CN114671855B - Acridine ligand for photo-thermal material, cuprous iodide cluster-based coordination polymer with photo-thermal property, and preparation method and application thereof - Google Patents
Acridine ligand for photo-thermal material, cuprous iodide cluster-based coordination polymer with photo-thermal property, and preparation method and application thereof Download PDFInfo
- Publication number
- CN114671855B CN114671855B CN202210432107.8A CN202210432107A CN114671855B CN 114671855 B CN114671855 B CN 114671855B CN 202210432107 A CN202210432107 A CN 202210432107A CN 114671855 B CN114671855 B CN 114671855B
- Authority
- CN
- China
- Prior art keywords
- cui
- dpa
- cluster
- cuprous iodide
- photo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000013256 coordination polymer Substances 0.000 title claims abstract description 76
- 229910021595 Copper(I) iodide Inorganic materials 0.000 title claims abstract description 66
- 229920001795 coordination polymer Polymers 0.000 title claims abstract description 34
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 title claims abstract description 30
- 239000003446 ligand Substances 0.000 title abstract description 26
- 238000002360 preparation method Methods 0.000 title abstract description 5
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 title description 12
- 239000000463 material Substances 0.000 title description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- WFKITCAYPQWCEA-UHFFFAOYSA-N 2,7-dipyridin-4-ylacridine Chemical compound C(C(C1=CC=NC=C1)=CC1=CC2=C3)=CC1=NC2=CC=C3C1=CC=NC=C1 WFKITCAYPQWCEA-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 23
- 238000001816 cooling Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000003384 imaging method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000003672 processing method Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002184 metal Substances 0.000 abstract description 4
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 229910021645 metal ion Inorganic materials 0.000 abstract description 3
- 239000010949 copper Substances 0.000 description 29
- 238000000634 powder X-ray diffraction Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000001144 powder X-ray diffraction data Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000001237 Raman spectrum Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical class I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000002447 crystallographic data Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004896 high resolution mass spectrometry Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- MGAAUJYLQGQIOK-UHFFFAOYSA-N 2,7-dibromoacridine Chemical compound C1=CC(Br)=CC2=CC3=CC(Br)=CC=C3N=C21 MGAAUJYLQGQIOK-UHFFFAOYSA-N 0.000 description 1
- OGNCVVRIKNGJHQ-UHFFFAOYSA-N 4-(3-pyridin-4-ylpropyl)pyridine Chemical compound C=1C=NC=CC=1CCCC1=CC=NC=C1 OGNCVVRIKNGJHQ-UHFFFAOYSA-N 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 241000700196 Galea musteloides Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013257 coordination network Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- XYVDNBKDAAXMPG-UHFFFAOYSA-M decyl 2-(1-heptylazepan-1-ium-1-yl)acetate;hydroxide Chemical compound [OH-].CCCCCCCCCCOC(=O)C[N+]1(CCCCCCC)CCCCCC1 XYVDNBKDAAXMPG-UHFFFAOYSA-M 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- KDMWFFHKQUJBLB-UHFFFAOYSA-N n-methyl-1,1-diphenylpropan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(C)NC)C1=CC=CC=C1 KDMWFFHKQUJBLB-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000012634 optical imaging Methods 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 239000012221 photothermal agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000985 reflectance spectrum Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000004729 solvothermal method Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/001—Macromolecular compounds containing organic and inorganic sequences, e.g. organic polymers grafted onto silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
-
- 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
- C09K3/00—Materials not provided for elsewhere
-
- 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
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
Abstract
A cuprous iodide cluster-based coordination polymer with photo-thermal property, a preparation method and application thereof, wherein CuI and 2, 7-di (pyridine-4-yl) acridine are mixed with a solvent to obtain the cuprous iodide cluster-based coordination polymer. The synthesized ligand DPA is utilized, and the alpha-, beta-and gamma-CuI-DPA with different space topological structures can be prepared by only adjusting the proportion of metal and ligand, and the synthesized three cuprous iodide cluster-based coordination polymers are used for the first time, so that CPs with different space topological structures are built on the basis of the same molecular block for the first time; in synthetic gamma-CuI-DPA, there is rare [ Cu ] 2 I 2 ]The three-dimensional structure constructed by six links provides a charge transport channel for gamma-CuI-DPA, so that the conductivity and the photo-thermal conversion efficiency are higher than those of alpha-CuI-DPA and beta-CuI-DPA, and a foundation is laid for designing and preparing conductive CPs with metal ion chains.
Description
Technical Field
The invention relates to the technical field of functional materials, in particular to an acridine ligand for a photo-thermal material, a cuprous iodide cluster-based coordination polymer with photo-thermal property, a preparation method and application thereof.
Background
Coordination polymers (Coordination polymers, CPs) are self-assembled molecular assemblies, and can be assembled into one-dimensional, two-dimensional or three-dimensional networks through regulating metal ions, organic ligands and synthesis condition groups to obtain unique structures and functions, so that the high-crystallinity materials can be applied to gas adsorption, catalysis, sensors, biological imaging, optoelectronics and the like. Based on copper iodide clusters ([ CuI)] n ) Not only does the CPs of (1) produce a superior topology due to the multi-core structure, but also brings unique properties to the crystalline material such as luminescence, conductivity, and photocatalysis.
