CN112940039B - Eutectic compound with solid fluorescence performance and preparation method and application thereof - Google Patents
Eutectic compound with solid fluorescence performance and preparation method and application thereof Download PDFInfo
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- CN112940039B CN112940039B CN202110166598.1A CN202110166598A CN112940039B CN 112940039 B CN112940039 B CN 112940039B CN 202110166598 A CN202110166598 A CN 202110166598A CN 112940039 B CN112940039 B CN 112940039B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- 230000005496 eutectics Effects 0.000 title claims abstract description 49
- 239000007787 solid Substances 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- VYXSBFYARXAAKO-WTKGSRSZSA-N chembl402140 Chemical compound Cl.C1=2C=C(C)C(NCC)=CC=2OC2=C\C(=N/CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-WTKGSRSZSA-N 0.000 claims abstract description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- 239000000243 solution Substances 0.000 claims description 12
- 239000002243 precursor Substances 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 238000001291 vacuum drying Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 5
- 125000000129 anionic group Chemical group 0.000 abstract description 8
- 239000007850 fluorescent dye Substances 0.000 abstract description 6
- 238000004020 luminiscence type Methods 0.000 abstract description 5
- 125000002091 cationic group Chemical group 0.000 abstract description 3
- 239000002131 composite material Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 239000000843 powder Substances 0.000 description 10
- 238000004220 aggregation Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000000985 reflectance spectrum Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- VYXSBFYARXAAKO-UHFFFAOYSA-N ethyl 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoate;hydron;chloride Chemical compound [Cl-].C1=2C=C(C)C(NCC)=CC=2OC2=CC(=[NH+]CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000005220 pharmaceutical analysis Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Luminescent Compositions (AREA)
Abstract
The invention belongs to the field of composite materials, and discloses a eutectic compound with solid fluorescence performance, a preparation method and application thereof, which are creatively prepared by using anionic { alpha-Mo 8 O 26 The molecular cluster and cationic organic fluorescent dye molecular rhodamine 6G are dissolved and recrystallized to obtain { [ C ] 28 H 31 ClN 2 O 3 ] 2 [N(C 4 H 9 ) 4 ] 2 }[α‑Mo 8 O 26 ]The fluorescence intensity of the eutectic compound is enhanced by nearly 14 times compared with that of the solid rhodamine 6G. The composite material disclosed by the invention not only enriches the application of polyoxometallate in solid state luminescence, but also provides a precious experience for researchers to further research solid state luminescent materials and research hot spot aggregate luminescence and luminescence mechanism in recent years.
Description
Technical Field
The invention belongs to the field of composite materials, and particularly relates to a eutectic compound with solid state fluorescence performance, and a preparation method and application thereof.
Background
Fluorescence is a property of substances that plays a vital role for many technologies, such as OLED, biomarkers, etc. Fluorescence is also observed in many classes of dye molecules, which are capable of emitting very strong fluorescence in dilute solutions, whereas at high concentrations their fluorescence intensity is reduced or hardly reduced, which is the so-called aggregation-induced quenching. Exciton coupling occurs when dyes are closely packed in the solid state, creating new exciton states, and quenching occurs.
Therefore, how to maintain the strong luminescence properties of organic fluorescent dye molecules in the solid state is a problem that scientists are urgent to solve.
Disclosure of Invention
In view of the above, an object of the present invention is to provide a eutectic compound that maintains strong luminescence properties of organic fluorescent dye molecules in a solid state, in view of the problems existing in the prior art.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
eutectic compound with solid state fluorescence properties having a chemical molecular formula { [ C ] 28 H 31 ClN 2 O 3 ] 2 [N(C 4 H 9 ) 4 ] 2 }[α-Mo 8 O 26 ]The molecular structure is shown as formula 1:
further, the anionic group of the eutectic compound is [ alpha-Mo 8 O 26 ] 4- And the structure of the anionic group is shown as formula 2:
it is worth noting that the structure in the eutectic compound of the present invention is determined by single crystal X-ray diffraction: { [ C ] 28 H 31 ClN 2 O 3 ] 2 [N(C 4 H 9 ) 4 ] 2 }[α-Mo 8 O 26 ]Wherein the anionic moiety [ alpha-Mo 8 O 26 ] 4- Is made up of 6 { MoO } 6 An octahedron is formed into a ring structure by a mode of sharing edges, and the upper end and the lower end of the ring are respectively provided with a { MoO }, the two ends of the ring are respectively provided with a ring structure 4 Tetrahedra, in addition, 8 Mo atoms are also connected by 6 di-and 6 tri-bridging oxygens.
