CN104892646B - High-temperature solvent thermal synthesis based on picoline-triazole Ag (I) coordination compound and application - Google Patents
High-temperature solvent thermal synthesis based on picoline-triazole Ag (I) coordination compound and application Download PDFInfo
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- CN104892646B CN104892646B CN201510203304.2A CN201510203304A CN104892646B CN 104892646 B CN104892646 B CN 104892646B CN 201510203304 A CN201510203304 A CN 201510203304A CN 104892646 B CN104892646 B CN 104892646B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic System without C-Metal linkages
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
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Abstract
The invention discloses based on picoline triazole Ag (I) coordination compound and high-temperature nuclei method thereof and application.The present invention there is two dimensional surface frame structure triazole Ag () coordination compound is mainly used in ion exchange material aspect.43 (5 picoline) 1,2,4 triazole ligand has no that document is reported, this be first case triazole Ag based on 43 (5 picoline) 1,2,4 triazole ligand () coordination compound, result of the test shows: this triazole Ag () BF in coordination compound4 ‑Anion can be exchanged by nitrate ion, this triazole Ag (
Description
About subsidizing research or the statement of exploitation: the present invention is in Tianjin application foundation and cutting edge technology research plan sky
Jinshi City's Nsfc Projects (Grant no. 14JCQNJC05900) and project of national nature science fund project (Grant
No. 21301128) carry out under subsidy.
Technical field
The invention belongs to organic synthesis and Organometallic Chemistry technical field, relate to having no picoline that document reports-
The synthesis of triazole and there is the AgBF of fluorescence property4180 DEG C of high-temperature nuclei of-L coordination compound, are based on 4-3-in particular
Triazole Ag of (5-picoline)-1,2,4-triazole ligand (L) () fluorescence complex synthesis and at ion exchange material
The application of aspect.
Background technology
Ion exchange is reversible equivalent exchange reaction.Ion during soil absorption ammonium salt has been found that as far back as 1850
Exchange phenomenon, but ion exchange is as a kind of modern separation means, is at the synthetic amberlite forties in 20th century
The thing that fat is later.The process of exchange operations and equipment, essentially identical with absorption, but the selectivity of ion exchange is higher, more
It is applicable to highly purified separation and purification.At present, ion exchange is mainly used in water process (softening and purification)；Solution (such as sugar liquid)
Refined and decolouring；Uranium and rare metal is extracted from leaching of ores liquid；Antibiotic is extracted and from Industry Waste from fermentation liquid
Water reclaims noble metal etc..
In recent years, Metal-organic complex because of it possess Stability Analysis of Structures, specific surface area is big, duct volume big and from
The fluorescent characteristic of body, has a wide range of applications, frequently as luminous material at aspects such as illumination, display, object sensing and optical devices
Expecting to apply such as light emitting diode (LEDs), the fluorescent characteristic research of coordination compound becomes a focus of MOFs research.Many
Well known, the character of any material depends primarily on their structure.How the coordination compound of controlled syntheses expected structure always with
It is all a challenging job.The luminescent properties of functional complexes is not only relevant with material composition, and very great Cheng
The molecular structure of coordination compound and intramolecular accumulation mode is depended on, so controlling the three of coordination compound on a molecular scale on degree
The accumulation mode of dimension structure and coordination compound is the most extremely important.
Solvent-thermal process refer to temperature be 100～1000 DEG C, pressure be to utilize ethanol/DMF under the conditions of 1MPa～1GPa
The synthesis carried out Deng material chemical reaction in different solutions.Under the conditions of subcritical solvent-thermal process, owing to reaction is in point
Sub-level, reactive raising, thus solvent thermal reaction can substitute some high temperature solid state reaction.Equal due to solvent thermal reaction again
Phase nucleation and nonhomogen-ous nucleation mechanism are different from the flooding mechanism of solid state reaction, thus can create other method and cannot prepare
Noval chemical compound and new material.Its advantage: product purity high, good dispersion, granularity are easy to control.
The invention belongs to organic synthesis and Organometallic Chemistry technical field, relate to that there is the three of two dimensional surface frame structure
Azoles Ag () solvent-thermal process of coordination compound, it is 4-3-(5-picoline)-1 in particular, triazole Ag of 2,4-triazole ligand
() coordination compound solvent-thermal process and as ion exchange material apply.4-3-(5-picoline)-1,2,4-triazole ligand
Having no that document is reported, this is first case based on 4-3-(5-picoline)-1, triazole Ag (I) coordination compound of 2,4-triazole ligand,
Result of the test shows: this triazole Ag (I) coordination compound has good ion-exchange performance, particularly ion exchange material aspect
There is a wide application prospect.No matter this triazole Ag (I) coordination compound is developed to the development of advanced material or to microphysics
The theoretical research learned all has great importance.