In the current research, the research group of Li designed and synthesized a series of inorganic-organic hybrid materials composed of [ Cu ] based on different ligands 4 I 4 ]One, two, three-dimensional expansions of the structure and a strong network. Lang's group constructed [ Cu-based ] in different solvent systems using the same ligand 1, 3-bis (4-pyridyl) propane 2 I 2 ]-and [ Cu ] 4 I 4 ]Is a CPs of (C). However, in the prior art, coordination polymers constructed based on different molecular blocks have never been reported for constructing CPs with different spatial topologies based on the same molecular block, which also hinders researchers from exploring the possibility of relationship between the structure and performance of different CuI-CPs with similar molecular components.
Disclosure of Invention
The invention aims to overcome the defect that the prior art lacks related researches on constructing CPs with different space topological structures based on the same molecular block, and provides an acridine ligand for a photo-thermal material, a cuprous iodide cluster-based coordination polymer with photo-thermal property, and a preparation method and application thereof.
The aim of the invention is achieved by the following technical scheme:
an acridine ligand for photo-thermal material is 2, 7-di (pyridine-4-yl) acridine.
A processing method of cuprous iodide cluster-based coordination polymer with photo-thermal property comprises the steps of mixing CuI and 2, 7-di (pyridine-4-yl) acridine with a solvent, heating to react, and cooling to obtain a solid, namely the cuprous iodide cluster-based coordination polymer.
Preferably, the molar ratio of the CuI to the 2, 7-di (pyridin-4-yl) acridine is 1:10-10:1.
Preferably, the reaction temperature is 120-150 ℃.
Preferably, the temperature is reduced to 18-50 ℃.
Preferably, the solvent is one or more of tetrahydrofuran, acetone, ethyl acetate, chloroform, ethanol, N-dimethylformamide and acetonitrile.
A cuprous iodide cluster-based coordination polymer with photothermal properties, comprising at least one of α -CuI-DPA, β -CuI-DPA, and γ -CuI-DPA.
Preferably, the cuprous iodide cluster-based coordination polymer is α -CuI-DPA when the molar ratio of CuI to 2, 7-bis (pyridin-4-yl) acridine is 1:1;
when the molar ratio of CuI to 2, 7-di (pyridin-4-yl) acridine is 2:1, the cuprous iodide cluster-based coordination polymer is beta-CuI-DPA;
when the molar ratio of CuI to 2, 7-bis (pyridin-4-yl) acridine is 4:1, the cuprous iodide cluster-based coordination polymer is gamma-CuI-DPA.
Use of cuprous iodide cluster-based coordination polymer with photo-thermal properties in photo-thermal imaging.
The invention has the following advantages:
1. the synthesized ligand 2, 7-di (pyridine-4-yl) acridine (DPA) is utilized, and the alpha-, beta-and gamma-CuI-DPA with different space topological structures can be prepared only by adjusting the proportion of metal and the ligand, so that the synthesized three cuprous iodide cluster-based coordination polymers are used for the first time, and CPs with different space topological structures are built based on the same molecular block for the first time.
2. In synthetic gamma-CuI-DPA, there is rare [ Cu ] 2 I 2 ]Six-linked three-dimensional structures, the unique chains provide charge transport channels for the gamma-CuI-DPA three-dimensional structure, resulting in conductivity (-10) -6 S m -1 ) And the light-heat conversion efficiency (. Eta.) 808nm And (23%) is higher than alpha-CuI-DPA and beta-CuI-DPA, and lays a foundation for designing and preparing conductive CPs with metal ion chains.
3. In addition, the synthesized gamma-CuI-DPA also has higher photo-thermal conversion efficiency, and plays an important role in promoting non-radiative migration and triggering photo-thermal conversion.
4. The technology related to constructing different CPs by using the same molecular block provides a potential research object for researching and analyzing the structure-performance relationship of the CPs, and also opens the way for synthesizing novel photo-thermal conversion CPs or conductive CPs.
Drawings
FIG. 1 shows a scheme for DPA synthesis.
Fig. 2 is a graph of copper iodide cluster-based coordination polymers (mode of attachment of asymmetric ligands to three cuis and spatial structure along the axis) formed in different proportions for CuI and DPA.
FIG. 3 is a view of the spatial structure of the α -CuI-DPA along (a) b-axis and (b) c-axis, and the laminate (c).
Fig. 4 is a PXRD analysis and comparison chart.
PXRD analysis of samples reacted in different CuI-DPA proportions; c-d simulation of alpha-, beta-, and gamma-CuI-DPA and comparison of experimental PXRD results.
Fig. 5 is a view of the spatial structure of β -CuI-DPA along (a) b-axis and (b) c-axis, and the stack (c).
Fig. 6 is a view of the spatial structure of γ -CuI-DPA along (a) b-axis and (b) c-axis, and stacked layers (c).
