CN115626936A - Synthesis method of complex luminescent material capable of finely regulating and controlling luminescent wavelength - Google Patents
Synthesis method of complex luminescent material capable of finely regulating and controlling luminescent wavelength Download PDFInfo
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- CN115626936A CN115626936A CN202211407540.2A CN202211407540A CN115626936A CN 115626936 A CN115626936 A CN 115626936A CN 202211407540 A CN202211407540 A CN 202211407540A CN 115626936 A CN115626936 A CN 115626936A
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- 239000000463 material Substances 0.000 title claims abstract description 32
- 230000001105 regulatory effect Effects 0.000 title claims abstract description 20
- 238000001308 synthesis method Methods 0.000 title claims abstract description 15
- 230000001276 controlling effect Effects 0.000 title claims abstract description 9
- 239000003446 ligand Substances 0.000 claims abstract description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- 238000006467 substitution reaction Methods 0.000 claims abstract description 7
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical group C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 238000012360 testing method Methods 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 230000002194 synthesizing effect Effects 0.000 claims description 9
- 238000005303 weighing Methods 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 238000006862 quantum yield reaction Methods 0.000 claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 claims description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000000295 emission spectrum Methods 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 238000002390 rotary evaporation Methods 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 14
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000004020 luminiscence type Methods 0.000 abstract 1
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 230000004075 alteration Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic System without C-Metal linkages
-
- 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
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- 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
Abstract
The invention discloses a synthesis method of a complex luminescent material for finely regulating and controlling luminescent wavelength, relates to the technical field of luminescent materials, and changes different substitution positions R of methyl on phenanthridine ring 1 、R 2 、R 3 And R 4 To obtain four ligands L with different luminescence wavelengths 1‑4 (ii) a Wherein the methyl group is in position R 1 Corresponding ligand L when singly substituted 1 Methyl in position R 2 Corresponding to ligand L when singly substituted 2 Methyl in position R 3 Corresponding to ligand L when singly substituted 3 Methyl in position R 4 Corresponding to ligand L when singly substituted 4 . The synthesis method of the complex luminescent material for finely regulating the luminescent wavelength comprises the following steps: by changing the same substituent at different positions of the functional molecule, i.e. changing the methyl group at the phenanthridine ring, four luminescent complexes with different luminescent wavelengths are obtained, andit was found that the limited rotation of the substituents changes the photophysical properties of the luminescent complexes, which may provide a new way of thinking for the design and synthesis of luminescent materials with high luminous efficiency.
Description
Technical Field
The invention relates to the technical field of luminescent materials, in particular to a synthesis method of a complex luminescent material for finely regulating and controlling luminescent wavelength.
Background
Luminescent materials developed from transition metal luminescent complexes are extremely important and common luminescent materials, and have wide application in the fields of biomedicine, photochemical identification and sensing and the like.
In the prior art, most of the existing methods for improving the luminous efficiency of transition metal complexes are complex methods for designing novel ligands and mixing metal doping, so that the development of a simple and effective method for improving the luminous efficiency of transition metal complexes is very important.
Therefore, the ligand with isomeric substituent positions is designed and synthesized, the wavelength of emitted light is regulated and controlled by changing the substituent position of a methyl group, the luminescent performance of the complex is successfully regulated and controlled by utilizing the isomeric substituent positions, and a new thought is provided for designing and synthesizing the luminescent material of the transition metal complex.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a synthesis method of a complex luminescent material for finely regulating and controlling luminescent wavelength, so as to solve the problems in the background technology.
