CN114685530B - Aggregation-induced emission molecule based on isoquinoline and preparation method thereof - Google Patents
Aggregation-induced emission molecule based on isoquinoline and preparation method thereof Download PDFInfo
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- CN114685530B CN114685530B CN202210323964.4A CN202210323964A CN114685530B CN 114685530 B CN114685530 B CN 114685530B CN 202210323964 A CN202210323964 A CN 202210323964A CN 114685530 B CN114685530 B CN 114685530B
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- 238000004220 aggregation Methods 0.000 title claims abstract description 20
- 230000002776 aggregation Effects 0.000 title claims abstract description 20
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 7
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 10
- 229940125904 compound 1 Drugs 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical group [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 2
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims description 2
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000000463 material Substances 0.000 abstract description 7
- 239000007850 fluorescent dye Substances 0.000 abstract description 3
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- YCFAYUBODIMYEU-UHFFFAOYSA-N 1,2,2,3,4,5-hexakis-phenylsilole Chemical compound C1(=CC=CC=C1)C1(C(=C(C(=[Si]1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 YCFAYUBODIMYEU-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000006617 triphenylamine group Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
Abstract
The invention discloses an aggregation-induced emission molecule based on isoquinoline and a preparation method thereof. The fluorescent probe knotThe structure is shown in the formula I, and the O-alkynyl aromatic aldehyde is used as a raw material and is subjected to condensation reaction with 2-aminobenzyl alcohol to obtain the O-alkynyl aromatic aldehyde. The aggregation-induced emission molecules obtained by the method are simple to synthesize, mild in condition and high in yield. The aggregation-induced emission molecule has practical application value in the fields of biochemistry, functional molecular materials and the like.
Description
Technical Field
The invention relates to the field of synthesis of organic functional molecules, in particular to an aggregation-induced emission molecule based on isoquinoline and a preparation method thereof.
Background
The effect of fluorescence imaging depends to a large extent on the nature of the fluorescent material. Conventional fluorescent materials are susceptible to aggregation resulting in quenching (ACQ), and the fluorescence intensity at high concentrations or in the polymerized state is weaker than that in solution. In addition, in the visual tracking process of images, the traditional fluorescent material has poor photo-bleaching resistance and strong background signal, so that false positive results are caused, and the fluorescent material is not suitable for long-term tracking and imaging. These drawbacks have hampered the use of traditional fluorescent materials in the biomedical field, and a new class of fluorescent molecules is needed for substitution.
At the beginning of the century, the Tang Benzhong group observed that hexaphenylsilacyclopentadiene had a propeller-type molecular conformation, which did not fluoresce in solution, and emitted blue fluorescence when aggregates formed, thus suggesting the concept of aggregation-induced emission (AIE). Due to limited intramolecular rotation or intramolecular vibration, AIE molecules fluoresce strongly under solid or high concentration excitation light, but do not fluoresce in solution or dissolved state, contrary to ACQ molecule phenomenon. The discovery of the AIE phenomenon has led to the research interest of scientists in the world's chemistry, materials, etc., who have synthesized a variety of different AIE molecules, such as styrenes, acrylonitriles, heterocyclopentadienes, pyrans, triphenylamines, fluoroborons, and intramolecular hydrogen bonding compounds. AIE is widely used in chemistry, biosensors, cell imaging, and OLEDs due to its special optical properties.
Disclosure of Invention
Aiming at the technical problems, the invention provides an aggregation-induced emission molecule based on isoquinoline and a preparation method thereof.
The technical scheme of the invention is as follows:
an isoquinoline-based aggregation-induced emission molecule has a structure shown in a formula (I):
（I）
wherein, R group is hydrogen, halogen atom, alkyl or alkoxy.
The preparation method of the aggregation-induced emission molecule based on isoquinoline comprises the following steps:
dissolving a compound 1 and a proper amount of 2-aminobenzyl alcohol in an organic solvent, adding a certain amount of catalyst, wherein the amount ratio of the compound 1 to the 2-aminobenzyl alcohol is 1:3-1:1, the amount of the catalyst is 5% -100% of that of the compound 1, stirring for 2-24 hours at a certain temperature, completely separating out solids, filtering, and recrystallizing a crude product with absolute ethyl alcohol to obtain a light yellow solid compound I; namely, an aggregation-induced emission molecule represented by the formula (I).
The above compounds are identified by the following numbers for each compound in the reaction scheme.
Further, in the synthesis step, the ratio of the amounts of the substances of the compound 1 and 2-aminobenzyl alcohol is preferably 1:1.
Further, in the synthesis step, the catalyst is preferably silver nitrate, silver triflate or silver trifluoroacetate.
Further, in the synthesis step, the organic solvent is preferably absolute ethanol.
The invention has the beneficial effects that:
(1) The invention provides a new aggregation-induced emission molecule, and provides a candidate substance for research of fluorescent functional materials.
(2) The invention provides a simple and efficient synthesis method of aggregation-induced emission molecules.