Fig. 7 is an X-ray diffraction (PXRD) analysis of three synthetic powders.
FIG. 8 is a schematic diagram of the gamma-CuI-DPA production and conversion process.
(a) The structure of gamma-CuI-DPA can be seen as three chains interwoven together; (b) a simplified three-dimensional spatial structure; (c) interconversion patterns between three CPs.
FIG. 9 FT-IR (a) and Raman spectra (b) of DPA and three CPs
FIG. 10 shows variable temperature PXRD (a-c) and thermogravimetric analysis (d) of alpha-, beta-and gamma-CuI-DPA
Fig. 11 is a PXRD analysis used to study solvent stability. (a) alpha-CuI-DPA, (b) beta-CuI-DPA and (c) gamma-CuI-DPA
FIG. 12 is a graph showing performance testing of three CPs.
(a) Ultraviolet-visible-near infrared solid absorption spectra of three CPs and reactants (DPA and CuI); (b) Photocurrent response, (c) I-V plot and (d) energy level plot of α -, β -and γ -CuI-DPA. (e) Photothermal conversion curve of CPs powder during three cycles of heating and cooling (806 nm,1.0Wcm -2 10 mg). (f) Near infrared laser (806 nm,1.5 Wcm) -2 ,0.2mL,50mgmL -1 ) The photothermal reaction to the aqueous CPs suspension is followed by turning off the laser.
FIG. 13 shows the application of three CPs in photothermography
(a) An optical camera photograph; (b-d) photothermographic photographs (α -CuI-DPA on the outside and γ -CuI-DPA on the inside); (b) no illumination; (c) a xenon lamp light source; (d) a xenon lamp source with a 750nm long pass filter.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. The components of the embodiments of the present invention generally described and illustrated in the figures herein may be arranged and designed in a wide variety of different configurations.
Thus, the following detailed description of the embodiments of the invention, as presented in the figures, is not intended to limit the scope of the invention, as claimed, but is merely representative of selected embodiments of the invention. All other embodiments, based on the embodiments of the invention, which are apparent to those of ordinary skill in the art without inventive faculty, are intended to be within the scope of the invention.
In addition, the embodiments of the present invention and the features of the embodiments may be combined with each other without collision.
It should be noted that: like reference numerals and letters denote like items in the following figures, and thus once an item is defined in one figure, no further definition or explanation thereof is necessary in the following figures.
General materials and methods
All reagents were purchased from energy chemical industry (Shanghai, china) and used as such unless otherwise indicated. Nuclear magnetic resonance spectra were recorded using an AVANCED RX400 nuclear magnetic resonance spectrometer (Bruker, germany) operating at 400 MHz. High Resolution Mass Spectrometry (HRMS) was measured by an Agilent 6540Q-TOF mass spectrometer (Agilent, usa). Fourier transform infrared (FT-IR) spectrum is obtained by using a Thermo Nicolet spectrometer and KBr particles (Thermo Nicolet 365) at 4000-400cm -1 Recorded in range. The Raman spectrum is 2000-200cm -1 Using high resolution in the range of (2)The evolution instrument (LABRAM HR EVO, horiba, japan) was recorded under laser excitation at 633 nm. TGA was performed under an N2 atmosphere using a Mettler-Toledo 1600LF instrument with a heating rate of 10deg.C/min -1 . The PXRD structure was prepared by Smartlab SE X-ray diffractometer (Rigaku, japan) with Cu K at 40kV and 200mA α Radiation shooting, scanning speed of 20 DEG min -1 The step size is 0.02 °. The specific surface area was measured by the BET method using nitrogen adsorption/desorption at 77K.
Example 1:
the embodiment provides a processing method of a cuprous iodide cluster-based coordination polymer with photo-thermal property, which comprises the steps of mixing CuI and ligand 2, 7-di (pyridine-4-yl) acridine with a solvent, heating to 120-150 ℃ for reaction, and then cooling to below 50 ℃, wherein the temperature is preferably 18-25 ℃ at room temperature, and the precipitated solid is the cuprous iodide cluster-based coordination polymer, wherein the cuprous iodide cluster-based coordination polymer comprises at least one of alpha-CuI-DPA, beta-CuI-DPA and gamma-CuI-DPA; wherein the solvent is one or more of tetrahydrofuran, acetone, ethyl acetate, chloroform, ethanol, N-dimethylformamide and acetonitrile, preferably N, N-dimethylformamide and acetonitrile; the molar ratio of CuI to 2, 7-di (pyridin-4-yl) acridine is 1:10-10:1:
when the molar ratio of CuI to 2, 7-di (pyridin-4-yl) acridine is 1:1, the cuprous iodide cluster-based coordination polymer is alpha-CuI-DPA;
when the molar ratio of CuI to 2, 7-di (pyridin-4-yl) acridine is 2:1, the cuprous iodide cluster-based coordination polymer is beta-CuI-DPA;
when the molar ratio of CuI to 2, 7-bis (pyridin-4-yl) acridine is 4:1, the cuprous iodide cluster-based coordination polymer is gamma-CuI-DPA.
