water as the driving force of self-assembly, can be used as a switch, and can be used for de-designing an activated type afterglow material so as to improve the anti-counterfeiting grade. The method can utilize water, ethanol and other economic and environment-friendly organic solvents, can realize the control of afterglow luminescence by a circulation switch, and has the potential of being applied to the fields of erasable materials, information storage and the like.
(4) The supermolecule compound can be prepared by self-assembly through a simple and convenient solvent volatilization or solid grinding process by using low-cost small molecules, and is simple, convenient and environment-friendly.
Drawings
FIG. 1 is a schematic representation of the composition of the supramolecular complexes of the present invention, as well as the preparation using solvent evaporation and solid phase milling processes;
FIG. 2 shows (1) a single crystal structure of a supramolecular afterglow luminescent complex of diphenylacetylene and cyclodextrin, (2) an ultraviolet-visible absorption spectrum of three supramolecular complexes of the present invention, (3) an emission spectrum of a supramolecular complex of the present invention, and (4) a kinetic decay curve of three supramolecular complexes of the present invention under normal temperature air;
FIG. 3 is a photograph of three objects and supermolecule complexes formed by them under sunlight and ultraviolet light, (2) the temperature change emission spectrum of 2F-DPA-CD complex, (3) the kinetic decay curve of OH-F-DPA-CD at 486nm under different temperature conditions, and (4) the kinetic decay curve of OH-F-DPA-CD at 369nm under different temperature conditions;
FIG. 4 is a plot of the femtosecond transient absorption spectra of a 2F-DPA-CD complex at 290nm excitation and the kinetic decay comparisons at 240nm,254nm and 290nm excitation;
FIG. 5 (a) shows the front-line orbitals of OH-F-DPA-CD, (b) shows the energy level diagrams of three guests and cyclodextrin, (c) shows the single crystal structure of 2F-DPA-CD, and (d) shows the ultra-long-life luminescence mechanism;
in fig. 6, (1) is a process of changing the color of afterglow with time, (2) is a schematic diagram of an encoding method developed based on water as an activator, and (3) is a cyclic switching process of realizing afterglow by water and an organic solvent.
Detailed Description
The present invention will be described in further detail with reference to the accompanying drawings, for the purpose of making the objects, technical solutions and advantages of the present invention more apparent.
Example 1
Preparation of supermolecule afterglow luminous compound based on diphenyl acetylene and cyclodextrin by solid phase method
As shown in FIG. 1, diphenylacetylene (DPA) or a diphenylacetylene derivative 4- (4-fluorophenylethynyl) phenol (OF-F-DPA), 4' -difluorodiphenylacetylene (2F-DPA), 4-amino-diphenylacetylene (NH) 2 Mixing sample powder of (E) -DPA) or 4-aldehyde-diphenyl acetylene (CHO-DPA) and alpha-cyclodextrin in a molar ratio of 1:1 in a mortar, adding a small amount of water, and grindingThe supermolecular composite powder with long afterglow luminescence property can be obtained.
Example 2
Preparation of supermolecule afterglow luminous compound based on diphenyl acetylene and cyclodextrin by solvent volatilizing method
As shown in FIG. 1, diphenylacetylene (DPA) or a diphenylacetylene derivative 4- (4-fluorophenylethynyl) phenol (OF-F-DPA), 4' -difluorodiphenylacetylene (2F-DPA), 4-amino-diphenylacetylene (NH) 2 -DPA) or 4-aldehyde-diphenyl acetylene (CHO-DPA) or 4- (4-fluorophenyl ethynyl) phenol (OH-F-DPA) and alpha-cyclodextrin are dissolved in a mixed solution of water and ethanol or capronitrile according to a molar ratio of 1:1 to completely dissolve sample powder, and after the solvent is completely volatilized at room temperature, the supermolecule compound crystal with long afterglow luminescence property can be obtained.
Performance testing
The supramolecular complexes DPA-CD, 2F-DPA-CD, OH-F-DPA-CD obtained in example 1 and example 2 were subjected to performance tests.
As shown in (1) of FIG. 2, from the single crystal structures of three supramolecular complexes DPA-CD, 2F-DPA-CD, OH-F-DPA-CD, the guest molecule diphenylacetylene enters the interior of the host molecule cyclodextrin to constitute the supramolecular host-guest complex. The size of the alpha-cyclodextrin cavity isWith guest molecule diphenylacetylene->The driving force for the entrance of the tolane into the cyclodextrin to form supramolecular complexes is due to hydrophobic interactions. The diphenyl acetylene is hydrophobic, the outer part of the cyclodextrin is hydrophilic, the cavity is hydrophobic, and after a small amount of water is added, the water drives the diphenyl acetylene to enter the cyclodextrin.
As shown in FIG. 2 (2), the absorption of the three supramolecular complexes of the present invention is in the ultraviolet region, while there is a bimodal emission of the three supramolecular complexes, one peak at 360nm and one peak at 460nm, as shown in FIG. 2 (3). The lifetime of the bimodal emission of the three supramolecular complexes at room temperature air was measured in milliseconds by photoluminescence lifetime tests as in fig. 2 (4).
As shown in fig. 3 (1), the color of luminescence changes after the formation of the supramolecular complex as compared with the guest itself. After the ultraviolet lamp is removed, the afterglow luminescence of about 2 seconds can still be seen, which indicates that the supermolecule compound has the property of long afterglow luminescence at room temperature. As shown in (2) of fig. 3, the intensities of the two light emission peaks at 370nm and 480nm show different changes as the temperature rises. The luminescence of the two peaks is proved to be from different luminescence centers by the test of temperature change dynamics decay, and the luminescence at 460nm is from room temperature phosphorescence emission, because the luminescence life of the luminescence is monotonically decreasing along with the temperature rise as shown in (3) of fig. 3, and the lives of the three are DPA-CD:354ms, OH-F-DPA-CD:292ms and 2F-DPA-CD:245ms respectively. Whereas long-life luminescence at 360nm has temperature dependence, and the lifetime rises and falls with temperature, so the luminescence type is Thermally Activated Delayed Fluorescence (TADF) as shown in fig. 3 (4), and the lifetimes of the three are DPA-CD:134ms, OH-F-DPA-CD:282ms,2F-DPA-CD:256ms.
As shown in fig. 4, through the test of the femtosecond transient absorption spectrum, the formation of a supermolecule charge transfer state is observed, meanwhile, the front orbit of the supermolecule complex is calculated, the calculated result is found to be identical with the experimental result, and the intermolecular space charge transfer exists between the host and the guest. Further, the transport distance of charges in the supramolecular complex was measured using femtosecond transient absorption spectroscopy, in the DPA-CD complex, the charges were able to conduct 2.32mm.
As shown in fig. 5 (a) and 5 (b), the front-line orbital distribution and the energy level between the host and guest satisfy the condition for charge transfer to occur. In fig. 5, (c) is a single crystal structure of the supramolecular complex, and this unique spatial structure enables charge transfer in the diphenylacetylene chain, resulting in the generation of a long-life charge transfer state, and thus the luminescence process has an ultra-long life. The mechanism of the ultra-long lifetime luminescence is shown in fig. 5 (d), and long-distance charge transport results in the formation of long-lived charge transfer states, which bring the lifetimes of TADF and RTP to the order of hundred milliseconds.
Since the supermolecular composite of the present invention has both room temperature phosphorescence of long afterglow and thermally activated delayed fluorescence, its afterglow color changes over time from green to blue as shown in fig. 6 (1), which can improve the disadvantage that most of the afterglow materials today have only a single afterglow color, while improving the ability of information storage and encoding. By using water as an activator to graphically or digitally encode the mixture of pre-activated complex and host-guest as shown in fig. 6 (2), two sets of information can be obtained after removal of the uv lamp excitation before and after activation, and this strategy of activation can improve the security of the information encoding. As shown in fig. 6 (3), since water can drive self-assembly to form a complex and an organic solvent can be self-assembled, a switch which can realize afterglow by using water and an organic solvent in a circulating manner is expected to be used for a material which can be repeatedly erased and written.
Comparative example 1
Self-assembling with beta-cyclodextrin with larger cavity aperture and diphenyl acetylene.
Comparative example 2
And (3) self-assembling the gamma-cyclodextrin with larger cavity aperture and the diphenyl acetylene.
Comparative example 3
And (3) self-assembling the nitro-substituted diphenyl acetylene and the alpha-cyclodextrin.
Comparative example 4
The stilbene is self-assembled with the alpha-cyclodextrin.
None of comparative examples 1 to 4 obtained a supramolecular afterglow luminescent complex.

Claims (5)

1. A supramolecular afterglow luminescent compound based on diphenylacetylene and cyclodextrin, which is characterized in that the molar ratio of the diphenylacetylene or the diphenylacetylene derivative to the alpha-cyclodextrin is 1:1-2, enabling the diphenyl acetylene or the diphenyl acetylene derivative to enter the alpha-cyclodextrin to form a supermolecule host guest afterglow luminescent compound; the diphenyl acetylene derivative is 4- (4-fluorophenyl ethynyl) phenol or 4,4' -difluoro diphenyl acetylene.
2. The method for preparing the supramolecular afterglow luminescent compound based on diphenylacetylene and cyclodextrin according to claim 1, comprising the following steps: molar ratio 1:1, dissolving the diphenyl acetylene or the diphenyl acetylene derivative and alpha-cyclodextrin in a mixed solution of water and ethanol or capronitrile for self-assembly, and obtaining the supermolecule afterglow luminescent compound crystal after the solvent is completely volatilized.
3. The method for preparing the supramolecular afterglow luminescent compound based on diphenylacetylene and cyclodextrin according to claim 1, comprising the following steps: molar ratio 1:1 or the powder of the diphenyl acetylene or the diphenyl acetylene derivative and the alpha-cyclodextrin are mixed in a mortar, and the mixture is ground after water is added, so that the supermolecule afterglow luminous compound powder is obtained.
4. The use of supramolecular afterglow luminescent complexes based on diphenylacetylene and cyclodextrins according to claim 1, characterized by their use for anti-counterfeiting and coding.
5. Use of supramolecular afterglow luminescent complexes based on diphenylacetylene and cyclodextrin according to claim 1, for erasable materials and information storage.
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