A second object of the present invention is to provide a method for producing the eutectic compound.
In order to achieve the above object, the present invention provides the following technical solutions:
the preparation method of the eutectic compound with the solid state fluorescence performance comprises the following steps:
I. synthesis of [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]Precursor: moO is carried out 3 And [ (n-C) 4 H 9 ) 4 N]Room temperature of OH aqueous solutionStirring to obtain white milk-like substance, filtering, vacuum drying, dissolving in acetonitrile, and crystallizing in refrigerator;
II. The [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]Dissolving in acetonitrile, adding rhodamine 6G dissolved in an organic solvent to obtain a yellow solution, and volatilizing the solvent to obtain the eutectic compound with solid fluorescence.
Further, in the step I, moO 3 And [ (n-C) 4 H 9 ) 4 N]The molar ratio of OH was 2:1.
Further, the stirring time in the step I is 60 hours, and the vacuum drying time is 10-20 hours.
Further, in the step II, [ N (C 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]And the molar ratio of R6G is (2:1-8:1).
Further, the organic solvent in step II includes acetonitrile, methanol, N' -dimethylformamide or dichloromethane.
It is worth to say that the synthesis method of the invention is simple and efficient, and only N (C 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]The precursor is mixed with rhodamine 6G, and the crystal which emits red fluorescence can be obtained after the solvent is volatilized. Among them, rhodamine 6G is one of rhodamine family dyes with high fluorescence property, can be used as laser dye, has very high light stability, high fluorescence quantum yield and low cost, and is often used as a reference for measuring fluorescence quantum yield of other substances, but rhodamine 6G can be aggregated in a solid state due to pi-pi interaction, so that the high fluorescence intensity in a dilute solution can not be maintained in the solid state. The polyoxometallate is an anionic type of metalloxy cluster, and the cationic rhodamine 6G and the anionic polyoxometallate are compounded, so that aggregation among rhodamine 6G molecules can be reduced, the rhodamine 6G molecules are separated, and the fluorescence intensity in a solid state is enhanced.
A third object of the present invention is to provide the use of the eutectic compound.
In order to achieve the above object, the present invention provides the following technical solutions:
the eutectic compound with solid fluorescence performance is applied to preparing temperature sensors, pressure sensors, concentration sensors, gas sensors, electrochemical sensors, electroluminescent devices, pharmaceutical analysis, environmental monitoring, biological sensing, biological marking, biological imaging or analysis detection materials and devices.
Compared with the prior art, the invention has the following advantages and beneficial effects:
1. according to the invention, cationic rhodamine 6G and anionic polyoxometallate are compounded, so that aggregation among rhodamine 6G molecules can be reduced, and the rhodamine 6G molecules are separated, so that the fluorescence intensity in a solid state is enhanced;
2. the strategy of separating the aggregation state of fluorescent dye molecules by using the polyoxometallate with adjustable structure and charge provides more possibility and basis for preparing eutectic compounds with strong fluorescence in more solid states;
3. the synthesis method is simple and convenient, mild in synthesis condition and high in yield, and has potential of industrial application.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for the description of the embodiments or the prior art will be briefly described below, it will be apparent that the drawings in the following description are only embodiments of the present invention, and other drawings can be obtained from the provided drawings without inventive effort for a person skilled in the art
FIG. 1 is a molecular structure diagram of a eutectic compound of the present invention.
FIG. 2 is a molecular structure diagram of anions of the present invention.
FIG. 3 is a photograph of a crystal of a eutectic compound of the present invention.