Example 2:
synthesis of novel ligand 2, 7-di (pyridin-4-yl) acridine (DPA)
Ligand DPA is synthesized by suzuki coupling, and the specific scheme is shown in figure 1:
(1) a solution of benzyltriethylammonium bromide (TEBA, 12 g, 44 mmol) in methanol (100 ml) was added to acridine (2.16 g, 12 mmol). The reaction was then stirred at 60℃for 16 hours with a reflux condenser. After cooling to room temperature, the crude product was filtered and washed with a small amount of pyridine and dichloromethane. After evaporation in vacuo at 50℃2, 7-dibromoacridine was obtained as a pale yellow solid.
(2) 2, 7-dibromoacridine (0.67 mg, 2.0 mmol), pyridine-4-boronic acid (0.59 g, 2.4 mol), csF (2.8 g, 18 mmol) and Pd (PPh) 3 ) 4 (0.130 g, 0.12 mmol) in dimethoxymethane (40 ml) in N 2 Stirring for 3 days at 90℃under an atmosphere. And the crude product was purified by chromatography (methanol/chloroform=1:50) to give a yellow powder (0.3 g, yield 45%).
Example 3:
synthesis of novel CuI-DPA
(1) Let 1 through CuI and DPA: 1 to synthesize alpha-CuI-DPA. CuI (0.012 g, 0.06 mmol) and DPA (0.019 g, 0.06 mmol) were added to a solution of N, N "-dimethylformamide (DMF, 4 ml) and acetonitrile (4 ml). The mixture was stirred at room temperature for several minutes, then poured into a 25 ml teflon lined stainless steel vessel, heated to 120 ℃ for 48 hours, cooled to room temperature, and after which the red bulk crystals were collected, yield: 56% based on CuI.
(2) The ratio of CuI to DPA was 2:1 to synthesize beta-CuI-DPA. CuI (0.024 g, 0.12 mmol) and DPA (0.019 g, 0.06 mmol) were added to a solution of DMF (4 ml) and acetonitrile (4 ml). The mixture was stirred at room temperature for several minutes, then poured into a 25 ml teflon lined stainless steel vessel, heated to 120 ℃ for 48 hours, cooled to room temperature and the dark red rod-like crystals collected. Yield: 58% based on CuI.
(3) The ratio of CuI to DPA was 4:1 to synthesize gamma-CuI-DPA. CuI (0.24 g, 0.12 mmol) and DPA (0.010 g, 0.03 mmol) were added to a solution of DMF (4 ml) and acetonitrile (4 ml). The mixture was stirred at room temperature for several minutes, then poured into a 25 ml teflon lined stainless steel vessel, heated to 150 ℃ for 48 hours, cooled to room temperature and the brown bulk crystals collected. Yield: 57% based on CuI.
The solvent in this embodiment is a mixture of N, N '-dimethylformamide and acetonitrile, and may be replaced by N, N' -dimethylformamide or acetonitrile or other solvents, and the total amount of the solvent may be 2 mL, 4 mL, 6 mL, 8 mL, 10 mL, 12 mL, 14 mL, 16 mL, 18 mL or more, and the reactant in the preferred system is 3-4.5 mg/mL, and the different concentrations of the reactant and the product may affect the reaction rate and the collection difficulty of the product. The heating time in this example is preferably 24 to 60 hours in consideration of the yield of the product, the balance of the reaction, and the continuous conversion between the various crystal forms of the product in the system.
1 test and characterization of cuprous iodide Cluster-based coordination Polymer
1.1 Crystal Structure
The ratio of metal to ligand, solvent environment, bridging ligand and counter anion structure, and even numerous factors such as reaction temperature and pH will result in (CuI) n The difference in clusters means that when CuI-based complexes are synthesized, a slight difference may result in the formation of different derivatives. In this study, therefore, various synthesis conditions were explored to selectively obtain pure compounds. A high quality single crystal suitable for single crystal X-ray diffraction analysis was obtained by solvothermal method in a mixed solvent of acetonitrile and DMF. Table 1 lists the main crystallographic data of all CPs. Different synthesis ratios of CuI and DPA lead to [ Cu ] with different coordination modes 2 I 2 ]Based on a structure, i.e. based on analogous [ Cu ] 2 I 2 ]1-dimensional, 2-dimensional, 3-dimensional CPs (1D-, 2D-, and 3D-CPs) of structures and DPA ligands, see in particular FIG. 2.
TABLE 1 crystallographic data of CPs
FIGS. 2 and 3 show the single crystal X-ray diffraction structure of alpha-CuI-DPA and show that alpha forms a 1D structure at P2 1 Crystallization in n space group. The asymmetric unit comprises one DPA molecule and half of [ Cu ] 2 I 2 ]Structure is as follows. Adjacent [ Cu ] 2 I 2 ]The structure is linked by two DPA ligands. [ Cu ] 2 I 2 ]The structure shows planar four coordination and is attached to the pyridinyl-N of DPA. However, acridine-N in DPA is uncoordinated, DPA ligands are linked as banana-like binary ligands [ Cu2I2]And (3) forming a one-dimensional extension chain. While chains are stacked together by weak interactions at a distance of 3.5The sliding distance is 7.5 +.>The layers are formed in one direction as in fig. 4, and then the layers are stacked to form alpha crystals with an angle of 52.3 deg. between them.
