CN108129674A - Leucine Schiff class silver complex fluorescent crystal material and preparation method thereof - Google Patents
Leucine Schiff class silver complex fluorescent crystal material and preparation method thereof Download PDFInfo
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- CN108129674A CN108129674A CN201711434698.8A CN201711434698A CN108129674A CN 108129674 A CN108129674 A CN 108129674A CN 201711434698 A CN201711434698 A CN 201711434698A CN 108129674 A CN108129674 A CN 108129674A
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Abstract
The invention discloses a kind of leucine Schiff class silver complex fluorescent crystal materials and its preparation method and application, and step is：Into the mixed solution of the ethyl alcohol containing N (4 picolyl) L leucine reduced form Schiff anion ligands and water, second acid for adjusting pH value is added in, solvent is removed and obtains ligand HLOAc, then by the silver salt of metering and ligand HLOAcThe in the mixed solvent of ethyl alcohol and water is dissolved in, a period of time is stood after being completely dissolved, filtering, obtained colorless cleared solution, it is allowed to volatilize naturally at room temperature, clear crystal is obtained within two weeks or so, it is collected by filtration, then it is washed with ethyl alcohol, it is dry, you can to obtain the fluorescent crystal material.The present invention has synthesized two kinds of N (4 picolyl) L leucine reduced form Schiff silver complexes using room temperature volatility process, required equipment is simple in this reaction, it is easy to operate feasible, it is reproducible, the complex of gained has many advantages, such as that fluorescence, yield are high, easy to carry, is expected to be used widely in terms of fluorescent material.
Description
Technical field
The present invention relates to transition-metal coordination technical field of polymer, relate in particular to a kind of N- (4- picolyls)-
L- leucine reduced forms Schiff silver (I) complex and preparation method thereof.
Background technology
Schiff has multiple oxygen and nitrogen-atoms, is a kind of important organic ligand, synthesizes relatively easy, Er Qieneng
The reactants such as a variety of different amino acid and the different aldehydes or ketones with carbonyl is neatly selected to be reacted, therefore it is being coordinated
Chemical developer process plays an important role, and Schiff has been widely used as multi-functional cheland, and contains transition gold
The Schiff base complex of category has also been widely studied (Moradi-Shoeili Z, Amini Z, Boghaei D M, et al.
Polyhedron,2013,53:76-82.Ozaki Y,Kawashima T,Abeyoshizumi R,et
al.Biochemistry, 2014,53(38):6032-40.).But from structure, Schiff ligand has stronger
Schiff reduction in order to overcome this weakness, enhances its flexibility, and its coordination site and its coordination mode are more by rigidity
It is versatile and flexible.
And such reduced form Schiff coordinate complex has successfully synthesized in recent years, and they in light, magnetism, urge
The fields such as change show potential application prospect (Liu Y Y, Gong W J, Ma J C, et al.Journal of
Coordination Chemistry,2013,66(22):4032-4051.Zhang Z H,Yang X S,Zhang Q Q,et
al.Rsc Advances, 2016,6(106).).And correlation d10The complex report of the reduction Schiff of metallic silver is more rare
See, simultaneously [AgL2]ClO4(4) and [AgL2]BF4(5) (L=2- (the chloro- 8- quinoline oxies of 5-) -1- (pyrrolidin-1-yl) second
Ketone) two kinds of silver complexes are used as fluorescent material (the Chinese Journal of Inorganic Chemistries such as Lin Long, Li Xianhong, wave, 2016,32 (9):
The Chinese Journal of Inorganic Chemistries such as 1653-1658. Ma Yan, Bi Kailun, Cui Yangzhe, 2016,32 (5):884-890.).
Invention content
The purpose of the present invention is the silver (I) of open one kind N- (4- picolyls)-L-Leu reduced form Schiff is matched
Close object fluorescent crystal material and preparation method, the material fluorescence is good and preparation method simple possible, and yield height is reproducible, just
In carrying.