Drawings
FIG. 1 is a graph showing fluorescence spectra of aggregation-induced emission molecules prepared in example 2 of the present invention in tetrahydrofuran-water solutions in different ratios, wherein the top-down curves represent fluorescence curves of the fluorescent molecules in tetrahydrofuran-water solutions of 1:99, 1:9, 2:8, 3:7, 5:5, 6:4, 7:3, 8:2, and 9:1, respectively.
In fig. 1, the abscissa represents wavelength (wavelength), and the ordinate represents intensity (intensity).
Detailed Description
The present invention will be described in further detail by way of specific examples, but it should not be construed that the scope of the above subject matter of the present invention is limited to the following examples. All techniques implemented based on the above description of the invention are within the scope of the invention.
The invention uses the instrument and the reagent:
nuclear magnetic resonance apparatus: bruker AV-II 500 MHz NMR, TMS as internal standard, CDCl 3 Is a solvent.
The reagents used were all commercially available chemically pure or analytically pure.
Example 1
Synthesis of fluorescent probes of the invention
The preparation method of the fluorescent probe comprises the following steps:
into a dry, closed-tube reactor, 0.2 mmole of 1 was added followed by 0.22 mmole of o-aminobenzyl alcohol and 10% of AgNO equivalent 3 Finally, adding 2 mL of EtOH as a solvent, sealing, adding a small magnetite, placing into an oil bath at 80 ℃ for stirring and refluxing for 12 hours, performing TLC tracking reaction, washing out the mixture by using ethyl acetate after the basic reaction is completed, adding a proper amount of silica gel powder, spin-drying, recrystallizing by using hot ethanol, purifying, and filtering to obtain a yellow solid product I. The products of the different substituents R are represented by Ia, ib, ic, id, ie and the like.
(R is methoxy), yellow solid, IR (KBr) cm -1 3416, 2923, 1617, 1510, 1252, 1176, 1030, 700, 622. 1 H NMR (500 MHz, CDCl 3 )δ7.031-6.980 (m, 16H), 6.940-6.985 (m, 4H), 6.846-6.806 (m, 2H), 6.724 (t,J= 7.5 Hz, 1H), 6.671 (d,J= 8.5 Hz, 2H), 6.168 (d,J= 8 Hz, 1H), 5.700 (s, 2H), 5.062 (d,J= 15 Hz, 1H), 4.924 (d,J= 15 Hz, 1H), 3.687 (s, 3H). 13 C NMR (125 MHz, CDCl 3 )δ144.2, 143.9, 141.2, 141.0, 140.8, 140.7, 140.3, 132.5, 131.7, 131.6, 131.5, 130.9, 130.4, 130.0, 129.6, 128.6, 128.0,127.7, 126.6, 126.6, 126.4, 125.8, 125.7, 124.8, 124.3, 123.6, 122.8, 113.5, 104.5, 84.9, 68.0, 55.3. HRMS: C 43 H 34 NO 2 for [M + H] + , Calculated 596.2590; found 596.2584.
Ib (R is methyl), yellow solid IR (KBr) cm -1 3427, 2923, 1606, 1491, 1444, 1283, 824, 751, 700, 630. 1 H NMR (500 MHz, CDCl 3 )δ7.053-6.980 (m, 16H), 6.944-6.898 (m, 6H), 6.848-6.811 (m, 2H), 6.716 (t,J= 7.5 Hz, 1H), 6.164 (d,J= 8.5 Hz, 1H), 5.717 (d,J= 6 Hz, 2H), 5.072 (d,J= 14.5 Hz, 1H), 4.935 (d,J= 15 Hz, 1H), 2.227 (s, 3H). 13 C NMR (125 MHz, CDCl 3 )δ144.1, 143.8, 141.2, 141.1, 140.7, 140.6, 140.2, 137.6, 134.1, 132.4, 131.6, 131.4, 131.2, 130.7, 130.3, 128.7, 128.5,127.9, 127.6, 126.5, 126.5, 126.3, 125.7, 125.5, 124.7, 124.2, 123.6, 122.7, 104.7, 84.8, 67.9, 21.3. HRMS: C 43 H 34 NO for [M + H] + , Calculated 580.2640; found 580.2635.
Ic (R is hydrogen), yellow solid Mp. -123 ℃ IR (KBr) cm -1 3436, 2924, 1599, 1491, 1444, 1283, 1029, 762, 700, 635. 1 H NMR (400 MHz, CDCl 3 )δ7.123-7.092 (m, 16H), 7.044-6.995 (m, 6H), 6.936-6.917 (m, 3H), 6.794 (t,J= 7.6 Hz, 1H), 6.233 (d,J= 8 Hz, 1H), 5.828 (d,J= 7.6 Hz, 2H), 5.183 (d,J= 14.8 Hz, 1H), 5.044 (d,J= 14.8 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 )δ144.0, 143.8, 141.4, 141.1, 140.7, 140.5, 140.1, 137.1, 132.5, 131.7, 131.4, 130.6, 130.4, 128.7, 128.6, 128.0, 127.9, 127.8, 127.7, 126.5, 126.5, 126.3, 125.7, 125.5,124.7, 124.2, 123.7, 122.9, 104.9, 84.8, 68.0. HRMS: C 42 H 32 NO for [M + H] + , Calculated 566.2484; found 566.2478.
Id (R is fluorine), yellow solid IR (KBr) cm -1 3422, 2974, 2924, 1623, 1507, 1491, 1283, 1226, 1076, 1048, 880, 750, 700. 1 H NMR (500 MHz, CDCl 3 )δ7.039-6.982 (m, 16H), 6.942-6.909 (m, 4H), 6.868-6.807 (m, 4H), 6.732 (t,J= 8 Hz, 1H), 6.121 (d,J= 8.5 Hz, 1H), 5.698 (s, 2H), 5.082 (d,J= 15 Hz, 1H), 4.940 (d,J= 15 Hz, 1H). 13 C NMR (125 MHz, CDCl 3 )δ144.1, 143.9, 143.8, 141.6, 140.9, 140.6, 140.2, 140.0, 133.2, 132.6, 131.7, 131.5, 131.0, 130.5, 130.5, 129.0, 128.8, 128.0, 127.8,127.7, 126.6, 126.6, 126.4, 125.7, 124.9, 124.3, 123.7, 123.2, 115.2 (d,J= 21.5 Hz), 105.0, 84.9, 68.1.HRMS: C 42 H 31 FNO for [M + H] + , Calculated 584.2390; found 584.2384.
Ie (R is chlorine), yellow solid IR (KBr) cm -1 3423, 2923, 1618, 1491, 1443, 1407, 1283, 1090, 836, 750, 700. 1 H NMR (400 MHz, CDCl 3 )δ7.116-7.087 (m, 16H), 7.042-7.006 (m, 6H), 6.969-6.913 (m, 2H), 6.844 (t,J= 7.6 Hz, 1H), 6.226 (d,J= 8.4 Hz, 1H), 5.813 (d,J= 8 Hz, 2H), 5.172 (d,J= 14.8 Hz, 1H), 5.032 (d,J= 14.8 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 )δ144.0, 143.8, 143.7, 141.7, 140.9, 140.5, 139.8, 135.6, 133.7, 132.5, 131.6, 131.4, 130.4,130.3, 129.9, 128.6, 128.3, 127.9, 127.7, 127.7, 126.6, 126.5, 126.4, 125.8, 124.9, 124.1, 123.8, 123.1, 105.4, 84.7, 68.0. HRMS: C 42 H 31 ClNO for [M + H] + , Calculated 600.2094; found 600.2089.
Example 2
Fluorescence spectrum of fluorescent molecule Ie in tetrahydrofuran-water solution with different ratio
Taking a standard tetrahydrofuran solution of Ie, preparing tetrahydrofuran-water solution containing tetrahydrofuran in the ratio of 1:99, 1:9, 2:8, 3:7, 5:5, 6:4, 7:3, 8:2 and 9:1 with water, keeping the concentration of Ie at 10 micromoles per liter all the time, and respectively recording the change of fluorescence intensity at 500 and nm by a fluorescence spectrometer. The fluorescence intensity is plotted on the ordinate and the emission wavelength on the abscissa, and the change curve of the fluorescence intensity is shown in FIG. 1.
Claims (4)
1. An isoquinoline-based aggregation-induced emission molecule is characterized by having a structure represented by formula (I):
wherein, R group is H, cl, F, OMe, me.
2. The method for preparing the isoquinoline-based aggregation-induced emission molecules according to claim 1, comprising the steps of:
dissolving a compound 1 and a proper amount of 2-aminobenzyl alcohol in an organic solvent, adding a certain amount of catalyst, wherein the catalyst is selected from silver nitrate, silver triflate or silver trifluoroacetate, the amount ratio of the compound 1 to 2-aminobenzyl alcohol substances is 1:3-1:1, the dosage of the catalyst is 5% -100% of that of the compound 1, stirring for 2-24 hours at a certain temperature, completely separating out solids, filtering, and recrystallizing a crude product with absolute ethyl alcohol to obtain a light yellow solid compound I; namely, an aggregation-induced emission molecule represented by the formula (I).
3. The method for preparing an isoquinoline based aggregation-induced emission molecule according to claim 2, wherein the amount of the substances of the compound 1 and 2-aminobenzyl alcohol in the synthesis step is 1:1.
4. The method for preparing an aggregation-induced emission molecule according to claim 2, wherein the organic solvent is methanol or ethanol in the synthesis step.
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| CN103896825A (en) * | 2014-04-17 | 2014-07-02 | 东南大学 | 9,10-diarylethene anthracene (CPASA) aggregation-induced light emitting molecule and preparation method thereof |
| CN113278000A (en) * | 2021-05-28 | 2021-08-20 | 大连大学 | Coumarin-based red light aggregation-induced luminescent material and preparation method thereof |
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| CN103896825A (en) * | 2014-04-17 | 2014-07-02 | 东南大学 | 9,10-diarylethene anthracene (CPASA) aggregation-induced light emitting molecule and preparation method thereof |
| CN113278000A (en) * | 2021-05-28 | 2021-08-20 | 大连大学 | Coumarin-based red light aggregation-induced luminescent material and preparation method thereof |
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