Structural analysis of beta-CuI-DPA shows that a two-dimensional coordination network is formed and at P2 1 Crystallization in n space group as shown in FIGS. 2 and 5. While the asymmetric unit comprises one [ Cu ] 2 I 2 ]A structure and a DPA ligand. Unlike α, [ Cu ] in β 2 I 2 ]The structure shows a three-coordinate, whereas DPA is also a three-plane coordinate. [ Cu ] due to steric hindrance of acridine-N in DPA 2 I 2 ]One Cu (I) in the structure is singly coordinated to acridine-N via a Cu-N bond, while the other Cu (I) is linked to two pyridyl-N groups of the DPA ligand. Thus, a three-connection [ Cu ] 2 I 2 ]Is linked to three DPA ligands, extending to form a planar two-dimensional network. Adjacent layers are antiparallel at a distance of 3.6Beta crystals are formed as shown in figure 4.
gamma-CuI-DPA crystallizes in the P-1 space group and the coordination appears to be more complex, see fig. 2 and 6. Likewise, [ Cu ] can be observed 2 I 2 ]SBUs, but coordinate in a three-dimensional six-way rather than planar. I atoms not only co-ordinating with Cu (I) to form [ Cu ] 2 I 2 ]SBUs, and also joined by another Cu (I) (Cu 4) to form [ (Cu) 2 I 2 )Cu]A chain. And [ Cu ] 2 I 2 ]Cu (I) (Cu 1 andcu 5) is connected to DPA with pyridinyl-N. [ Cu ] 4 (CN) 4 ]Two Cu (I) (Cu) 2 And Cu 3 ) The three chains together form a three-dimensional gamma crystal linked to DPA with acridinyl-N, as shown in FIG. 4.
1.2 interconversion
Three stable phases were found during the synthesis in the metal ligand ratio range from 1:10 to 10:1 according to powder X-ray diffraction (PXRD) analysis, see (a) in fig. 7. Further screening gave an optimal CuI-to-DPA ratio of 1: 1. 2:1 and 4:1 and the resulting samples were designated α -CuI-DPA, β -CuI-DPA and γ -CuI-DPA, respectively. The PXRD pattern showed that the CPs as synthesized were pure phase, as was the case with the simulated patterns of these three CPs, see (b) - (c) in fig. 7. As shown in FIG. 8, when the same amount of CuI was added to the α -CuI-DPA in DMF/acetonitrile reaction mixture and the reaction system was subjected to additional solvothermal treatment, β -CuI-DPA was produced, as demonstrated by the PXRD structure, as shown in FIG. 9. This means that α -CuI-DPA can be converted to β -CuI-DPA. Further experiments confirm successful interconversions between α -, β -and γ -CuI-DPA. Furthermore, these results indicate that interconversion can occur between CuI or DPA when they are added precisely to achieve ratios that meet the conditions for formation of another CPs in the α -, β -or γ -CuI-DPA system.
1.3 characterization
The CPs obtained in FIG. 9 were characterized by Fourier transform infrared (FT-IR) spectra, and the differences between CPs and DPA in FT-IR spectra showed coordination effects. As for Raman spectroscopy, the complexation effect was also further confirmed.
The thermal stability of these CPs was studied by temperature swing PXRD and thermogravimetric analysis (TGA) as shown in figure 10. The alpha-, beta-and gamma-CuI-DPA all show good thermal stability. Meanwhile, we tested the solvent stability in various common solvents, and the results are shown in fig. 11. CPs were soaked in different solvents for three days, and the PXRD patterns of alpha-and gamma-CuI-DPA soaked in different solvents were not significantly changed, indicating good solvent stability. However, the PXRD pattern for β -CuI-DPA varies slightly in some solvents and can be recovered after soaking in DMF.
The UV-Vis-NIR absorption of CuI-DPA CPs becomes more intense than the ligand, the absorption range produces a red shift with intense visible light absorption. As shown in FIG. 12 (a), the diffuse reflectance spectrum shows that the absorption of CuI and DPA is mainly in the ultraviolet region (270-410 nm), while the absorption of CuI is also strong in the near infrared (1700 nm). The near infrared absorption of gamma-CuI-DPA is stronger and wider than that of beta-CuI-DPA, while alpha-CuI-DPA is the weakest of the three CPs. Alpha-and beta-CuI-DPA have strong absorption in the ultraviolet to visible region (220-570-nm).
