CN110467631A - A kind of copper (I) alkynes cluster with aggregation-induced emission and circular polarised luminescence - Google Patents
A kind of copper (I) alkynes cluster with aggregation-induced emission and circular polarised luminescence Download PDFInfo
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- CN110467631A CN110467631A CN201910807631.7A CN201910807631A CN110467631A CN 110467631 A CN110467631 A CN 110467631A CN 201910807631 A CN201910807631 A CN 201910807631A CN 110467631 A CN110467631 A CN 110467631A
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- 238000004220 aggregation Methods 0.000 title abstract description 15
- 230000002776 aggregation Effects 0.000 title abstract description 15
- 238000004020 luminiscence type Methods 0.000 title abstract description 15
- -1 copper (I) alkynes Chemical class 0.000 title abstract description 7
- 239000010949 copper Substances 0.000 claims abstract description 42
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910052802 copper Inorganic materials 0.000 claims abstract description 30
- 239000000463 material Substances 0.000 claims abstract description 23
- 239000003446 ligand Substances 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 4
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 claims abstract description 3
- 239000002184 metal Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000013110 organic ligand Substances 0.000 claims description 3
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000003384 imaging method Methods 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000002086 nanomaterial Substances 0.000 abstract description 2
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000001345 alkine derivatives Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FGOSNANIQLJNSZ-UHFFFAOYSA-N acetonitrile copper Chemical compound [Cu].CC#N.CC#N.CC#N.CC#N FGOSNANIQLJNSZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001142 circular dichroism spectrum Methods 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- 238000001093 holography Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- 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
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- 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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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Abstract
The invention discloses a kind of copper (I) alkynes cluster with aggregation-induced emission and circular polarised luminescence, belongs to the crossing domain of Coordinative Chemistry and nano material.The chirality Nanometer Copper cluster enantiomer is protection ligand with chiral ligand (R/S) -2- diphenyl-hydroxymethyl pyrrolidine -1- propine (R/S-DPM), and by simple room temperature volatilization one pot process, yield is high, and luminescent properties are excellent.The chemical formula of the enantiomer cluster are as follows: C160H160P6Cu14F36O8It (writes a Chinese character in simplified form are as follows: R/S-DPM-Cu14), belong to rhombic system, space group is chiral space groupP212121.The copper nanocluster has red fluorescence at room temperature；Its chiral structure and luminescent properties assign the stronger circular polarised luminescence of the cluster (CPL) property, this has a good application prospect it in terms of luminescent material and chiral optical material；The copper nanocluster has aggregation-induced emission (AIE) property, with the increase of poor solvent content, fluorescence enhancement, and realizes strong circular polarised luminescence (CPL) property, and fluorescence dissymmetry factor is up to 1.0 × 10‑2, aggregation-induced emission property, extra small size and hypotoxicity can be used for bright cell imaging.
Description
Technical field
The invention belongs to the crossing domains of Coordinative Chemistry and nano material, and in particular to one kind have aggregation-induced emission and
Copper (I) alkynes cluster of circular polarised luminescence.
Background technique
The preparation and research of the accurate metal nanometer cluster of atom have become in nano science field one it is brand-new great
The research direction of prospect.One kind that metal nanometer cluster is usually made up of to several hundred a metallic atoms organic ligand bridging by ten
Cluster compound with accurate atomic structure.Its bridge as connection atom and nanoparticle, metal nanometre cluster show uniqueness
Light, electricity, chemical property.It is so compared with gold and silver, copper has cheap, crustal abundance height, the lot of advantages such as from a wealth of sources.So
And since the synthesis of copper cluster is difficult and easy to oxidize in air, synthesizing the copper cluster that shines is still a huge challenge, and copper cluster is ground
Study carefully the especially accurate copper of atom (I) alkynes cluster still at an early stage.
