CN105713027B - A kind of benzimidizole derivatives cadmium complex and its preparation method and application - Google Patents
A kind of benzimidizole derivatives cadmium complex and its preparation method and application Download PDFInfo
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- CN105713027B CN105713027B CN201610040478.6A CN201610040478A CN105713027B CN 105713027 B CN105713027 B CN 105713027B CN 201610040478 A CN201610040478 A CN 201610040478A CN 105713027 B CN105713027 B CN 105713027B
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- 229910052793 cadmium Inorganic materials 0.000 title claims abstract description 24
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000013078 crystal Substances 0.000 claims abstract description 13
- 238000001914 filtration Methods 0.000 claims abstract description 7
- OKIIEJOIXGHUKX-UHFFFAOYSA-L Cadmium iodide Inorganic materials [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 4
- WLZRMCYVCSSEQC-UHFFFAOYSA-N cadmium(2+) Chemical compound [Cd+2] WLZRMCYVCSSEQC-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 9
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- -1 iodide ions Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000001455 metallic ions Chemical class 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
- 238000001338 self-assembly Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
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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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
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- 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
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- 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
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention relates to cadmium complex, more particularly to a kind of benzimidizole derivatives cadmium complex, particularly a kind of cadmium complex with fluorescence property constructed based on cadmium (II) ion and 1 (1 (4 pyridylmethyl) 1H benzimidazolyl-2 radicals-yl) ethanol and its preparation method and application.The chemical formula of benzimidizole derivatives cadmium complex of the present invention is：[Cd(HPyBIE)I2]n, HPyBIE represents 1 (1 (4 pyridylmethyl) 1H benzimidazolyl-2 radicals-yl) ethanol in formula.The preparation method of benzimidizole derivatives cadmium complex of the present invention, comprises the following steps：(1) it is 1 by mol ratio:1 HPyBIE parts and CdI2It is dissolved separately in ethanol, the two is mixed；(2) stir at room temperature, solution is placed in reactor, be put in baking oven, 120 DEG C of constant temperature reacts 72 hours, is down to room temperature with 5 10 DEG C/h speed, yellow bulk crystals to be had separate out, and filtering, collection is made.The present invention has preparation method technique simple, and crystal prototype purity is high, and growth is fast, the advantages of high income.
Description
Technical field
The present invention relates to cadmium complex, and in particular to a kind of benzimidizole derivatives cadmium complex, particularly one kind are based on
The cadmium with fluorescence property that cadmium (II) ion and 1- (1- (4- pyridylmethyls) -1H- benzimidazolyl-2 radicals-yl) ethanol are constructed
Complex and its preparation method and application.
Background technology
Transient metal complex is due to multifrequency natures such as light, electricity, magnetic, in field tables such as catalysis, luminous, biological medicines
Reveal wide application prospect.Benzimidazole and its derivative are a kind of with stronger coordination ability, flexible and changeable coordination mode
Organic bridge ligand, can with metal ion carry out self assembly obtain the complex of a variety of novel structures.Benzimidazole derivatess
The complex that thing is constructed suffers from being widely applied in fields such as catalysis, magnetic, fluorescence, nonlinear opticses.1- (1- (4- pyridines
Ylmethyl) -1H- benzimidazolyl-2 radicals-yl) ethanol, itself has good luminescent properties, particularly when its with d10Electronics
After the metallic ion coordination of structure forms complex, there is very high application value in terms of fluorescence property.
The content of the invention
It is an object of the invention to provide a kind of benzimidizole derivatives cadmium complex and its preparation method and application.
The chemical formula of benzimidizole derivatives cadmium complex of the present invention is：[Cd(HPyBIE)I2]n, HPyBIE is represented in formula
1- (1- (4- pyridylmethyls) -1H- benzimidazolyl-2 radicals-yl) ethanol, n repeateding unit numbers.
The crystal of the complex belongs to monoclinic system, space group P21/c, cell parameter： α=γ=90 °, β=122.305
(4)°.The complex is one-dimensional catenary structure, cadmium ion comprising a four-coordination in an asymmetric cell, two coordinations
Iodide ion, a HPyBIE part.Central metal Cd (II) ion uses four-coordination pattern [CdN2I2], respectively with one
Benzimidazole N Atomic coordinates on HPyBIE partsIt is former with the pyridine N on another HPyBIE part
Son coordinationWith two free iodide ions coordinations, Cd-I bond distance be 2.7127 (7) and
In complex, part HPyBIE is formed with two tooth overseas Chinese federation patterns and Cd (II) ion coordination along c directions connection Cd (II) ion
The distance between one-dimensional catenary structure, CdCd isAdjacent one-dimensional molecular is connected by O-HI
Into two-dimensional structure, two-dimensional mesh is connected by hydrogen bond, finally constitutes tridimensional network.Complex and respective ligand under room temperature condition
Solid fluorescence emission spectrum show that the fluorescence emission peak of part is located at 364nm and 445nm (λex=315nm), its fluorescence comes
From π * → π or π * → n charge transtion.Complex [Cd (HPyBIE) I2]nFluorescence emission peak be 390 and 515nm (λex=
314nm), close with part HPyBIE peak position, the fluorescence peak comes from the charge transtion with internal π * → π.
Complex of the present invention is through elementary analysis C15H15CdI2N3O(619.50):Theoretical value：C,29.08,H,2.44,N,
6.78. experiment value:C, 29.15, H, 2.46, N, 6.86%. IR Characterizations (KBr, ν/cm-1):3734w,3383s,2979m,
2932w,1620s,1495w,1474m,1456w,1429s,1361w,1327m,1273w,1220w,1164w,1109w,
1071w,1040w,1022w,994w,910w,842w,800w,775w,759w,746m,583w,573w,513w,470w.
The preparation method of benzimidizole derivatives cadmium complex of the present invention, comprises the following steps：
(1) it is 1 by mol ratio:1 HPyBIE parts and CdI2It is dissolved separately in ethanol, the two is mixed；
(2) stirring at room temperature, solution is placed in reactor, be put in baking oven, 120 DEG C of constant temperature reacts 72 hours,
Room temperature is down to 5-10 DEG C/h speed, yellow bulk crystals to be had separate out, and filtering, collection is made.
The benzimidizole derivatives cadmium complex of the present invention may be used as fluorescent optics material.
Benzimidizole derivatives cadmium complex of the present invention is obtained with solvent-thermal method, and preparation method technique is simple,
Crystal prototype purity is high, and growth is fast, high income.Benzimidizole derivatives cadmium complex provided by the invention is to be based on benzimidazole
What derivative ligand was constructed, the solid fluorescence emission spectrum of complex is shown under room temperature condition, when excitation wavelength is 314nm,
Complex can launch wavelength be 515nm green glow.
Brief description of the drawings
Fig. 1 is benzimidizole derivatives cadmium complex structure chart prepared by the embodiment of the present invention 1；
Fig. 2 is the solid state fluorescence of benzimidizole derivatives cadmium complex prepared by the embodiment of the present invention 1 and part in 298K
Spectrogram.
Embodiment
Embodiment 1
By 2mLCdI2The ethanol solution of (0.1mmol) is added in the ethanol solution of 2mL HPyBIE parts (0.1mmol),
The mixed solution is put into reactor again, is placed in baking oven, 120 degrees Celsius are reacted 72 hours after constant temperature, with 5 DEG C/h speed
Room temperature is down to, has the precipitation of yellow bulk crystals, filtering, collects product, yield：65%.
The structure determination of benzimidizole derivatives cadmium complex：
Crystal structure determination uses Bruker type X-ray single crystal diffractometers, is penetrated using by graphite monochromatised Mo-K α
Line For incident radiation, withScan mode collects point diffraction, and crystalline substance is obtained by least square refinement
Born of the same parents' parameter, crystal structure is solved from difference Fourier electron-density map using SHELXL-97 direct methods, and through Lorentz and pole
Change effect amendment.Detailed axonometry data are shown in Table 1.Structure is shown in Fig. 1.
The crystallographic data of the complex of table 1
The luminosity of benzimidizole derivatives cadmium complex：
We determine the Solid fluorescene spectrum (Fig. 2) of ligands and complexes at room temperature.The fluorescent emission peak position of part
In 364nm and 445nm (λex=315nm), charge transtion of its fluorescence from π * → π or π * → n.Complex [Cd
(HPyBIE)I2]nFluorescence emission peak be 390 and 515nm (λex=314nm), close with part HPyBIE peak position, this is glimmering
Photopeak comes from the charge transtion with internal π * → π.
Embodiment 2
The ethanol solution of 2mL HPyBIE parts (0.1mmol) is added into 2mLCdI2In the ethanol solution of (0.1mmol),
The mixed solution is put into reactor again, is placed in baking oven, 120 degrees Celsius are reacted 70 hours after constant temperature, with 5 DEG C/h speed
Room temperature is down to, has the precipitation of yellow bulk crystals, filtering, collects product, yield：62%.
Its structure determination and structural formula are same as Example 1.
Embodiment 3
By 2mLCdI2The ethanol solution of (0.1mmol) is added in the ethanol solution of 2mL HPyBIE parts (0.1mmol),
The mixed solution is put into reactor again, is placed in baking oven, 120 degrees Celsius are reacted 72 hours after constant temperature, with 10 DEG C/h speed
Degree is down to room temperature, has the precipitation of yellow bulk crystals, filtering, collects product, yield：63%.
Its structure determination and structural formula are same as Example 1.
Embodiment 4
The ethanol solution of 2mL HPyBIE parts (0.1mmol) is added into 2mLCdI2In the ethanol solution of (0.1mmol),
The mixed solution is put into reactor again, is placed in baking oven, 120 degrees Celsius are reacted 70 hours after constant temperature, with 10 DEG C/h speed
Degree is down to room temperature, has the precipitation of yellow bulk crystals, filtering, collects product, yield：64%.
Its structure determination and structural formula are same as Example 1.
Claims (3)
- A kind of 1. benzimidizole derivatives cadmium complex, it is characterised in that：The chemistry of the benzimidizole derivatives cadmium complex Formula is：[Cd(HPyBIE)I2]n, HPyBIE represents 1- (1- (4- pyridylmethyls) -1H- benzimidazolyl-2 radicals-yl) second in formula Alcohol, n repeateding unit numbers, the crystal of the complex belong to monoclinic system, space group P21/c, cell parameter： α=γ=90 °, β=122.305 (4) °.
- 2. the preparation method of benzimidizole derivatives cadmium complex described in claim 1, it is characterised in that comprise the following steps：(1) it is 1 by mol ratio:1 HPyBIE parts and CdI2It is dissolved separately in ethanol, the two is mixed；(2) stir at room temperature, solution is placed in reactor, be put in baking oven, 120 DEG C of constant temperature reacts 72 hours, with 5- 10 DEG C/h speed is down to room temperature, and yellow bulk crystals to be had separate out, and filtering, collection is made.
- 3. the application of benzimidizole derivatives cadmium complex described in claim 1, it is characterised in that as fluorescent optics material.
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