1.4 Electrical Properties
Among materials formed from inorganic and organic components, electrical conduction is well understood, but their combination to produce a conductive CPs network is an emerging, rapidly evolving field of research. As shown in FIGS. 12 (b) - (c), the strongest photocurrent response of gamma-CuI-DPA (-0.5. Mu.A cm) -2 ) And the highest conductivity (-10-6S m) -1 ) Meaning that more free charge carriers are generated under illumination and electron transport is easier. For alpha-and beta-CuI-DPA they show a weak photocurrent response (0.1-0.15. Mu.A cm -2 ) And low conductivity (-10-8S m) -1 ). These results indicate that three-dimensional gamma-CuI-DPA has better photocurrent response and conductivity than one-dimensional alpha-and two-dimensional beta-CuI-DPA. As shown in (d) of fig. 12, HOMO levels of the three CPs do not change much, and LUMO levels vary with different topologies of CPs. gamma-CuI-DPA enjoys the narrowest electronic bandgap (eg=1.40 eV) and lowest LUMO level (elumo= -3.34 eV), whereas alpha-and beta-CuI-DPA exhibit wider electronic bandgaps (eg=1.90 eV and 1.65 eV) and higher LUMO levels (elumo= -3.07eV and-2.97 eV).
1.5 photothermal conversion
Light-to-heat conversion materials have attracted increasing attention over the last decades, and many such materials have been utilized by scientists. Planar DPA stacks in CuI-DPA CPs networks with varying degrees of non-covalent interactions have been pointed out as important factors in promoting non-radiative migration and initiating photothermal conversion. However, these three CPs consisting of two luminescent components, DPA and CuI, do not show a range from visible to visible under UV or visible light irradiationNear infrared emission. Therefore, cuI-DPA has the potential as a photothermal material. As shown in FIG. 12 (e), the photothermal conversion curve of these CPs powders after three heating and cooling cycles directly shows that the CuI-DPA powder was laser-irradiated at 808nm (1.0W cm) -2 ) Lower photo-thermal capability. Under near infrared irradiation, the temperatures of α -, β -and γ -CuI-DPA rise rapidly from room temperature (22 ℃) and stabilize at 68 ℃, 118 ℃ and 183 ℃ respectively in 180 seconds. For further quantitative comparison, the photothermal conversion efficiency of the aqueous dispersion was measured using water as a heat conducting medium. The temperature of the dispersion of these CPs (10 mg dispersed in 0.2 ml water) was increased under irradiation with 808nm laser light. According to the cooling curve at the time of turning off the laser, as in (f) of fig. 12, α -CuI-DPA shows a small temperature rise (Δt=10.4 ℃, from 21.0 to 31.4 ℃) corresponding to 8.6% of the photothermal conversion efficiency, whereas β -CuI-DPA has a slightly higher temperature rise (Δt=15.1 ℃, from 21.0 to 36.1 ℃) of the photothermal conversion efficiency of 11.5%. Interestingly, γ -CuI-DPA showed a significant temperature rise (Δt=53.1 ℃, from 21.0 ℃ to 74.1 ℃) with a corresponding photo-thermal conversion efficiency of 23.9%.
Example 4:
application of
These CPs with photothermal conversion characteristics are potential photothermal agents and can be applied to photothermal imaging. Photothermal imaging is lossless, with higher imaging resolution and deeper imaging penetration than optical imaging. We produced Chinese tobacco LOGO with α -and γ -CuI-DPA, respectively. And light of different wavelengths is used to illuminate the letter structure through Xe lamps with different optical filters. Corresponding to their absorption spectra, α -and γ -CuI-DPA have strong absorption in the visible light band, and show indistinguishable brightness in photothermal images, as in (b) of fig. 13. When irradiated with visible light, both portions have luminance which is difficult to distinguish in a photothermal image, as in (c) - (d) in fig. 13. When irradiated with near infrared light, a clear pattern appears on the round card, as shown in fig. 13 (a). Therefore, under the light irradiation of different wavelengths, the photothermal conversion imaging can be realized through the photothermal conversion.
Although the present invention has been described with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications may be made to the embodiments described, or equivalents may be substituted for elements thereof, and any modifications, equivalents, improvements and changes may be made without departing from the spirit and principles of the present invention.
Claims (4)
1. A processing method of a cuprous iodide cluster-based coordination polymer with photo-thermal property is characterized in that: mixing CuI and 2, 7-di (pyridine-4-yl) acridine with a solvent, heating to 120-150 ℃ for reaction, and cooling to 18-50 ℃ to obtain a solid which is the cuprous iodide cluster-based coordination polymer;
the molar ratio of the CuI to the 2, 7-di (pyridine-4-yl) acridine is 1:1-4:1;
the solvent is a mixture of N, N-dimethylformamide and acetonitrile.