Realizing the object of the invention technical solution is：
Heretofore described leucine Schiff class silver complex fluorescent crystal material, chemical formula are： [Ag3
(LOAc)2NO3]n(1) or [Ag (LOAc)(H2O)2]n(2), wherein, LOAc=N- (4- picolyls)-L-Leu reduced form
Schiff anion ligand, the molecular formula of the ligand are as follows：
。
Further, the complex [Ag of the reduced form Schiff of above structure3(LOAc)2NO3]n(complex 1), belongs to
Monoclinic system, space group C2, cell parameter are：A=7.3225 (12), b=8.0975 (13),α=
90 °, β=95.460 (4) °, γ=90 ° contain the silver atoms there are two types of coordination configuration in basic coordination structure.
Further, the complex [Ag of the reduced form Schiff of above structure3(LOAc)2NO3]nIn (complex 1)
Containing there are two types of the silver atoms of coordination configuration, respectively three-fold coordination and four-coordination, bridging is used as by ligand and forms one-dimentional structure
Coordination polymer.
Further, the complex [Ag (L of the reduced form Schiff of above structureOAc)(H2O)2]n(complex 2) belongs to
In rhombic system, space group P212121, cell parameter is：A=5.6807 (10), b=13.443 (2),α=90 °, β=90 °, γ=90 °, basic coordination structure contain the silver atoms there are one crystallography independence.
Further, the complex [Ag (L of the reduced form Schiff of above structureOAc)(H2O)2]nIn (complex 2)
Containing there are one silver atoms (Ag1), wherein, Ag1 is four-coordination, and is used as bridging by ligand and forms one-dimentional structure, silver ion with
N in ligand, N, O coordinations.
The preparation method of the leucine Schiff class silver complex fluorescent crystal material of above structure, as steps described below
It carries out：
Mixing to ethyl alcohol and water containing N- (4- picolyls)-L-Leu reduced form Schiff anion ligand
In solution, second acid for adjusting pH value is added in, solvent is removed and obtains ligand HLOAc, then by the silver salt of metering and ligand HLOAcIt is dissolved in second
The in the mixed solvent of alcohol and water stands a period of time after being completely dissolved, filtering, obtained colorless cleared solution allows it in room temperature
It is lower to volatilize naturally, it obtains clear crystal within two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, it is dry, you can to obtain described
Fluorescent crystal material.
Further, second acid for adjusting pH value is added in 4~6.
Further, ethyl alcohol containing N- (4- picolyls)-L-Leu reduced form Schiff anion ligand with
In the mixed solution of water, the volume ratio of ethyl alcohol and water is 1:1.
Further, by the silver salt of metering and ligand HLOAcThe in the mixed solvent of ethyl alcohol and water is dissolved in, wherein, ethyl alcohol and water
Volume ratio be 2:1~1:2.
Further, silver salt in the soluble-salts such as silver nitrate, silver perchlorate, silver fluoride any one or a few.
Further, when silver salt and ligand HLOAcThe ratio between the amount of substance be 2:1~3:When 2, complex 1 is obtained.
Further, when silver salt and ligand HLOAcThe ratio between the amount of substance be 1:1~1:When 2, complex 2 is obtained.
Since silver-colored (I) complex has fluorescence, by leucine Schiff class silver complex fluorescence of the present invention
Crystalline material is expected to be applied in terms of fluorescent material as fluorescent crystal material.
Compared with prior art, the present invention has synthesized two kinds of N- (4- picolyls)-L-Leu using room temperature volatility process
Reduced form Schiff silver (I) complex, required equipment is simple in this reaction, easy to operate feasible, reproducible, the cooperation of gained
Object has many advantages, such as that fluorescence, yield are high, easy to carry, is expected to be used widely in terms of fluorescent material.
Description of the drawings
Fig. 1 is matched containing silver-colored (I) in silver-colored (I) complex 1 of N- (4- picolyls)-L-Leu reduced form Schiff
Position environment map.
Fig. 2 is matched containing silver-colored (I) in silver-colored (I) complex 2 of N- (4- picolyls)-L-Leu reduced form Schiff
Position environment map.