In order to achieve the purpose, the invention provides the following technical scheme: a process for synthesizing the complex as luminous material with fine regulation of luminous wavelength features that the methyl group is substituted at different positions R of phenanthridine ring 1 、R 2 、R 3 And R 4 To obtain four different corresponding ligands L 1-4 ；
Wherein the methyl group is in position R 1 Corresponding to ligand L when singly substituted 1 Methyl in position R 2 Corresponding to ligand L when singly substituted 2 Methyl in position R 3 Corresponding to ligand L when singly substituted 3 Methyl in position R 4 Corresponding ligand L when singly substituted 4 ；
The synthesis method comprises the following steps:
s1, weighing 10mmol of 2-aminobiphenyl and derivatives thereof, 10mmol of 2-aldehyde quinoline and 0.50mL of trifluoroacetic acid, and dissolving in 30mL of N, N-dimethylformamide;
s2, reacting the reactant in the step S1 at 140 ℃ for 48 hours, and cooling to room temperature;
s3, pouring the reaction mixture cooled in the step S2 into 300mL of distilled water, and adjusting the pH value;
s4, extracting the aqueous solution based on dichloromethane, and combining organic phases;
s5, drying based on anhydrous magnesium sulfate, carrying out suction filtration, and removing the solvent by rotary evaporation to obtain a crude product;
s6, separating the crude product in the step S5 by silica gel column chromatography to obtain a ligand L 1-4 ；
S7, weighing the ligand L according to the molar ratio of 1 1-4 And the corresponding metal salts Zn (NO) 3 ) 2 6H 2 O；
S8, mixing the ligand in the step S7 and the corresponding metal salt, dissolving the mixture in an acetonitrile solution, and ultrasonically mixing the mixture to form a complex solution [ ZnL ] 1-4 (NO 3 ) 2 ]；
S9, p-complex [ ZnL 1-4 (NO 3 ) 2 ]Testing is carried out;
s10, analyzing based on the test result, wherein [ ZnL ] is 1-4 (NO 3 ) 2 ]The most suitable complex for the luminescent material is selected.
Further optimizing the technical scheme, in the step S3, the pH value is adjusted to 9-10 by adding saturated sodium bicarbonate solution.
In the step S4, the weighing amount of dichloromethane is 50mL, and the number of times of extraction is three.
Further optimizing the technical scheme, in the step S6, the obtained ligand L is subjected to 1-4 The yield calculation is carried out to obtain the ligand L 1-3 Yield and ligand L 4 The yield of (a).
Further optimizing the technical scheme, in the step S9, the test content includes an emission spectrum, a fluorescence lifetime and a quantum yield of the test complex.
Compared with the prior art, the invention provides a synthesis method of a complex luminescent material for finely regulating and controlling luminescent wavelength, which has the following beneficial effects:
according to the synthesis method of the complex luminescent material for finely regulating the luminescent wavelength, the substitution position of methyl is changed by a simple method of changing the same substituent at different positions of a functional molecule, the wavelength of emitted light is regulated, the regulation of the luminescent performance of the complex is realized by successfully utilizing the position isomerism of the substituent, four luminescent complexes with different luminescent efficiencies are obtained, and the luminescent efficiency of the complex is reduced when the rotation of the substituent is limited, so that a new thinking path is provided for designing and synthesizing the luminescent material with high luminescent efficiency.
Drawings
FIG. 1 shows a ligand L of a synthesis method of a complex luminescent material for finely regulating and controlling a luminescent wavelength provided by the invention 1 -4 Synthesizing a path diagram;
FIG. 2 shows a synthetic method of a [ ZnL ] complex luminescent material for finely regulating and controlling luminescent wavelength according to the present invention 1-4 (NO 3 ) 2 ]The fluorescence emission spectrum of the complex is normalized.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The first embodiment is as follows:
referring to fig. 1, a method for synthesizing a complex luminescent material with a fine-tuning luminescent wavelength by changing the R position of methyl at different substituted positions of phenanthridine ring 1 、R 2 、R 3 And R 4 To obtain four different corresponding ligands L 1-4 。
Wherein the methyl group is in position R 1 When singly substituted, correspond toBody L 1 Methyl in position R 2 Corresponding to ligand L when singly substituted 2 Methyl in position R 3 Corresponding to ligand L when singly substituted 3 Methyl in position R 4 Corresponding ligand L when singly substituted 4 。
The synthesis method comprises the following steps:
s1, weighing 10mmol of 2-aminobiphenyl and its derivatives, 10mmol of 2-aldehyde quinoline and 0.50mL of trifluoroacetic acid (i.e., TFA in FIG. 1) and dissolving in 30mL of N, N-dimethylformamide (i.e., DMF in FIG. 1).
And S2, reacting the reactants in the step S1 at 140 ℃ for 48h, and cooling to room temperature.
And S3, pouring the reaction mixture cooled in the step S2 into 300mL of distilled water, and adjusting the pH value to 9-10 by adding saturated sodium bicarbonate solution.
S4, extracting the aqueous solution three times based on 50mL of dichloromethane, and combining organic phases.