2. A cuprous iodide cluster-based coordination polymer having photothermal properties obtained by the processing method of claim 1, characterized in that: comprisingα-CuI-DPA、β-CuI-DPA andγ-at least one of CuI-DPA;
α-CuI-DPA has the formula C 92 H 60 Cu 4 I 4 N 12 Monoclinic system with space group ofP2 1 /nUnit cell parametersa、b、c8.3613 (3) A, 8.0390 (3) A, 28.8292 (11) A, respectively,α、β、γ90 DEG, 94.162 (2) DEG, 90 DEG respectively,Z=1；
β-CuI-DPA has the formula C 23 H 15 Cu 2 I 2 N 3 ·C 3 H 7 NO, monoclinic system, space groupP2 1 /cUnit cell parametersa、b、c13.5613 (12) a, 19.2762 (17) a, 10.1201 (9) a, respectively,α、β、γ90 DEG, 101.918 (3) DEG, 90 DEG respectively,Z=4；
γ-CuI-DPA has the formula C 99.39 H 66 Cu 12 I 4.61 N 19.39 O 3 Triclinic system with space group ofPUnit cell parametersa、b、c9.3687 (6) a, 13.5498 (8) a, 18.5065 (13) a, respectively,α、β、γ83.599 (2) °, 75.059 (2) °, 87.748 (2) °, respectively,Z=1。
3. the cuprous iodide-based coordination polymer with photothermal properties according to claim 2, wherein:
the molar ratio of the CuI to the 2, 7-di (pyridine-4-yl) acridine is 1:1, and the cuprous iodide cluster-based coordination polymer isα-CuI-DPA；
The molar ratio of the CuI to the 2, 7-di (pyridine-4-yl) acridine is 2:1, and the cuprous iodide cluster-based coordination polymer isβ-CuI-DPA；
The molar ratio of the CuI to the 2, 7-di (pyridine-4-yl) acridine is 4:1, and the cuprous iodide cluster-based coordination polymer isγ-CuI-DPA。
4. Use of a cuprous iodide cluster-based coordination polymer having photothermal properties as claimed in claim 2 or 3 in photothermal imaging.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210432107.8A CN114671855B (en) | 2022-04-22 | 2022-04-22 | Acridine ligand for photo-thermal material, cuprous iodide cluster-based coordination polymer with photo-thermal property, and preparation method and application thereof |
| NL2032292A NL2032292B1 (en) | 2022-04-22 | 2022-06-27 | An Iodinated Cuprous Cluster-Based Coordination Polymer as An Acridine Ligand for Photothermal Materials and with Photothermal Properties and Its Preparation Method and Application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210432107.8A CN114671855B (en) | 2022-04-22 | 2022-04-22 | Acridine ligand for photo-thermal material, cuprous iodide cluster-based coordination polymer with photo-thermal property, and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114671855A CN114671855A (en) | 2022-06-28 |
| CN114671855B true CN114671855B (en) | 2024-01-23 |
Family
ID=82080981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210432107.8A Active CN114671855B (en) | 2022-04-22 | 2022-04-22 | Acridine ligand for photo-thermal material, cuprous iodide cluster-based coordination polymer with photo-thermal property, and preparation method and application thereof |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN114671855B (en) |
| NL (1) | NL2032292B1 (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4037036A (en) * | 1974-05-24 | 1977-07-19 | Hitachi, Ltd. | 9-(P-Vinylphenyl)-acridine polymers |
| JP2003098657A (en) * | 2001-09-21 | 2003-04-04 | Fuji Photo Film Co Ltd | Positive-working original plate for printing plate |
| CN104650032A (en) * | 2015-01-23 | 2015-05-27 | 北京鼎材科技有限公司 | Acridine derivatives, and preparation method and application thereof |
| KR20170057729A (en) * | 2015-11-17 | 2017-05-25 | 주식회사 엘지화학 | Nitrile based compound and organic light emitting device comprising the same |
| CN112225751A (en) * | 2020-10-20 | 2021-01-15 | 湖北大学 | Multi-core CuI-based supramolecular cluster compound, synthesis method and application |
| CN113512050A (en) * | 2021-04-30 | 2021-10-19 | 中国计量大学 | Cuprous iodide complex-based pyridine VOC (volatile organic Compounds) fluorescent sensing material |
-
2022
- 2022-04-22 CN CN202210432107.8A patent/CN114671855B/en active Active
- 2022-06-27 NL NL2032292A patent/NL2032292B1/en active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4037036A (en) * | 1974-05-24 | 1977-07-19 | Hitachi, Ltd. | 9-(P-Vinylphenyl)-acridine polymers |
| JP2003098657A (en) * | 2001-09-21 | 2003-04-04 | Fuji Photo Film Co Ltd | Positive-working original plate for printing plate |
| CN104650032A (en) * | 2015-01-23 | 2015-05-27 | 北京鼎材科技有限公司 | Acridine derivatives, and preparation method and application thereof |
| KR20170057729A (en) * | 2015-11-17 | 2017-05-25 | 주식회사 엘지화학 | Nitrile based compound and organic light emitting device comprising the same |
| CN112225751A (en) * | 2020-10-20 | 2021-01-15 | 湖北大学 | Multi-core CuI-based supramolecular cluster compound, synthesis method and application |
| CN113512050A (en) * | 2021-04-30 | 2021-10-19 | 中国计量大学 | Cuprous iodide complex-based pyridine VOC (volatile organic Compounds) fluorescent sensing material |