Chirality is the generally existing phenomenon of nature, in drug design, bio-identification, enantioselectivity catalysis, optics
The fields such as device, holographic technique, chiral sensing and separation have broad application prospects.The accurate nanocluster of atom is detection
The particularly preferred model of chirality origin.So realize the metal nanometer cluster with circular polarised luminescence (CPL) performance, it is chiral and strong
Strong fluorescence is its precondition.Chiral ligand induction is a kind of method that is most controllable and effectively realizing chirality first,
Secondary aggregation-induced emission (AIE) characteristic also has become a kind of a kind of promising plan for improving metal nanometer cluster quantum yield
Slightly.But the relevant report of Nanometer Copper (I) cluster of the alkynes ligand protection with CPL performance is had no at present.So design synthesis is former
Sub accurate, structure determination, the copper nanocluster with CPL performance are in the fields such as line holographic projections and imaging biological cells and diagnosis and treatment
It has a good application prospect.
Summary of the invention
Present invention aims at synthesize a kind of copper (I) alkynes cluster with aggregation-induced emission and circular polarised luminescence.
For this purpose, the present invention has developed a kind of copper (I) alkynes cluster with aggregation-induced emission and circular polarised luminescence, the chirality
The chemical formula of Nanometer Copper cluster are as follows: C160H160P6Cu14F36O8It (writes a Chinese character in simplified form are as follows: R/S-DPM-Cu14), belong to rhombic system, space group is
Chiral space group P212121,
Wherein R/S-DPM is (R/S) -2- diphenyl-hydroxymethyl pyrrolidine -1- propine, and skeleton symbol is as follows:
The preparation method of copper nanocluster material of the present invention is achieved by the steps of:
By ligand (R/S) -2- diphenyl-hydroxymethyl pyrrolidine -1- propine and four acetonitrile copper dissolution of hexafluorophosphoric acid in toluene
In acetone mixed solution, dissolution clarification is stirred at room temperature, clear solution is placed in after terminating and is protected from light volatilization at room temperature, obtains by reaction
Crystal filtering, with ethanol washing, room temperature is dried.
The copper nanocluster is the kernel being made of 14 copper atoms, and (Fig. 1 is protected by 8 organic ligands in periphery
It is shown).14 copper atoms form the cube kernel of a distortion, Cu by metal interaction14Metal framework is considered as
It is the Cu of a distortion6 6+Octahedron is encapsulated in Cu8 8+Ethynylene group in cube (shown in Fig. 2), on periphery protection ligand
Using μ3-η1,η1,η2μ2-η1,η2Coordination mode, the nitrogen-atoms on each ligand, oxygen atom and 1 copper atom are coordinated (Fig. 3 institute
Show).
Copper (I) alkynes cluster of the present invention with aggregation-induced emission and circular polarised luminescence, property are described in detail below:
The material has aggregation-induced emission performance, does not have fluorescence in dichloromethane solution, not androgynous when being added
When the poor solvent n-hexane of product number, extent of polymerization changes, fluorescence enhancement, shows as apparent solvent aggregation inducing
It can be (shown in Fig. 4).Aggregation-induced emission (AIE) triggers the circular polarised luminescence characteristic of the accurate copper of atom (I) alkynes cluster simultaneously
(CPL) (shown in Figures 5 and 6).The material crystalline state has red fluorescence at room temperature, and best launch wavelength position is
726nm (excitation wavelength 445nm) (shown in Fig. 7), the hand-type structure and fluorescence make it have very strong circular polarised luminescence characteristic
(shown in Fig. 8), fluorescence dissymmetry factor is up to 1.0 × 10-2, this is very high value in reported chiral cluster, in holography
Projection, the fields such as information storage and cell imaging have a good application prospect.