And S5, drying based on anhydrous magnesium sulfate, performing suction filtration, and performing rotary evaporation to remove the solvent to obtain a crude product.
S6, separating the crude product in the step S5 by silica gel column chromatography to obtain a ligand L 1-4 To the resulting ligand L 1-4 The yield calculation is carried out to obtain the ligand L 1-3 Yield of about 45% and ligand L 4 The yield of (a) was about 8%.
S7, weighing the ligand L according to the molar ratio of 1 1-4 And the corresponding metal salt Zn (NO) 3 ) 2 6H 2 O。
S8, mixing the ligand in the step S7 and the corresponding metal salt, dissolving the mixture in an acetonitrile solution, and ultrasonically mixing the mixture to form a complex solution [ ZnL ] 1-4 (NO 3 ) 2 ]。
S9, p-complex [ ZnL 1-4 (NO 3 ) 2 ]Tests were performed including emission spectra, fluorescence lifetimes and quantum yields of the test complexes.
Wherein, FIG. 2 is [ ZnL ] 1-4 (NO 3 ) 2 ]The results of the normalized fluorescence emission spectra of the complexes, the fluorescence lifetime of the complexes and the quantum yield are shown in table 1.
TABLE 1[ 2 ], [ ZnL ] 1-4 (NO 3 ) 2 ]Fluorescence lifetime and quantum yield of the complexes
S10, analyzing based on the test result, wherein [ ZnL ] is 1-4 (NO 3 ) 2 ]The most suitable complex for the luminescent material is selected.
Example two:
complex [ ZnL ] is carried out based on the synthesis method of the complex luminescent material for finely regulating the luminescent wavelength described in the embodiment one 1-4 (NO 3 ) 2 ]The synthesis of (1) obtains four luminescent complexes with different emission wavelengths by changing different substitution positions of methyl on a phenanthridine ring, and the data in table 1 are combined to find that the fluorescence lifetime of all complexes can be obtained by fitting a linear equation and corresponds to the single-exponential fluorescence lifetime, and the situation shows that only one luminescent center exists in the complexes. And the substituents being in the edge position [ ZnL ] 1 (NO 3 ) 2 ]Complexes and [ ZnL ] 4 (NO 3 ) 2 ]The light quantum yield of the complex is lowest, namely the corresponding luminous efficiency is lower than that of the other two complexes, researches show that when methyl rotation is limited during substitution of the position, the luminous efficiency is reduced, and simultaneously, people can find that [ ZnL ] is 2 (NO 3 ) 2 ]The light quantum yield of the complex is 64%, the luminous efficiency is high, and the emission wavelength belongs to the blue light range, so that the complex has great potential to be developed into a blue light material. In conclusion, four luminescent complexes with different emission wavelengths and different luminescent efficiencies are obtained by utilizing position isomerism of the substituent, and meanwhile, the fact that the luminescent efficiency of the complexes is reduced when the rotation of the substituent is limited is summarized, so that a new idea is provided for improving the luminescent efficiency of the complexes.
The invention has the beneficial effects that:
according to the synthesis method of the complex luminescent material for finely regulating the luminescent wavelength, the substitution position of methyl is changed by a simple method of changing the same substituent at different positions of a functional molecule, the wavelength of emitted light is regulated, the regulation of the luminescent performance of the complex is realized by successfully utilizing the position isomerism of the substituent, four luminescent complexes with different luminescent efficiencies are obtained, and the luminescent efficiency of the complex is reduced when the rotation of the substituent is limited, so that a new thinking path is provided for designing and synthesizing the luminescent material with high luminescent efficiency.
In the description of the specification, reference to the description of "one embodiment," "some embodiments," "an example," "a specific example," or "some examples" or the like means that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above are not necessarily intended to refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples. Moreover, various embodiments or examples and features of various embodiments or examples described in this specification can be combined and combined by one skilled in the art without being mutually inconsistent.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that various changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (5)
1. A synthesis method of a complex luminescent material for finely regulating and controlling luminescent wavelength is characterized in that different substitution positions R of methyl on phenanthridine ring are changed 1 、R 2 、R 3 And R 4 To obtain four different corresponding ligands L 1-4 ；
Wherein the methyl group is in position R 1 Corresponding to ligand L when singly substituted 1 Methyl in position R 2 Corresponding ligand L when singly substituted 2 Methyl in position R 3 Corresponding ligand L when singly substituted 3 Methyl in position R 4 Corresponding ligand L when singly substituted 4 ；
The synthesis method comprises the following steps:
s1, weighing 10mmol of 2-aminobiphenyl and derivatives thereof, 10mmol of 2-aldehyde quinoline and 0.50mL of trifluoroacetic acid, and dissolving in 30mL of N, N-dimethylformamide;
s2, reacting the reactant in the step S1 at 140 ℃ for 48 hours, and cooling to room temperature;
s3, pouring the reaction mixture cooled in the step S2 into 300mL of distilled water, and adjusting the pH value;
s4, extracting the aqueous solution based on dichloromethane, and combining organic phases;
s5, drying based on anhydrous magnesium sulfate, carrying out suction filtration, and removing the solvent by rotary evaporation to obtain a crude product;
s6, separating the crude product in the step S5 by silica gel column chromatography to obtain a ligand L 1-4 ；
S7, weighing the ligand L according to the molar ratio of 1 1-4 And the corresponding metal salt Zn (NO) 3 ) 2 6H 2 O；
S8, mixing the ligand in the step S7 and the corresponding metal salt, dissolving the mixture in an acetonitrile solution, and ultrasonically mixing the mixture to form a complex solution [ ZnL ] 1-4 (NO 3 ) 2 ]；
S9, p-complex [ ZnL ] 1-4 (NO 3 ) 2 ]Testing is carried out;
s10, analyzing based on the test result in [ ZnL ] 1-4 (NO 3 ) 2 ]The most suitable complex for the luminescent material is selected.
2. The method for synthesizing the complex luminescent material for finely regulating the luminescent wavelength according to claim 1, wherein in the step S3, the pH value is adjusted to 9-10 by adding a saturated sodium bicarbonate solution.
3. The method for synthesizing the complex luminescent material for finely regulating the luminescent wavelength according to claim 1, wherein in the step S4, the weighing amount of dichloromethane is 50mL, and the number of times of extraction is three.
4. The method for synthesizing the complex luminescent material for finely regulating the luminescent wavelength according to claim 1, wherein in the step S6, the obtained ligand L is subjected to 1-4 The yield calculation is carried out to obtain the ligand L 1-3 Yield and ligand L 4 The yield of (a).
5. The method as claimed in claim 1, wherein in step S9, the test contents include an emission spectrum, a fluorescence lifetime, and a quantum yield of the test complex.
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| CN202211407540.2A CN115626936B (en) | 2022-11-10 | Synthesis method of complex luminescent material capable of finely regulating and controlling luminescence wavelength |
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| CN202211407540.2A CN115626936B (en) | 2022-11-10 | Synthesis method of complex luminescent material capable of finely regulating and controlling luminescence wavelength |
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| CN115626936B CN115626936B (en) | 2024-05-17 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115785131A (en) * | 2022-11-15 | 2023-03-14 | 五邑大学 | Synthetic method of high-efficiency luminescent complex material with tunable luminescent wavelength |
| CN115785131B (en) * | 2022-11-15 | 2024-05-17 | 五邑大学 | Method for synthesizing high-efficiency luminescent complex material with tunable luminescent wavelength |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101225297A (en) * | 2007-12-14 | 2008-07-23 | 华南理工大学 | Metal complex having emission wavelength regulation property and preparation thereof |
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101225297A (en) * | 2007-12-14 | 2008-07-23 | 华南理工大学 | Metal complex having emission wavelength regulation property and preparation thereof |
Non-Patent Citations (1)
| Title |
|---|
| INES STARKE ET AL.: "Complexation of diazaperylene and bisisoquinoline with transition metal ions in the gas phase studied by electrospray ionization mass spectrometry", RAPID COMMUNICATIONS IN MASS SPECTROMETRY, pages 665 - 671 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115785131A (en) * | 2022-11-15 | 2023-03-14 | 五邑大学 | Synthetic method of high-efficiency luminescent complex material with tunable luminescent wavelength |
| CN115785131B (en) * | 2022-11-15 | 2024-05-17 | 五邑大学 | Method for synthesizing high-efficiency luminescent complex material with tunable luminescent wavelength |
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