CN115403598A - Photosensitive semiconductor material and preparation method and application thereof - Google Patents
Photosensitive semiconductor material and preparation method and application thereof Download PDFInfo
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- CN115403598A CN115403598A CN202210454838.2A CN202210454838A CN115403598A CN 115403598 A CN115403598 A CN 115403598A CN 202210454838 A CN202210454838 A CN 202210454838A CN 115403598 A CN115403598 A CN 115403598A
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- 239000000463 material Substances 0.000 title claims abstract description 26
- 239000004065 semiconductor Substances 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 229910052709 silver Inorganic materials 0.000 claims abstract description 12
- 239000004332 silver Substances 0.000 claims abstract description 12
- AUXDIUGCNUFQEM-UHFFFAOYSA-N 2-(2-pyridin-3-ylethenyl)pyridine Chemical compound C=1C=CN=CC=1C=CC1=CC=CC=N1 AUXDIUGCNUFQEM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000013078 crystal Substances 0.000 claims description 12
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 10
- AUXDIUGCNUFQEM-VOTSOKGWSA-N 2-[(e)-2-pyridin-3-ylethenyl]pyridine Chemical group C=1C=CN=CC=1/C=C/C1=CC=CC=N1 AUXDIUGCNUFQEM-VOTSOKGWSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 239000008367 deionised water Substances 0.000 claims description 5
- 229910021641 deionized water Inorganic materials 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims description 5
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 239000003446 ligand Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000007106 1,2-cycloaddition reaction Methods 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229920001795 coordination polymer Polymers 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/10—Silver compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention discloses a photosensitive semiconductor material and a preparation method and application thereof, wherein the photosensitive semiconductor material is a complex 1- [ (1- (2-pyridyl) -2- (3-pyridyl) ethene) (1, 3-phthalic acid radical) 0.5 Silver (Ag)] n The electric conductivity of the complex is 26.8 +/-1.2S-cm ‑1 . The photosensitive semiconductor material generates complex 2- (1, 3-di (2-pyridyl) -2, 4-di (3-pyridyl)) -cyclobutane under the radiation of ultraviolet light 0.5 (1, 3-Benedicarboxylic acid radical) 0.5 Silver (Ag)] n The conductivity of the complex 2 was 39.1. + -. 1.1 S.cm ‑1 Compared with the complex 1, the conductivity is improved by 46 percent. The synthesis method of the photosensitive semiconductor material is simple, the synthesis conditions are mild, and the photosensitive semiconductor material can be produced in a large scale.
Description
Technical Field
The invention belongs to the technical field of semiconductor materials, and particularly relates to a photosensitive semiconductor material and a preparation method and application thereof.
Background
In recent years, functional complex materials have been receiving increasing attention in various fields. The functional complex shows wide application prospect in the fields of light, electricity, magnetism, adsorption separation, drug slow release, molecular switch and the like. The inorganic-organic hybrid functional complex has good designability of structure and high thermal stability. Since metal ions and organic ligands are widely varied, complexes formed by the coordination self-assembly reaction thereof exhibit various structures. As is well known, the structure determines the nature, and among numerous complex structures, a substance of a specific structure has its corresponding nature. The formation process and structure of the complex can be controlled by selecting the metal salt, the ligand and the reaction conditions, and the purpose of regulating and controlling the properties of the product is finally realized. At present, the research on the relationship between the design and synthesis, structure and performance of the complex is one of the leading directions of inorganic chemistry, and it spans multiple subject fields such as chemistry, crystal engineering, material science and life science.
The number of reported complexes is not very large, but after most of the functional complexes are synthesized, the structure is not changed. The minority coordination polymer can be structurally changed when being stimulated by the outside, and the structural change is usually accompanied with the change of material properties. Organic ligands containing olefinic bonds can be arranged in parallel at a close distance under the regulation and control of coordinate bonds, and can generate [2+2] cycloaddition reaction under the irradiation of ultraviolet light to generate the derivatives of the cyclobutane. Some properties of the newly formed complex can be greatly changed due to the change of the structure of the complex, including the change of conditions such as the conjugation property of the ligand, the stacking mode, the distance of metal-metal bonds, the charge arrangement and the like.
Disclosure of Invention
The invention provides a photosensitive semiconductor material and a preparation method and application thereof, wherein the photosensitive semiconductor material is [ (1- (2-pyridyl) -2- (3-pyridyl) ethene) (1, 3-phthalic acid radical) 0.5 Silver (Ag)] n And n is the number of repeating units and is any positive integer. The preparation method of the complex is simple and the reaction conditions are mild. Under the catalysis of ultraviolet light, the conductivity of the material is obviously improved.
The photosensitive semiconductor material is a complex 1- (2-pyridyl) -2- (3-pyridyl) ethylene) (1, 3-phthalic acid radical) 0.5 Silver (Ag)] n And n is the number of repeating units and is any positive integer.
Wherein the structural formulas of the 1- (2-pyridyl) -2- (3-pyridyl) ethene and the 1, 3-benzenedicarboxylates are respectively shown as follows:
the crystal of the complex 1 belongs to a monoclinic system, the space group is C2/C, and the unit cell parameter is
α＝90°，β＝103.46(3)°，γ＝90°。
The preparation method of the photosensitive semiconductor material comprises the following steps:
dissolving 1- (2-pyridyl) -2- (3-pyridyl) ethylene, 1, 3-phthalic acid and silver nitrate in a mixed solvent of deionized water and acetonitrile, adjusting the pH value of the solution to be between 5 and 6, and reacting to obtain the photosensitive semiconductor material.
Further, the synthesis method is a solvent thermal synthesis method.
Further, the molar ratio of the 1- (2-pyridyl) -2- (3-pyridyl) ethylene to the 1, 3-phthalic acid to the silver nitrate is 1-2: 1 to 2:1 to 2, preferably 2:1:2.
further, the volume ratio of the deionized water to the acetonitrile mixed solvent is V Water (I) :V Acetonitrile (ACN) =4 to 5:1, preferably 4:1.
further, the pH of the system is adjusted to 5-6 by a nitric acid solution, the concentration of the nitric acid solution may be 0.1M, and preferably, the pH is adjusted to 6.
Further, the reaction temperature is 165-175 ℃, and the reaction time is 24-30h; preferably, the reaction temperature is 175 ℃ and the reaction time is 24h.
The application of the photosensitive semiconductor material is that ultraviolet light with the wavelength of 365nm is adopted to irradiate the complex 1, so that the electric conductivity of the material is improved.
Specifically, the complex 1 crystal is placed under an LED ultraviolet lamp with the light-emitting wavelength of 365nm for illumination, and then the complex 2- (1, 3-di (2-pyridyl) -2, 4-di (3-pyridyl)) -cyclobutane) can be obtained 0.5 (1, 3-Benzenedicarboxylic acid radical) 0.5 Silver (Ag)] n 。
The crystal of the complex 2 belongs to a monoclinic system, the space group is C2/C, and the unit cell parameter is
α＝90°，β＝107.92(3)°，γ＝90°。
The detection proves that the conductivity of the complex 1 is 26.8 +/-1.2S-cm -1 The conductivity of the complex 2 was 39.1. + -. 1.1 S.cm -1 The conductivity of the complex 2 is improved by 46 percent compared with that of the complex 1.
The preparation method has the advantages of simple process, mild reaction conditions and high light conversion rate.
Drawings
FIG. 1 shows complex 1- [ (1- (2-pyridyl) -2- (3-pyridyl) ethylene) (1, 3-benzenedicarboxylate) 0.5 Silver (Ag)] n Crystal structure of (2).
FIG. 2 is a nuclear magnetic resonance spectrum of the complex 1.
FIG. 3 is a powder X-ray diffraction pattern of Complex 1.
FIG. 4 shows complex 2- [ (1, 3-bis (2-pyridyl) -2, 4-bis (3-pyridyl)) -cyclobutane) 0.5 (1, 3-Benedicarboxylic acid radical) 0.5 Silver] n Crystal structure of (2).
FIG. 5 is a nuclear magnetic resonance spectrum of the complex 2.
FIG. 6 is a powder X-ray diffraction pattern of Complex 2.
Detailed Description
Non-limiting examples are described below:
1. complex 1- (2-pyridyl) -2- (3-pyridyl) ethene) (1, 3-benzenedicarboxylate) 0.5 Silver (Ag)] n Preparation of
1- (2-pyridyl) -2- (3-pyridyl) ethylene 1.82g (10 mmol), 1, 3-phthalic acid 0.83g (5 mmol), silver nitrate 1.70g (10 mmol) and mixed solvent 25mL (deionized water 20mL, acetonitrile 5 mL) were added to a 50mL reaction vessel and the pH of the solution was adjusted to 6 with 0.1M nitric acid solution. Sealing the reaction kettle, placing the reaction kettle at the constant temperature of 175 ℃ for 24 hours, slowly cooling to room temperature after the reaction is finished to obtain colorless crystals, filtering, washing, collecting crystalline compounds, and airing at room temperature to obtain the complex 1 with the yield: 2.53g, yield: 68 percent. The crystallographic parameters are as follows:
crystallographic parameters of complex 1: c 16 H 12 N 2 O 2 Ag,M r ＝372.15,Monoclinic,space group C2/c,
α＝90°,β＝103.46(3)°,γ＝90°,
Z＝8,D c ＝1.864g cm -3 ,μ＝1.525mm -1 ,23265reflections measured,3041unique reflections(R int ＝0.0216),2840observed reflections(I>2σ(I)),191parameters,R 1 ＝0.0267,wR 2 ＝0.0674,S＝1.128。
The structure of the X-ray single crystal of the complex 1 is shown in figure 1.
The NMR spectrum of complex 1 is shown in FIG. 2.
The powder X-ray diffraction spectrum of complex 1 is shown in FIG. 3.
2. Complex 2- [ (1, 3-bis (2-pyridyl) -2, 4-bis (3-pyridyl)) -cyclobutane) 0.5 (1, 3-Benzenedicarboxylic acid radical) 0.5 Silver] n Preparation of (2)
Placing the complex 1 (0.19g and 0.5mmol) in a culture dish, and then placing the culture dish under an LED ultraviolet lamp (20W) with the light-emitting wavelength of 365nm at a distance of 5cm for 10 minutes to obtain a complex 2, wherein the yield is as follows: 0.19g, yield: 100 percent.
The crystallographic parameters are as follows:
crystallographic parameters of complex 2: c 16 H 12 N 2 O 2 Ag,M r ＝372.15,Monoclinic,space group C2/c,
α＝90°,β＝107.92(3)°,γ＝90°,
Z＝8,D c ＝1.828g cm -3 ,μ＝1.495mm -1 ,28524reflections measured,3114unique reflections(R int ＝0.0413),2577observed reflections(I>2σ(I)),191parameters,R 1 ＝0.0342,wR 2 ＝0.0638,S＝1.160。
The X-ray single crystal structure of complex 2 is shown in FIG. 4.
The NMR spectrum of complex 2 is shown in FIG. 5.
The powder X-ray diffraction spectrum of complex 2 is shown in FIG. 6.
3. Conductivity of Complex 1 and Complex 2
The test shows that the conductivity of the complex 1 is 26.8 +/-1.2S-cm -1 In complex 1, the distance of Ag. Cndot. Ag is
The conductivity of the complex 2 is 39.1 +/-1.1S-cm -1 The distance of Ag in the complex 2 is
The conductivity of complex 2 was improved by 46% compared to complex 1. When the olefin ligand in the complex 1 undergoes cycloaddition reaction, the distance between the central metal silver is shortened, the bond length of Ag & Ag bond is shortened obviously, and the conductivity of the complex 2 is improved obviously.
Claims (10)
1. A photosensitive semiconductor material, characterized by:
the photosensitive semiconductor material is complex 1- [ (1- (2-pyridyl) -2- (3-pyridyl) ethene) (1, 3-benzene dicarboxylic acid radical) 0.5 Silver (Ag)] n N is the number of repeating units and is any positive integer;
wherein the structural formulas of the 1- (2-pyridyl) -2- (3-pyridyl) ethylene and the 1, 3-benzenedicarboxylates are respectively shown as follows:
2. the photosensitive semiconductor material of claim 1, wherein:
the crystal of the complex 1 belongs to a monoclinic system, the space group is C2/C, and the unit cell parameter is
α＝90°，β＝103.46(3)°，γ＝90°。
3. A method for preparing a photosensitive semiconductor material according to claim 1 or 2, comprising the steps of:
dissolving 1- (2-pyridyl) -2- (3-pyridyl) ethylene, 1, 3-phthalic acid and silver nitrate in a mixed solvent consisting of deionized water and acetonitrile, adjusting the pH value of the solution to be between 5 and 6, and reacting to obtain the photosensitive semiconductor material.
4. The production method according to claim 3, characterized in that:
the mol ratio of the 1- (2-pyridyl) -2- (3-pyridyl) ethylene to the 1, 3-phthalic acid to the silver nitrate is (1-2): 1 to 2:1 to 2.
5. The production method according to claim 3, characterized in that:
the volume ratio of the deionized water to the acetonitrile in the mixed solvent is V Water (W) :V Acetonitrile ＝4～5：1。
6. The production method according to claim 3, characterized in that:
the pH value of the system is adjusted to 5-6 by nitric acid solution, and the concentration of the nitric acid solution is 0.1M.
7. The production method according to claim 3, characterized in that:
the reaction temperature is 165-175 ℃, and the reaction time is 24-30h.
8. Use of a photosensitive semiconductor material according to claim 1 or 2, characterized in that:
ultraviolet light with the wavelength of 365nm is adopted to irradiate the complex 1, so that the electric conductivity of the material is improved.
9. Use according to claim 8, characterized in that:
placing the crystal of complex 1 under 365nm LED ultraviolet lamp to obtain complex 2- (1, 3-di (2-pyridyl) -2, 4-di (3-pyridyl)) -cyclobutane) 0.5 (1, 3-Benzenedicarboxylic acid radical) 0.5 Silver (Ag)] n And n is the number of repeating units and is any positive integer.
10. Use according to claim 9, characterized in that:
the crystal of the complex 2 belongs to a monoclinic system, the space group is C2/C, and the unit cell parameter is
α＝90°，β＝107.92(3)°，γ＝90°。
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116120573A (en) * | 2022-12-19 | 2023-05-16 | 淮阴师范学院 | Coordination polymer material and preparation method and application thereof |
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| CN116120573A (en) * | 2022-12-19 | 2023-05-16 | 淮阴师范学院 | Coordination polymer material and preparation method and application thereof |
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