Fig. 3 is that the solid containing silver-colored (I) complex 1 and 2 of N- (4- picolyls)-L-Leu reduced form Schiff is glimmering
Light spectrogram.
Specific embodiment
(1)HLOAcThe structure of ligand：
(2)HLOAcThe synthesis of ligand：
Mixing to ethyl alcohol and water containing N- (4- picolyls)-L-Leu reduced form Schiff anion ligand
In solution, second acid for adjusting pH is added in 4-6, filtrate is rotated into removing solvent after filtering and obtains white solid, then it is dissolved in heat
Filtrate revolving can obtain ligand HL by methanol again except desaltingOAc。
(3) synthesis of N- (4- picolyls)-L-Leu reduced form Schiff silver-colored (I) and characterization
Embodiment 1：
2mmol N- (4- picolyls)-L-Leu reduced form Schiff ligand HLOAc(608mg) is dissolved in 5mL water,
1mmol silver nitrates (169mg) are dissolved in 5mL ethyl alcohol.After two solution are mixed, a period of time is stood, filtrate is sealed and pricked by filtering
Hole obtains clear crystal in two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, obtains complex 1, spontaneously dries, yield
It is 67%.
Embodiment 2：
1.5mmol N- (4- picolyls)-L-Leu reduced form Schiff ligand HLOAc(456mg) is dissolved in 5mL
Water, 1mmol silver nitrates (169mg) are dissolved in 5mL ethyl alcohol.After two solution are mixed, a period of time is stood, filtering is close by filtrate
Feng Zhakong obtains clear crystal in two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, obtains complex 1, spontaneously dries,
Yield is 65%.
Embodiment 3：
2mmol N- (4- picolyls)-L-Leu reduced form Schiff ligand HLOAc(608mg) is dissolved in 10mL
Water, 1mmol silver nitrates (169mg) are dissolved in 5mL ethyl alcohol.After two solution are mixed, a period of time is stood, filtering is close by filtrate
Feng Zhakong obtains clear crystal in two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, obtains complex 1, spontaneously dries,
It spontaneously dries, yield 66%.
Embodiment 4：
1.5mmol N- (4- picolyls)-L-Leu reduced form Schiff ligand HLOAc(456mg) is dissolved in 5mL
Water, 1mmol silver nitrates (169mg) are dissolved in 10mL ethyl alcohol.After two solution are mixed, a period of time is stood, filtering is close by filtrate
Feng Zhakong obtains clear crystal in two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, obtains complex 1, spontaneously dries,
Yield is 63%.
Embodiment 5：
1.5mmol N- (4- picolyls)-L-Leu reduced form Schiff ligand HLOAc(456mg) is dissolved in 10mL
Water, 1mmol silver nitrates (169mg) are dissolved in 5mL ethyl alcohol.After two solution are mixed, a period of time is stood, filtering is close by filtrate
Feng Zhakong obtains clear crystal in two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, obtains complex 1, spontaneously dries,
Yield is 61%.
Embodiment 6：
1mmol N- (4- picolyls)-L-Leu reduced form Schiff ligand HLOAc(304mg) is dissolved in 5mL water,
1mmol silver nitrates (169mg) are dissolved in 5mL ethyl alcohol, after two solution are mixed, stand a period of time, natural filtration is close by filtrate
Feng Zhakong obtains clear crystal in two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, obtains complex 2, spontaneously dries,
Yield is 62%.
Embodiment 7：
1mmol N- (4- picolyls)-L-Leu reduced form Schiff ligand HLOAc(304mg) is dissolved in 5mL water,
2mmol silver nitrates (338mg) are dissolved in 5mL ethyl alcohol, after two solution are mixed, stand a period of time, natural filtration is close by filtrate
Feng Zhakong obtains clear crystal in two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, obtains complex 2, spontaneously dries,
Yield is 66%.
Embodiment 8：
1mmol N- (4- picolyls)-L-Leu reduced form Schiff ligand HLOAc(304mg) is dissolved in 5mL water,
1mmol silver nitrates (169mg) are dissolved in 10mL ethyl alcohol, after two solution are mixed, stand a period of time, natural filtration, by filtrate
Hole is pricked in sealing, obtains clear crystal within two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, obtain complex 2, naturally dry
It is dry, yield 64%.
Embodiment 9：
1mmol N- (4- picolyls)-L-Leu reduced form Schiff ligand HLOAc(304mg) is dissolved in 10mL
Water, 1mmol silver nitrates (169mg) are dissolved in 5mL ethyl alcohol, after two solution are mixed, stand a period of time, natural filtration will be filtered
Liquid-tight Feng Zhakong obtains clear crystal in two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, obtains complex 2, natural
It is dry, yield 60%.
Embodiment 10：
1mmol N- (4- picolyls)-L-Leu reduced form Schiff ligand HLOAc(304mg) is dissolved in 5mL water,
2mmol silver nitrates (338mg) are dissolved in 10mL ethyl alcohol, after two solution are mixed, stand a period of time, natural filtration, by filtrate
Hole is pricked in sealing, obtains clear crystal within two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, obtain complex 2, naturally dry
It is dry, yield 45%.
Embodiment 11：
1mmol N- (4- picolyls)-L-Leu reduced form Schiff ligand HLOAc(304mg) is dissolved in 10mL
Water, 2mmol silver nitrates (338mg) are dissolved in 5mL ethyl alcohol, after two solution are mixed, stand a period of time, natural filtration will be filtered
Liquid-tight Feng Zhakong obtains clear crystal in two weeks or so, it is collected by filtration, is then washed with ethyl alcohol, obtains complex 2, natural
It is dry, yield 51%.
Embodiment 12：
(1) crystal structure determination
Crystal structure determination uses Bruker Apex II CCD diffractometers, under 296 (2) K, with through graphite monochromatised
Mo K alpha raysPoint diffraction is collected with ω scan modes, the data of collection are used in combination by SAINT programe reductions
SADABS methods carry out semiempirical absorption correction.Structure elucidation and refine be respectively adopted SHELXTL programs SHELXS and
SHELXL is completed, by complete matrix least square method to F2It is modified to obtain the coordinate and anisotropy of whole non-hydrogen atoms
Parameter.All hydrogen atoms are fixed on by theory on parent during structure refinement, assign parent displacement parameter 1.2 or
The isotropism displacement parameter of 1.5 times (C-H, 1.2 or O/N-H, 1.5 times).Detailed axonometry data are shown in Table 1.Silver cooperation
The coordination environment graph structure of object is shown in attached drawing 1 and Fig. 2.
(2) solid fluorescence performance test
Powdered complex sample is enriched with, again passes by further grinding, carries out solid fluorescence test：Complex exists
It is excited at 350nm, maximum emission peak is obtained at 361nm and 426nm, therefore, the reduced form Schiff Ag (I) is matched
Solvate crystal, to have stronger fluorescent effect at 361nm and 426nm two, is shown in Fig. 3 (instrument models in launch wavelength：Varian
Cary Eclipse spectrometer)。
Above example is merely to illustrate present disclosure, and in addition to this, the present invention also has other embodiment.It is but all
The technical solution formed using equivalent replacement or equivalent deformation mode is all fallen in protection scope of the present invention.
The predominant crystal data of 1 complex 1 of table and complex 2
aR=Σ | | Fo|-|Fc||/Σ|Fo|.
bRw=[Σ [w (Fo 2-Fc 2)2]/Σw(Fo 2)2]1/2.
cGOF={ Σ [w (Fo 2-Fc 2)2]/(n-p)}1/2.。
Claims (10)
1. leucine Schiff class silver complex fluorescent crystal material, which is characterized in that its chemical formula is：[Ag3(LOAc)2NO3]n(1) or [Ag (LOAc)(H2O)2]n(2), wherein, LOAc=N- (4- picolyls)-L-Leu reduced form Schiff
Anion ligand, the molecular formula of the ligand are as follows：
2. fluorescent crystal material as described in claim 1, which is characterized in that [Ag3(LOAc)2NO3]n(1) belong to monoclinic system,
Space group is C2, and cell parameter is：A=7.3225 (12), b=8.0975 (13), α=90 °, β=
95.460 (4) °, γ=90 ° contain the silver atoms there are two types of coordination configuration in basic coordination structure, pass through ligand LOAcAs bridge
Connection forms the coordination polymer of one-dimentional structure.