Non-Patent Citations (4)
| Title |
|---|
| Ali Awada等."New Acridine-Based Tridentate Ligand for Ruthenium(II):Coordination with a Twist".《Inorganic Chemistry》.2018,第57卷(第24期),第15430-15437页. * |
| Dai, Qiuzi等."A One-step Synthesized Acridine-based Fluorescent Chemosensor for Selective Detection of Copper (II) Ions and Living Cell Imaging".《New Journal of Chemistry》.第42卷(第1期),第613-618页. * |
| Eberhard, Jens等."Synthesis and Properties of Acridine and Acridinium Dye Functionalized Bis(terpyridine) Ruthenium(II) Complexes.《European Journal of Organic Chemistry》.2018,第2018卷(第20期),第2682-2700页. * |
| Fan, Hong-Chuan等."Various Dimensional CuI-DPA Coordination Polymers Based on the Same Components for Different Electronic and Photothermal Properties".《Small Structures》.2022,第3卷(第7期),第1-11页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| NL2032292A (en) | 2022-10-06 |
| CN114671855A (en) | 2022-06-28 |
| NL2032292B1 (en) | 2023-02-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wang et al. | Preparation of two new polyimide bond linked porous covalent organic frameworks and their fluorescence sensing application for sensitive and selective determination of Fe 3+ | |
| Cheng et al. | Polymeric Cd (Se-2-NC5H4) 2 and square planar Hg (Se-2-NC5H4) 2: Volatile CVD precursors to II-VI semiconductors | |
| Xie et al. | AIE-active metal–organic frameworks: facile preparation, tunable light emission, ultrasensitive sensing of copper (ii) and visual fluorescence detection of glucose | |
| CN111253586B (en) | Cadmium-based metal-organic framework material and preparation method and application thereof | |
| Chen et al. | Luminescent homodinuclear copper (I) halide complexes based on the 3, 5-bis {6-(2, 2′-dipyridyl)} pyrazole ligand | |
| CN109054039B (en) | Synthesis and application of porous covalent organic framework material with imine structure | |
| Wang et al. | Fluorescent metal–organic frameworks based on mixed organic ligands: New candidates for highly sensitive detection of TNP | |
| Su et al. | Enhancing the photothermal conversion of tetrathiafulvalene-based MOFs by redox doping and plasmon resonance | |
| Liu et al. | Auxiliary ligand-controlled supramolecular assembly of three Cd (ii) coordination polymers based on a (E)-3-(quinolin-4-yl) acrylic acid: syntheses, structures and photoluminescent properties | |
| CN112480050B (en) | Synthesis method of fullerene spiro-derivative | |
| He et al. | The synthesis of 2-and 2, 7-functionalized pyrene derivatives through Ru (II)-catalyzed C–H activation | |
| CN113372394A (en) | Double-core host-guest supramolecule and preparation method and application thereof | |
| Zheng et al. | A new strategy for the fabrication of covalent organic framework-metal-organic framework hybrids via in-situ functionalization of ligands for improved hydrogen evolution reaction activity | |
| Lee et al. | A Ball-Joint-Type Host–Guest system that consists of conglomerate helical metallacyclophanes | |
| Guo et al. | Three layer-structured cadmium coordination polymers based on flexible 5-(4-pyridyl)-methoxylisophthalic acid: rapid synthesis and luminescence sensing | |
| Li et al. | Alkali metal-modified crystalline carbon nitride for photocatalytic nitrogen fixation | |
| CN114671855B (en) | Acridine ligand for photo-thermal material, cuprous iodide cluster-based coordination polymer with photo-thermal property, and preparation method and application thereof | |
| Zou et al. | Selective Construction of Borromean Rings and Tweezer‐Like Molecular Assembly Featuring Cp* Rh/Ir Clips for Near‐Infrared Photothermal Conversion | |
| Sun et al. | Mixed-solvothermal synthesis, structures, surface photovoltage, luminescence and molecular recognition properties of three new transition metal phosphonates with 3D framework and supramolecular structures | |
| Haitao et al. | The study on single crystal structure of [Zn (Hpdc) 2 (H2O) 2]· 2H2O (Hpdc−= 2, 5-pyridinedicarboxylic acid group) | |
| CN115028854B (en) | Semiconductor metal-organic crystal nanotube array and preparation method and application thereof | |
| Yao et al. | Construction of eight mixed-valence pentanuclear Cu I4 Cu II clusters using ligands with inhomogeneous electron density distribution: synthesis, characterization and photothermal properties | |
| Liu et al. | Target design and synthesis of three naphthyl-functionalized Copper (II) coordination compounds for their photothermal properties | |
| Jin et al. | Synthesis and crystal structure of a polymeric complex [S4Cd17 (SPh) 24 (CH3OCS2) 4/2] n· nCH3OH | |
| Qu et al. | A series of transition metal–organic frameworks: crystal structures, luminescence properties, and sensitizing for luminescent Ln (iii) ions in aqueous solution |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |