CN104610371B - A kind of metal iridium complex and its application - Google Patents
A kind of metal iridium complex and its application Download PDFInfo
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- CN104610371B CN104610371B CN201510038667.5A CN201510038667A CN104610371B CN 104610371 B CN104610371 B CN 104610371B CN 201510038667 A CN201510038667 A CN 201510038667A CN 104610371 B CN104610371 B CN 104610371B
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- 239000002184 metal Substances 0.000 title claims abstract description 22
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 22
- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 21
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 21
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000007689 inspection Methods 0.000 claims 1
- 150000002500 ions Chemical class 0.000 abstract description 14
- 238000001514 detection method Methods 0.000 abstract description 13
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 238000012544 monitoring process Methods 0.000 abstract description 4
- 238000004020 luminiscence type Methods 0.000 abstract description 2
- 238000011084 recovery Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 11
- 239000010949 copper Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000031700 light absorption Effects 0.000 description 6
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000004847 absorption spectroscopy Methods 0.000 description 3
- 229910001431 copper ion Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- -1 2- pyridine radicals Chemical class 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 150000005837 radical ions Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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"
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The invention discloses a kind of metal iridium complex and its application, the structural formula of the metal iridium complex is：Or, it has good luminescent properties in visible region, and luminescent lifetime is long.Ni metal2+Ion can react with the metal iridium complex, it is set to produce luminescence queenching, and when there is the cyanide ion of various concentrations in system, the luminescent properties of metal iridium complex can be made to obtain different degrees of recovery, so as to reach the purpose to cyanide ion qualitative and quantitative detection, the environmental monitoring to cyanide is significant.
Description
Technical field
The invention belongs to chemical material and environmental monitoring technology field, and in particular to a kind of metal iridium complex and its in cyanogen
Application in radical ion detection.
Background technology
Cyanide is widely used in the industrial productions such as gold mining, plating, metallurgy, and plastics shaping processing, curriery, stone
In the different neck material such as change, photography, steel, nylon, but its leakage and discharge inevitably cause pole to the mankind and environment
Big harm.The mankind can touch cyanide by multiple channels such as food, industry, surrounding environment, and cyanide can be by exhaling
Desorption system, digestive system, or even skin enter human body, so as to influence the different physiological roles of human body, such as angiocarpy, vision, in
The normal operation of pivot nerve, internal system etc..Extensive use and its hypertoxic feature for having due to cyanide, in recent years,
How to develop a kind of high selectivity, highly sensitive probe, scientific research personnel has been caused to carry out qualitative and quantitative detection to cyanide
Great interest, and the cyanide ion detection agent for being currently based on metal complex is also rarely reported.Therefore, find a kind of to cyanogen root
There is ion high selectivity and highly sensitive metal complex to have very important significance.
The content of the invention
It is an object of the invention to provide a kind of metal iridium complex and its application, the metal iridium complex is in system
Cyanide ion has high selectivity and high sensitivity, can be used for the detection of cyanide ion content in environment.
To achieve the above object, the present invention is adopted the following technical scheme that：
A kind of metal iridium complex, its structural formula is：
（Ⅰ）Or（Ⅱ）.
The metal iridium complex can be used for the detection of cyanide ion, and this is due to not being coordinated with metal iridium in complex
Two nitrogen-atoms as electron donor, nitrogen-atoms in the ability with complexation of metal ions, such as complex can complex copper ion,
Make complex that luminescence queenching to occur, but cyanide ion is more stronger than copper ion with the complexing power of nitrogen-atoms in complex, therefore,
In system add cyanide ion after, it is replaceable go out copper ion, the luminous of complex is restored, so as to reach detection cyanogen root from
The purpose of son.
Remarkable advantage of the invention is：Metal iridium complex of the present invention has that sensitivity is high, stoke shift is big, luminous
Long lifespan, the preferable feature of phosphorescence performance, and be difficult by ambient interferences, the detection to cyanide ion qualitative, quantitative is capable of achieving, it is right
The environmental monitoring of cyanide is significant.
Brief description of the drawings
Fig. 1 is metal iridium complex and various concentrations Cu2+The ultraviolet-visible absorption spectroscopy figure of ionic reaction, wherein（A）For
Complex（Ⅰ）,（B）It is complex（Ⅱ）.
Fig. 2 is metal iridium complex-Cu and various concentrations CN-The ultraviolet-visible absorption spectroscopy figure of ionic reaction, wherein
（A）It is complex（Ⅰ）,（B）It is complex（Ⅱ）.
Fig. 3 is metal iridium complex and various concentrations Cu2+The luminescent spectrum figure of ionic reaction, wherein（A）It is complex
（Ⅰ）,（B）It is complex（Ⅱ）.
Fig. 4 is metal iridium complex-Cu and various concentrations CN-The luminescent spectrum figure of ionic reaction, wherein（A）It is complex
（Ⅰ）,（B）It is complex（Ⅱ）.
Specific embodiment
In order that content of the present invention easily facilitates understanding, with reference to specific embodiment to of the present invention
Technical scheme is described further, but the present invention is not limited only to this.
Embodiment 1
Complex（Ⅰ）Synthesis step it is as follows：
Under nitrogen protection, by 25 mg [(ppy)2IrCl]2It is molten with 10 mg 2,3- bis- (2- pyridine radicals) pyrazine (bppz)
In dichloromethane and methyl alcohol by volume 1：In the solvent of 1 mixing, it is heated to reflux under condition of nitrogen gas 12 hours, is cooled to room temperature,
Then remove solvent under reduced pressure, purified using chromatographic column（With CH2Cl2：MeOH=40：1 is eluent system）, obtain orange-red solid
Body, yield is about 80%：
ESI-MS under positive ion mode（CH2Cl2）：m/z=735；H-NMR（400 MHz）δ：8.73（D,J=2.6Hz, 1H）,
8.58（D,J=3.8Hz, 1H）, 8.40（D,J=7.6Hz, 1H）, 8.14（D,J=4.8Hz, 1H）, 8.09（D,J=6.7Hz, 1H）,
8.02（D,J=2.6Hz, 1H）, 7.99（D,J=4.7Hz, 1H）, 7.93（T,J=7.7Hz, 3H）, 7.82（Dd,J=16.8Hz,
8.4Hz, 3H）, 7.71（Dd,J=7.1Hz, 4.5Hz, 2H）, 7.54（Dd,J=7.5Hz, 4.8Hz, 1H）, 7.42（Dd,J=
14.3Hz, 7.3Hz, 2H）, 7.22（T,J=6.2Hz, 2H）, 7.07（Td,J=7.4Hz, 3.3Hz, 2H）, 6.95（Dt,J=
10.7Hz, 7.0Hz, 2H）, 6.33（D,J=7.5Hz, 1H）, 6.27（D,J=7.4Hz, 1H）.
Embodiment 2
Complex（Ⅱ）Synthesis step it is as follows：
Under nitrogen protection, by 25 mg [(ppy)2IrCl]2With 10 mg 4,7-phenanthrolino-5,6:5',
6'-pyraz-ine（ppz）Part is dissolved in dichloromethane and methyl alcohol by volume 1：In the solvent of 1 mixing, heated under condition of nitrogen gas
Backflow 12 hours, is cooled to room temperature, then removes solvent under reduced pressure, is purified using chromatographic column（With CH2Cl2：MeOH=40：1 is wash-out
System）, orange-red solid is obtained, yield is about 80%：
ESI-MS under positive ion mode（CH2Cl2）：m/z=733；H-NMR（400 MHz）δ：9.57（1 H, d,J=
8.4Hz）, 9.50（1 H, d,J=8.6Hz）, 9.33（2 H, d,J=3.5Hz）, 8.49-8.42（2 H, m）, 8.19（2 H, dd,J
=8.3Hz, 4.0Hz）, 8.16-8.08（2 H, m）, 7.92（2 H, d,J=7.8Hz）, 7.86（2 H, t,J=6.3Hz）, 7.69（1
H, d,J=6.0Hz）, 7.57（1 H, d,J=5.7Hz）, 7.13（2 H, t,J=7.6Hz）, 7.00（2 H, t,J=7.3Hz）, 6.95
（2 H, s）, 6.41（2 H, dd,J=16Hz）.
Embodiment 3
（1）It is 1.0 × 10 in concentration-5The complex of mol/L（Ⅰ）Or complex（Ⅱ）Acetonitrile solution in, be separately added into
A series of different amounts of Cu2+Ion, and its ultraviolet-visible absorption spectroscopy in 200-800 nm wave-length coverages is determined respectively, tie
Fruit sees Fig. 1.Such as Fig. 1（A）It is shown, complex（Ⅰ）Light absorption value at 240nm and 380nm wavelength with Cu2+The increasing of ion concentration
Greatly（0 → 3.0 times）And increase；Such as Fig. 1（B）It is shown, complex（Ⅱ）Light absorption value at 250nm and 450nm wavelength with Cu2+
The increase of ion concentration（0 → 1.0 times）And increase, with Cu at 310nm wavelength2+The increase of ion concentration and reduce.
（2）It is 1.0 × 10 in concentration-5The complex of mol/L（Ⅰ）- Cu or complex（Ⅱ）In the acetonitrile solution of-Cu, point
A series of different amounts of CN are not added-Ion, and its ultravioletvisible absorption in 200-800 nm wave-length coverages is determined respectively
Spectrum, is as a result shown in Fig. 2.Such as Fig. 2（A）It is shown, complex（Ⅰ）The light absorption value of-Cu is at 250nm and 400nm wavelength with CN-From
The increase of sub- concentration（0 → 2.7 times）And increase, with CN at 330nm wavelength-The increase of ion concentration and reduce, work as addition
CN-Concentration is 7.84 × 10-6~2.55×10-5When in the range of mol/L, its light absorption value and CN-Ion concentration is linear,
Detection is limited to 4.74 × 10-6mol/L；Such as Fig. 2（B）It is shown, complex（Ⅱ）The light absorption value of-Cu at 410nm wavelength with
CN-The increase of concentration（0 → 2.5 times）And reduce, the CN of addition-Ion concentration is 3.99 × 10-7-2.08×10-5Mol/L models
When enclosing interior, its light absorption value and CN-Ion concentration is linear, and detection is limited to 3.15 × 10-7 mol/L。
（3）It is 3.0 × 10 in concentration-5The complex of mol/L（Ⅰ）Or complex（Ⅱ）Acetonitrile solution in, be separately added into
A series of different amounts of Cu2+Ion, and its luminescent spectrum in 400-800 nm wave-length coverages is determined respectively, as a result see Fig. 3.
Such as Fig. 3（A）It is shown, complex（Ⅰ）Luminous intensity at 654nm wavelength with Cu2+The increase of ion concentration（0 → 2.0 times）
And reduce；Such as Fig. 3（B）It is shown, complex（Ⅱ）Luminous intensity at 670nm wavelength with Cu2+The increase of ion concentration（0
→ 1.0 times）And reduce.
（4）It is 3.0 × 10 in concentration-5The complex of mol/L（Ⅰ）- Cu or complex（Ⅱ）In the acetonitrile solution of-Cu, point
A series of different amounts of CN are not added-Ion, and its luminescent spectrum in 400-800 nm wave-length coverages is determined respectively, as a result
See Fig. 4.Such as Fig. 4（A）It is shown, complex（Ⅰ）The luminous intensity of-Cu is at 654nm wavelength with CN-The increase of ion concentration（0
→ 2.2 times）And increase, as the CN for adding-Ion concentration is 9.53 × 10-6-3.13×10-5When in the range of mol/L, it lights
Intensity and CN-Ion concentration is linear, and detection is limited to 5.90 × 10-6mol/L；Such as Fig. 4（B）It is shown, complex（Ⅱ）-
The luminous intensity of Cu is at 670nm wavelength with CN-The increase of ion concentration（0 → 2.0 times）And increase, as the CN for adding-Ion
Concentration is 1.20 × 10-7-3.87×10-5In the range of mol/L, its luminous intensity and CN-Ion concentration is linear, detection
It is limited to 1.2 × 10-7 mol/L。
Metal iridium complex of the present invention is good to cyanide ion selectance, sensitivity is high and is difficult, by ambient interferences, to be capable of achieving
Detection to cyanide ion qualitative, quantitative, the environmental monitoring to cyanide is significant.
The foregoing is only presently preferred embodiments of the present invention, all impartial changes done according to scope of the present invention patent with
Modification, should all belong to covering scope of the invention.
Claims (2)
1. a kind of metal iridium complex, it is characterised in that：The structural formula of the metal iridium complex is：
Or。
2. a kind of application of metal iridium complex as claimed in claim 1, it is characterised in that：Use it for the inspection of cyanide ion
Survey.
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| CN201510038667.5A CN104610371B (en) | 2015-01-27 | 2015-01-27 | A kind of metal iridium complex and its application |
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| CN201510038667.5A CN104610371B (en) | 2015-01-27 | 2015-01-27 | A kind of metal iridium complex and its application |
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| CN104610371B true CN104610371B (en) | 2017-07-04 |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103555321A (en) * | 2013-10-30 | 2014-02-05 | 南京邮电大学 | Phosphorescent ionic type iridium complex probe and preparation method and application thereof |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103555321A (en) * | 2013-10-30 | 2014-02-05 | 南京邮电大学 | Phosphorescent ionic type iridium complex probe and preparation method and application thereof |
Non-Patent Citations (4)
| Title |
|---|
| A Bis(ferrocenyl)phenanthroline Iridium(III) Complex as a Lab-on-a-Molecule for Cyanide and Fluoride in Aqueous Solution;Qinghai Shu等,;《Inorg. Chem.》;20121126;13123-13127 * |
| A CN- specific turn-on phosphorescent probe with probable application for enzymatic assay and as an imaging reagent;Upendar Reddy G.等,;《Chem. Commun.》;20121031;255-257 * |
| Multisignaling detection of cyanide anions based on an iridium(III) complex: remarkable enhancement of sensitivity by coordination effect;Bin Lou等,;《New Journal of Chemistry》;20091120;132-136 * |
| Photodynamic Behavior of Heteroleptic Ir(III) Complexes with Carbazole-Functionalized Dendrons Associated with Efficient Electron Transfer Processes;Ah-Reum Hwang等,;《J. Phys. Chem. C》;20111208;1973-1986 * |
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