Summary of the invention
One object of the present invention discloses { [Ag (L)] (BF4)(H2O) } (1) compound.
Another object of the present invention discloses the preparation method of (1) compound crystal, the research of measurement data.
Further object of the present invention disclose have two dimensional surface frame structure triazole Ag () preparation of coordination compound.
Further object of the present invention discloses { [Ag (L)] (BF4)(H2O) } (1) compound has two dimensional surface frame structure
Coordination compound be mainly used in ion exchange material aspect.
For achieving the above object, the present invention provides following technical scheme:
Based on picoline-triazole Ag (I) coordination compound, this compound is new, does not has document by scifinder inquiry
Report this material；Its chemical general formula is as follows:
{[Ag(L)](BF4)(H2O)} ( 1)；
L structural formula is
L refers to 4-3-(5-picoline)-1,2,4-triazole ligand.
The present invention further discloses have ion exchange application triazole Ag () complex monocrystal, monoclinic crystal therein
System's BRUKER SMART 1000 X-ray single crystal diffractometer, uses the Mo of graphite monochromatorKα radiates (λ=0.071 073
Nm) as diffraction light sources, at a temperature of 173 (2) K, withScan mode, measures predominant crystal data as follows:
The present invention further discloses based on picoline-triazole Ag (I) match crystal preparation, its feature exists
In: weigh 0.0637 g (0.5 mmol) AgBF4With 5 mL water dissolutioies, weigh ligand L 0.106 g(0.5 mmol) use 5mL
Ethanol dissolves, and is simultaneously introduced ascorbic acid 0.005 g；Both the above solution is mixed, is then put in the solvent thermal still of 15 mL
Keep three days at 180 DEG C, after slow cooling, obtain colourless transparent crystal.
The present invention further discloses based on picoline-triazole Ag (I) coordination compound { [Ag (L)] (BF4)(H2O) in }
BF4 -Anion can be exchanged by nitrate ion, this triazole Ag () coordination compound has good ion-exchange performance, special
It not that molecular based ion exchange material aspect has a wide application prospect.
Accompanying drawing illustrates:
Fig. 1 be triazole Ag () molecular structure of coordination compound；
Fig. 2 be by experimental powder sample ions exchange before powder diagram (on) and ion exchange after powder diffraction
Figure (under) contrast unanimously, show that in ion exchange process, coordination compound frame structure is constant.
Detailed description of the invention
For purposes of simplicity and clarity, the most appropriate description eliminating known technology, in order to avoid those are unnecessary
The details impact description to the technical program.Below in conjunction with preferred embodiment, the present invention will be further described, the most in addition
Illustrate, prepare the initial substance AgBF of the compounds of this invention4, 5-methyl-3-aminopyridine, double formylhydrazine, DMF, ethanol
Can commercially or easily by known method prepare and (prepare the reagent used in the compounds of this invention all to come
Coming from commercially available, rank is analytical pure).
Additionally need and be illustrated: all of experimental implementation uses Schlenk technology, and solvent is pure through normal process
Change.All is all analytical pure for synthesis and the reagent analyzed, and does not process through further.Fusing point passes through Boetius
Block apparatus measures.1H H NMR spectroscopy passes through hydrargyrum variable V x300 spectrophotometer record, surveying range: 300 MHz.Chemical shift, δ,
TMS mensuration with reference to international standard.
Embodiment 1
Reference example 1 has no that the L structural formula that document is reported is
L refers to 4-3-(5-picoline)-1,2,4-triazole ligand, does not has ligand L by scifinder inquiry
Document is reported.
Preparation method: the 5-methyl-3-aminopyridine of 2.2 g, with double formylhydrazines mixing of 4.0 g, is heated to 165oC,
React 30 minutes at 185-190 DEG C, after benzene and ethanol recrystallization respectively, obtained the ligand L of white needles.Preparation literary composition
Offer: J. Org. Chem. 1953,18,1368.
Preparation embodiment 1
180 DEG C of high-temperature nuclei of coordination compound (1)
Weigh 0.0637 g (0.5 mmol) AgBF4Dissolve with 5 mLDMF, weigh ligand L 0.106 g(0.5 mmol)
Dissolve with 5mL ethanol, be simultaneously introduced ascorbic acid 0.005 g；Both the above solution is mixed, is then put into the solvent of 15 mL
Hot still keeps three days at 180 DEG C, after slow cooling, obtains colourless transparent crystal.
Elementary analysis result, experiment value (%): C, 26.67 %; H, 2.76%; N, 15.58%;
According to C16H18Ag2B2F8N8The theoretical value (%) that O calculates: C, 26.41 %; H, 2.4931%; N, 15.39%.
FT-IR (KBr, cm-1): 3400 (br), 3100 (m), 1650 (m), 1525 (m), 1380 (m),
1310 (m), 1260 (m), 1100 (br), 930 (m), 800 (m),700(m), 630 (s), 530 (m)；
Embodiment 2
(1) structure determination of coordination compound
Choose monocrystalline BRUKER SMART 1000 X-ray that size is 0.14 mm × 0.10, mm × 0.13 mm
Single crystal diffractometer, uses the Mo of graphite monochromatorKα radiation (λ=0.071 073 nm) is as diffraction light sources, at 173 (2) K
At a temperature of, withScan mode, 2.74 °≤θ≤ 29.16 ° (-10≤h≤ 10 ,-10≤k≤ 10 ,-14
≤ l≤ 13), in the range of, 4262 point diffractions, wherein 2645 independent point diffractions are collected altogether.Crystal structure
Being solved by direct method, non-hydrogen atom is obtained by difference Fourier synthetic method, and determining and revising the method for hydrogen atom is that theory adds
Hydrogen, is respectively adopted isotropism to hydrogen atom and non-hydrogen atom and anisotropy thermal parameter carries out complete matrix least square to structure
Method correction, all calculating SHELXS-97 and SHELXL-97 program bag complete.The predominant crystal data of coordination compound are listed in table
1。
No. CCDC (numbering for cambridge structure database for No. CCDC) of coordination compound 1: 1059660
The monocrystalline data of table 1 coordination compound 1
2 results and discussion
2.1 infrared spectrum
The IR of coordination compound 1 composes at 3100 cm-1There is a moderate strength absworption peak at place, and its width reaches 50 cm-1Above, return
Because of the stretching vibration of CH in the pyridine in molecule and triazole ring, owing to the association of hydrogen bond makes peak broaden.Coordination compound 1
Infrared spectrum is at 1100 cm-1The absworption peak of left and right can be designated as BF4 -The vibration peak of ion, and at 630 cm-1Indicate three
The existence of azoles cyclic group, coordination compound { [Ag (L)] (BF4)(H2O) } the infrared spectrum analysis of (1) and its crystal structure analysis result
Unanimously.
2.2 crystal structure
The crystal of coordination compound 1 belongs to monoclinic system, C2/c space group, and main bond distance and bond angle are listed in table 2, its crystal structure
As shown in Figure 1.As seen from Figure 1, each complex molecule occurs in that the structure (Ag1) of a center silver, it should be noted that
Part is presented in bridging is coordinated, and hydrone ion is present in the lattice of coordination compound 1 with end group coordination mode.For joining
The basic structural unit of compound 1, Ag1 defines four-coordination AgN with three nitrogen-atoms from three ligand moleculars respectively3Coordination
Configuration.Ag() the coordination bond lengths scope of ion and nitrogen-atoms is 0. 2197 (7) nm ~ 0. 2.409 (7) nm, these all accord with
Close bond distance's scope of document report.
Water of coordination in coordination compound, the nitrogen-atoms in ligand L and BF4-Anion defines mutually abundant C-
H N and O-H F hydrogen bond.Effect just because of these hydrogen bonds so that the steric configuration of coordination compound presents surely
Fixed Magnetic Properties of Three-Dimensional Supramolecular Complex structure.The plane that in molecule, two Pyridine Molecules and triazole molecule are formed is parallel to each other, shows altogether
Stronger pi-pi accumulation effect is there is between pyridine and the triazole plane gripped.These pi-pi accumulation effects and weak interaction enter
One step assembles coordination compound and defines the structure of Magnetic Properties of Three-Dimensional Supramolecular Complex.Result of the test shows: this triazole Ag () BF in coordination compound4 -Cloudy
Ion can be exchanged by nitrate ion, as in figure 2 it is shown, by experimental powder sample ions exchange before powder diagram (on)
With ion exchange after powder diagram (under) contrast consistent, show that in ion exchange process, coordination compound frame structure is constant, and
BF in infrared spectrum4 -Characteristic infrared peak disappear, occur in that nitrate ion characteristic infrared peak (1390 cm-1), this triazole Ag
() coordination compound has good ion-exchange performance, particularly ion exchange material aspect a wide application prospect.Should
Triazole Ag () advanced material is developed by coordination compound development or the theoretical research to microphysics all has important
Meaning.