FIG. 4 is a graph showing the diffuse reflectance spectrum of the eutectic compound and rhodamine 6G of the present invention.
FIG. 5 is a graph showing fluorescence emission of the eutectic compound of the present invention and rhodamine 6G under irradiation of an ultraviolet lamp at 365 nm.
FIG. 6 is a solid fluorescence spectrum of the eutectic compound and rhodamine 6G of the present invention.
FIG. 7 is a graph of fluorescence lifetime of rhodamine 6G of the present invention.
FIG. 8 is a graph of fluorescence lifetime of a eutectic compound of the present invention.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The present invention will be further specifically illustrated by the following examples, which are not to be construed as limiting the invention, but rather as falling within the scope of the present invention, for some non-essential modifications and adaptations of the invention that are apparent to those skilled in the art based on the foregoing disclosure.
Example 1
A eutectic compound with solid state fluorescence performance and a preparation method thereof comprise the following specific steps:
I. synthesis of [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]Precursor: moO is carried out 3 Is dissolved in [ (n-C) 4 H 9 ) 4 N]OH aqueous solution, wherein MoO 3 And [ (n-C) 4 H 9 ) 4 N]The molar ratio of OH is 2:1, stirring vigorously for 60h, changing the pH of the mixture from 7.8 to 6.1, changing the gray suspension into white precipitate, filtering, vacuum drying for 10h to obtain white powder, wherein the white powder is [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]. Then the white powder is dissolved in acetonitrile, filtered, and the filtrate is put into a refrigerator for storage for standby.
II. 0.9mL of [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]Adding the precursor (0.1G/10 mL) into 2mL of rhodamine 6G (0.01G/10 mL) dissolved in acetonitrile to obtain a yellow solution, volatilizing the solvent to obtain the eutectic compound { [ C ] with solid state fluorescence performance 28 H 31 ClN 2 O 3 ] 2 [N(C 4 H 9 ) 4 ] 2 }[α-Mo 8 O 26 ]。
Example 2
A eutectic compound with solid state fluorescence performance and a preparation method thereof comprise the following specific steps:
I. synthesis of [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]Precursor: moO is carried out 3 Is dissolved in [ (n-C) 4 H 9 ) 4 N]OH aqueous solution, wherein MoO 3 And [ (n-C) 4 H 9 ) 4 N]The molar ratio of OH is 2:1, stirring vigorously for 60h, changing the pH of the mixture from 7.8 to 6.1, changing the gray suspension into white precipitate, filtering, vacuum drying for 20h to obtain white powder, wherein the white powder is [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]. Then the white powder is dissolved in acetonitrile, filtered, and the filtrate is put into a refrigerator for storage for standby.
II. 0.3mL of [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]The precursor (0.1G/10 mL) was added to 2mL of rhodamine 6G (4X 10) in acetonitrile -4 g/mL) to obtain yellow solution, and volatilizing the solvent to obtain the eutectic compound { [ C ] with solid state fluorescence performance 28 H 31 ClN 2 O 3 ] 2 [N(C 4 H 9 ) 4 ] 2 }[α-Mo 8 O 26 ]。
Example 3
A eutectic compound with solid state fluorescence performance and a preparation method thereof comprise the following specific steps:
I. synthesis of [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]Precursor:
MoO is carried out 3 Is dissolved in [ (n-C) 4 H 9 ) 4 N]OH aqueous solution, wherein MoO 3 And [ (n-C) 4 H 9 ) 4 N]The molar ratio of OH is 2:1, stirring vigorously for 60h, changing the pH of the mixture from 7.8 to 6.1, changing the gray suspension into white precipitate, filtering, vacuum drying for 13h to obtain white powder, namely [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]. Then the white powder is dissolved in acetonitrile, filtered, and the filtrate is put into a refrigerator for storage for standby.