The invention has the advantages that: chiral Nanometer Copper clustered materials of the invention to have the accurate structure of atomic size, can be from original
Accurate Characterization is carried out to structure in sub- rank；The Nanometer Copper clustered materials have aggregation-induced emission property, extra small size and
Good biocompatibility, can be applied to cell imaging；Chiral Nanometer Copper clustered materials state of aggregation and crystalline state have compared with
The high chiral characteristics of luminescence has extraordinary application value.
Detailed description of the invention
Fig. 1 is a pair of of enantiomer-specific structure schematic diagram of Nanometer Copper clustered materials monocrystalline of the present invention.
Fig. 2 is the inner core schematic diagram of Nanometer Copper clustered materials monocrystalline of the present invention.
Fig. 3 is the ligands pattern diagram of Nanometer Copper clustered materials monocrystalline of the present invention.
Fig. 4 is Nanometer Copper clustered materials of the present invention in the fluorescence photo in different proportion hexane solution (under 365nm ultraviolet lamp).
Fig. 5 is circular polarised luminescence (CPL) curve graph of Nanometer Copper clustered materials of the present invention in different proportion hexane solution.
Fig. 6 is chiral circular dichroism spectra (CD) curve graph of Nanometer Copper clustered materials of the present invention in different proportion hexane solution.
Fig. 7 is the excitation curve and launching curve figure of solid nano copper clustered materials of the present invention.
Fig. 8 is circular polarised luminescence (CPL) curve graph of solid nano copper clustered materials of the present invention.
Specific embodiment
Below by example, the present invention is described further:
Embodiment 1: the synthesis of Nanometer Copper clustered materials of the present invention
By 0.035mmol (R/S) -2- diphenyl-hydroxymethyl pyrrolidine -1- propine (R/S-DPM) and 0.035mmol hexafluoro
Four acetonitrile copper dissolution of phosphoric acid in the mixed solution of 2mL toluene and 2mL acetone, after reaction will by quick agitating solution clarification
Clear solution is placed in and is protected from light volatilization at room temperature, and orange bulk crystals, yield 50%, filtering, with ethanol washing, room are obtained after 2 days
Temperature is dried for its property test material.
Nanometer Copper clustered materials of the present invention made from Example 1 further characterize, and process is as follows:
(1) crystal structure determination
The X-ray single crystal diffraction data of complex are with sizeable single crystal samples in Rigaku XtaLAB Pro single crystal diffraction
It is measured on instrument.Data are with through graphite monochromatised CuK alpha rayExisted for diffraction source by ω scanning mode
It is collected at a temperature of 200K, and passes through Lp factor correction and semiempirical absorption correction.Structure elucidation is to first pass through SHELXS-97 program
Just structure is obtained with direct method, then uses the complete matrix least square method refine of SHELXL-97 program.All non-hydrogen atoms are equal
Using anisotropic thermal parametric method refine.All hydrogen atoms all use isotropism thermal parameter method refine.Detailed crystal is surveyed
Fixed number evidence is shown in Table 1.
The predominant crystal data of the Nanometer Copper clustered materials of the present invention of table 1
1 predominant crystal data of table
R1=∑ | | Fo|-|Fc||/∑|Fo|.wR2=[∑ w (Fo 2-Fc 2)2/∑w(Fo 2)2]1/2
Above embodiments are merely to illustrate the contents of the present invention, and in addition to this, there are also other embodiments by the present invention.But it is all
It is fallen within the scope of protection of the present invention using the technical solution that equivalent replacement or equivalent deformation mode are formed.
Claims (3)
1. a kind of chirality Nanometer Copper clustered materials, it is characterised in that: its chemical formula are as follows: C160H160P6Cu14F36O8, write a Chinese character in simplified form are as follows: R/S-
DPM-Cu14, belong to rhombic system, space group is chiral space group P212121,
Wherein R/S-DPM is (R/S) -2- diphenyl-hydroxymethyl pyrrolidine -1- propine, and skeleton symbol is as follows:
2. chirality Nanometer Copper clustered materials as described in claim 1, it is characterised in that: it forms kernel by 14 copper atoms, outside
It encloses and is protected by 8 organic ligands；14 copper atoms form the cube kernel of a distortion, Cu by metal interaction14Gold
Belong to the Cu that frame is a distortion6 6+Octahedron is encapsulated in Cu8 8+In cube, the ethynylene group on periphery protection ligand is adopted
Use μ3-η1,η1,η2μ2-η1,η2Coordination mode, the nitrogen-atoms on each ligand, oxygen atom and 1 copper atom are coordinated.