The part bond distance of table 2 coordination compound 1 and bond angle
Embodiment 3
Metal complex concrete instance in terms of ion exchange material
Scientist exchanges by carrying out metal ion or ion in anionic complex, special to the fluorescence of coordination compound
Property artificially adjusts, and provides alternatively possible method for ion detection.Lu et al. reports group of the lanthanides coordination compound K5
[Tb5(IDC)4(ox)4] (IDC=imidazole-4,5-dicarboxylic acid, ox=oxalate), wherein guest ions K+Can be with various
Cation carries out ion exchange.Tb3+Ion from5D4Track transits to7F5The emissive porwer of track is at Ca2+Have notable after addition
Increase.Work as Ca2+When the amount added is original 3 times, fluorescence retention time rises to 287.48 μ s from 158.90 μ s.Other
Cation such as Na+, NH4 +, Mg2+, Sr2+, Ba2+, Zn2+, Cd2+, Hg2+And Pb2+Fluorescence intensity, transition gold can not be affected
Belong to Mn2+, Fe2+, Co2+, Ni2+And Cu2+Fluorescence intensity can be weakened.The reason producing sensor mechanism is Ca2+And OX2-Between deposit
In strong interaction so that OX2-More rigidity, thus reduce OX2-The inactivation that vibration causes, increases from part to Tb3+ energy jumps
Move efficiency.List of references: W. G. Lu, L. Jiang, X. L. Feng and T. B. Lu,Inorg. Chem.,
48, 6997(2009).
Embodiment 4
Triazole Ag based on 4-3-(5-picoline)-1,2,4-triazole ligand () coordination compound is as ion exchange material
Application.
Method: Bio-Rad FTS 135 infrared spectrometer produced by BIO-RAD company of the U.S., (real to this compound
Execute example 1) carry out the scanning of infrared spectrum, by Rigaku D/max2500 powder diffractometer, to this compound (embodiment 1)
Carry out the sign of powder diffraction.
Conclusion: this coordination compound is at 1100 cm-1The absworption peak of left and right can be designated as BF4 -The vibration peak of ion.
Step: under room temperature condition by triazole Ag of 4-3-(5-picoline)-1,2,4-triazole ligand () complex monocrystal
Sample is immersed in NaNO3Methanol solution (saturated concentration) in, owing to coordination compound is insoluble in methanol, it is solid to suspend in the solution
Body exists.After soaking five days, solid suspension is filtered, repeatedly wash with methanol, then raw by BIO-RAD company of the U.S.
Bio-Rad FTS 135 infrared spectrometer produced, the coordination compound sample after exchanging ion carries out the scanning of infrared spectrum, simultaneously
Coordination compound sample after exchanging ion carries out the sign of powder diffraction.
Conclusion: BF in the sample infrared spectrum after ion exchange4 -Characteristic infrared peak disappear, occur in that nitrate ion is special
Levy infrared peak (1390 cm-1), and by experimental powder sample ions exchange before powder diagram (on) and ion exchange after
Powder diagram (under) contrast unanimously, show that in ion exchange process, coordination compound frame structure is constant, this triazole Ag () coordinate
BF in thing4 -Can be exchanged by nitrate ion, simultaneously the stablizing of holding frame shelf structure.
Conclusion:
The invention discloses triazole Ag based on 4-3-(5-picoline)-1,2,4-triazole ligand () coordination compound and
180 DEG C of high-temperature solvent process for thermosynthesizing and application.The present invention there is two dimensional surface frame structure triazole Ag () coordinate owner
Ion exchange material aspect to be applied to.4-3-(5-picoline)-1,2,4-triazole ligand have no that document is reported, this is first
Example triazole Ag based on 4-3-(5-picoline)-1,2,4-triazole ligand () coordination compound, result of the test shows: this triazole Ag
() BF in coordination compound4 -Anion can be exchanged by nitrate ion, this triazole Ag () coordination compound has good ion
Switching performance, number particularly ion exchange material aspect has a wide application prospect.This triazole Ag () coordination compound development
Advanced material is developed or the theoretical research to microphysics all has great importance.
Claims (4)
1. monocrystalline based on picoline-triazole Ag (I) coordination compound, it is characterised in that crystallographic system BRUKER of this monocrystalline
SMART 1000 X-ray single crystal diffractometer, uses the Mo of graphite monochromatorKα radiates, and λ=0.071 073 nm are as diffraction
Light source, at a temperature of 172 (2) K, withScan mode, measures predominant crystal data as follows:
Described based on picoline-triazole Ag (I) complex monocrystal, its chemical formula is as follows:
[Ag(L)](BF4)(H2O), L structural formula is
L refers to 4-3-(5-picoline)-1,2,4-triazole ligand.
2. preparation method based on picoline-triazole Ag (I) complex monocrystal described in a claim 1, it is characterised in that:
Weigh 0.0637 g AgBF4Dissolve with 5 mLDMF, weigh ligand L 0.106 g 5mL ethanol and dissolve, be simultaneously introduced Vitamin C
Acid 0.005 g；Both the above solution is mixed, is then put in the solvent thermal still of 15 mL under 180 ° of C and keeps three days, slowly
Colourless transparent crystal is obtained after cooling；
L refers to 4-3-(5-picoline)-1,2,4-triazole ligand.
3. based on the application in terms of ion exchange material of picoline-triazole Ag (I) complex monocrystal described in claim 1.
4. the application described in claim 3, wherein said ion exchange material refers to: hand at gas storage, separation, ion
Change the application in field.
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