II. 0.5mL of [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]The precursor (0.1G/10 mL) was added to 2mL of rhodamine 6G (3.65X10) -4 g/mL) to obtain yellow solution, and volatilizing the solvent to obtain the eutectic compound { [ C ] with solid state fluorescence performance 28 H 31 ClN 2 O 3 ] 2 [N(C 4 H 9 ) 4 ] 2 }[α-Mo 8 O 26 ]。
Example 4
A eutectic compound with solid state fluorescence performance and a preparation method thereof comprise the following specific steps:
I. synthesis of [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]Precursor:
MoO is carried out 3 Is dissolved in [ (n-C) 4 H 9 ) 4 N]OH aqueous solution, wherein MoO 3 And [ (n-C) 4 H 9 ) 4 N]The molar ratio of OH is 2:1, stirring vigorously for 60h, changing the pH of the mixture from 7.8 to 6.1, changing the gray suspension into white precipitate, filtering, vacuum drying for 16h to obtain white powder, namely [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]. Then the white powder is dissolved in acetonitrile, filtered, and the filtrate is put into a refrigerator for storage for standby.
II. 0.3mL of [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]The precursor (0.1G/10 mL) was added to 2mL of rhodamine 6G (3.65X10) -4 g/mL) to obtain yellow solution, and volatilizing the solvent to obtain the eutectic compound { [ C ] with solid state fluorescence performance 28 H 31 ClN 2 O 3 ] 2 [N(C 4 H 9 ) 4 ] 2 }[α-Mo 8 O 26 ]。
In order to further demonstrate the beneficial effects of the present invention for a better understanding thereof, the following assay experiments further illustrate the invention based on [ alpha ] -Mo 8 O 26 ]The strong solid state fluorescence enhancement of molecular clusters and organic fluorescent dye molecules and their synthesis, but not to be construed as limiting the invention, and the nature of the products obtained by other assay experiments performed by those skilled in the art based on the above summary and the use according to the above nature are also considered to be within the scope of the invention.
Experimental example 1 structural characterization of eutectic compounds with solid state fluorescence properties:
the eutectic compound of the present invention was confirmed by single crystal X-ray diffraction, and the anionic moiety [ alpha-Mo ] can be seen from FIGS. 1 and 2 8 O 26 ] 4- Is made up of 6 { MoO } 6 An octahedron is formed into a ring structure by a mode of sharing edges, and the upper end and the lower end of the ring are respectively provided with a { MoO }, the two ends of the ring are respectively provided with a ring structure 4 Tetrahedra, in addition, 8 Mo atoms are connected by 6 two-bridged oxygens and 6 three-bridged oxygens. Each { alpha-Mo 8 O 26 The molecular cluster and two rhodamine 6G molecules and two tetrabutyl groups are linked by electrostatic interactions or hydrogen bonds.
From fig. 3, it can be seen that the eutectic compound obtained by the preparation method disclosed in the present invention is reddish brown rod-like crystals.
Experimental example 2 performance measurement:
the characterization method of the eutectic compound performance comprises the following steps:
diffuse reflectance spectrum: setting the wavelength range to be 200-800nm and the slit to be 4nm, placing 100mg of the obtained eutectic compound into a sample cell, and then placing into an Agilent Carry 5000 instrument for testing;
solid fluorescence spectrum: setting excitation wavelength at 570nm, emission wavelength range at 580-800nm and slit at 2nm, placing 100mg of obtained eutectic compound in sample cell, and placing in FLS9800 instrument for detection;
fluorescence lifetime: setting the excitation wavelength as 570nm, the emission wavelength as 659nm, the slit as 5nm and the number of collected points as 5000, placing 100mg of the obtained eutectic compound into a sample cell, and then placing into an FLS9800 instrument for detection.
Specifically, FIG. 4 shows a eutectic compound, rhodamine 6G and [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]Diffuse reflectance spectrum of molecular clusters, from which can be seen [ N (C 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]The molecular cluster has a broad absorption peak in the ultraviolet region of 200-400nm, while the eutectic compound has a broad absorption peak in the ultraviolet visible region of 200-600nm, indicating rhodamine 6G and [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]Molecular cluster complexing was successful and [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]The absorption spectrum of the molecular cluster can be expanded from the ultraviolet region to the visible region through the combination with the organic fluorescent dye molecules, and the application of the molecular cluster is expected to be expanded.