3. chirality Nanometer Copper clustered materials as claimed in claim 1 or 2, it is characterised in that: its mono-crystalline structures such as attached drawing 1.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111423876A (en) * | 2020-05-08 | 2020-07-17 | 无锡市疾病预防控制中心 | Preparation method of silver-sulfur nano cluster aggregate with circular polarization luminescence |
| CN111748340A (en) * | 2020-06-29 | 2020-10-09 | 浙江师范大学 | Novel fluorescent silver nanocluster and synthesis method and application thereof |
| CN115746314A (en) * | 2022-10-11 | 2023-03-07 | 河南理工大学 | Chiral luminescent gold-silver-doped nanocluster material and synthesis method and application thereof |
| CN116063242A (en) * | 2023-02-07 | 2023-05-05 | 郑州大学 | Chiral Cu capable of emitting near infrared light 6 Cluster material and application thereof in night vision imaging |
| CN117264626A (en) * | 2023-09-20 | 2023-12-22 | 郑州大学 | Super-atom copper-silver alloy cluster with circular polarized luminescence |
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| CN110105378A (en) * | 2019-05-27 | 2019-08-09 | 华中科技大学 | A kind of copper-based circularly polarized luminescence and its preparation and application |
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| CN110105378A (en) * | 2019-05-27 | 2019-08-09 | 华中科技大学 | A kind of copper-based circularly polarized luminescence and its preparation and application |
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| JOSEPH P .BYRNE ET AL.,: ""ChiropticalProbing of Lanthanide-Directed Self-Assembly Formation Usingbtp Ligands Formed inOne-Pot Diazo-T ransfer/ Deprotection Click Reactionfrom Chiral Amines"", 《CHEM. EUR.J.》 * |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111423876A (en) * | 2020-05-08 | 2020-07-17 | 无锡市疾病预防控制中心 | Preparation method of silver-sulfur nano cluster aggregate with circular polarization luminescence |
| CN111423876B (en) * | 2020-05-08 | 2023-12-29 | 无锡市疾病预防控制中心 | Preparation method of silver-sulfur nanocluster with circularly polarized luminescence |
| CN111748340A (en) * | 2020-06-29 | 2020-10-09 | 浙江师范大学 | Novel fluorescent silver nanocluster and synthesis method and application thereof |
| CN111748340B (en) * | 2020-06-29 | 2022-11-15 | 浙江师范大学 | Fluorescent silver nanocluster and synthesis method and application thereof |
| CN115746314A (en) * | 2022-10-11 | 2023-03-07 | 河南理工大学 | Chiral luminescent gold-silver-doped nanocluster material and synthesis method and application thereof |
| CN115746314B (en) * | 2022-10-11 | 2023-08-01 | 河南理工大学 | Chiral luminescent gold-silver doped nanocluster material and synthesis method and application thereof |
| CN116063242A (en) * | 2023-02-07 | 2023-05-05 | 郑州大学 | Chiral Cu capable of emitting near infrared light 6 Cluster material and application thereof in night vision imaging |
| CN116063242B (en) * | 2023-02-07 | 2024-02-27 | 郑州大学 | Chiral Cu capable of emitting near infrared light 6 Cluster material and application thereof in night vision imaging |
| CN117264626A (en) * | 2023-09-20 | 2023-12-22 | 郑州大学 | Super-atom copper-silver alloy cluster with circular polarized luminescence |
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