From the fluorescence spectra, as shown in fig. 5-6, the left side of fig. 5 shows a fluorescence emission pattern of rhodamine 6G under 365nm ultraviolet lamp irradiation, and it can be seen from the graph that rhodamine 6G hardly fluoresces, and the right side of fig. 5 shows a fluorescence emission pattern of eutectic compound under 365nm ultraviolet lamp irradiation, and it can be seen from the graph that the eutectic compound can emit strong red fluorescence. FIG. 6 is a graph of fluorescence spectra of the eutectic compound and rhodamine 6G of the present invention, both having emission wavelengths of about 650nm at an excitation wavelength of 570nm, and further, the fluorescence intensity of the eutectic compound is enhanced by approximately 14 times compared to rhodamine 6G.
Fig. 7 and 8 are graphs of fluorescence lifetime of rhodamine 6G and eutectic compound, respectively, and it can be seen that both fluorescence lifetimes are in the ns range, both decreasing with double indices, but the fluorescence lifetime of the eutectic compound is significantly greater than rhodamine 6G.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (7)
1. A eutectic compound with solid state fluorescence performance is characterized in that the chemical molecular formula of the eutectic compound is { [ C ] 28 H 31 ClN 2 O 3 ] 2 [N(C 4 H 9 ) 4 ] 2 }[α-Mo 8 O 26 ]The molecular structure is shown as formula 1:
formula 1.
2. A method of preparing a eutectic compound having solid state fluorescence properties according to claim 1, comprising the steps of:
I. synthesis of [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]Precursor: moO is carried out 3 And [ ("A")n-C 4 H 9 ) 4 N]Stirring the OH aqueous solution at room temperature to obtain a white milk-like substance, filtering, vacuum drying, dissolving in acetonitrile, and crystallizing in a refrigerator;
II. The [ N (C) 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]Dissolving in acetonitrile, adding rhodamine 6G dissolved in an organic solvent to obtain a yellow solution, and volatilizing the solvent to obtain the eutectic compound with solid fluorescence.
3. The method according to claim 2, wherein in the step I, moO is selected from the group consisting of 3 And [ ("A")n-C 4 H 9 ) 4 N]The molar ratio of OH was 2:1.
4. The method of claim 3, wherein the stirring time in step I is 60-h and the vacuum drying time is 10-20-h.
5. The method according to claim 2, wherein in step ii, [ N (C 4 H 9 ) 4 ] 4 [α-Mo 8 O 26 ]And rhodamine 6G in a molar ratio of 2:1 to 8:1.
6. The method according to claim 2, wherein the organic solvent in step II comprises acetonitrile, methanol,N,N’Dimethylformamide or dichloromethane.
7. Use of a eutectic compound with solid state fluorescence properties according to claim 1 for the preparation of temperature sensors, pressure sensors, concentration sensors, gas sensors, electrochemical sensors, electroluminescent devices.
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| AU2021101799A AU2021101799A4 (en) | 2021-02-04 | 2021-04-08 | Eutectic compound with solid fluorescence property and preparation method and application thereof |
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| WO2019157376A1 (en) * | 2018-02-09 | 2019-08-15 | Massachusetts Institute Of Technology | Molybdenum oxo alkylidene compounds, methods of making the same and use thereof in metathesis reactions |
| CN111841639A (en) * | 2020-06-22 | 2020-10-30 | 嘉兴学院 | Europium complex with function of catalyzing photodegradation of organic dye and preparation method and application thereof |
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| WO2019157376A1 (en) * | 2018-02-09 | 2019-08-15 | Massachusetts Institute Of Technology | Molybdenum oxo alkylidene compounds, methods of making the same and use thereof in metathesis reactions |
| CN111841639A (en) * | 2020-06-22 | 2020-10-30 | 嘉兴学院 | Europium complex with function of catalyzing photodegradation of organic dye and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
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| Controlled assembly and reversible transformation of tuneable luminescent Mo8-R6G hybrids;Hui-Min Zeng，等;《Inorg. Chem. Front.》;第第9卷卷(第第1期期);第78-82页 * |
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