3. fluorescent crystal material as described in claim 1, which is characterized in that [Ag (LOAc)(H2O)2]n(2) belong to orthorhombic
System, space group P212121, cell parameter is：A=5.6807 (10), b=13.443 (2), α=90 °, β
=90 °, γ=90 °, basic coordination structure contains the silver atoms there are one crystallography independence, and passes through ligand LOAcAs bridging
Form the coordination polymer of one-dimentional structure.
4. the preparation method of leucine Schiff class silver complex fluorescent crystal material, it is characterised in that：
To containing N- (4- picolyls)-ethyl alcohol of L-Leu reduced form Schiff anion ligand and the mixed solution of water
In, second acid for adjusting pH value is added in, solvent is removed and obtains ligand HLOAc, then by the silver salt of metering and ligand HLOAcBe dissolved in ethyl alcohol with
The in the mixed solvent of water, after being completely dissolved stand a period of time, filtering, obtained colorless cleared solution, allow its at room temperature from
So volatilization until obtaining clear crystal, it is collected by filtration, is then washed with ethyl alcohol, dry, you can it is brilliant to obtain the fluorescence
Body material.
5. preparation method as claimed in claim 4, which is characterized in that contain N- (4- picolyls)-L-Leu reduced form
In the ethyl alcohol of Schiff anion ligand and the mixed solution of water, the volume ratio of ethyl alcohol and water is 1:1.
6. preparation method as claimed in claim 4, which is characterized in that by the silver salt of metering and ligand HLOAcIt is dissolved in ethyl alcohol and water
In the mixed solvent, wherein, the volume ratio of ethyl alcohol and water is 2:1~1:2.
7. preparation method as claimed in claim 4, which is characterized in that it is solvable that silver salt is selected from silver nitrate, silver perchlorate, silver fluoride
Any one or a few in property salt.
8. preparation method as claimed in claim 4, which is characterized in that when silver salt and ligand HLOAcThe ratio between the amount of substance be 2:
1~3:When 2, complex 1 is obtained.
9. preparation method as claimed in claim 4, which is characterized in that when silver salt and ligand HLOAcThe ratio between the amount of substance be 1:
1~1:When 2, complex 2 is obtained.
10. crystalline material as described in claim 1 is in the purposes as fluorescent material.
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Citations (4)
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| US20080153121A1 (en) * | 2006-02-28 | 2008-06-26 | University Of Washington | Chemical Sensor Enhanced by Direct Coupling of Redox Enzyme to Conductive Surface |
| CN103765215A (en) * | 2011-06-07 | 2014-04-30 | 生命科技公司 | Fluorogenic semiconductor nanocrystals |
| CN104761575A (en) * | 2015-03-19 | 2015-07-08 | 金华职业技术学院 | Eugenol nicotinicate-silver (I) complex, and preparation method and use thereof |
| CN107325117A (en) * | 2017-07-07 | 2017-11-07 | 常州大学 | Structure of chiral silver complex of N pyridines threonine derivatives and preparation method thereof |
-
2017
- 2017-12-26 CN CN201711434698.8A patent/CN108129674A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080153121A1 (en) * | 2006-02-28 | 2008-06-26 | University Of Washington | Chemical Sensor Enhanced by Direct Coupling of Redox Enzyme to Conductive Surface |
| CN103765215A (en) * | 2011-06-07 | 2014-04-30 | 生命科技公司 | Fluorogenic semiconductor nanocrystals |
| CN104761575A (en) * | 2015-03-19 | 2015-07-08 | 金华职业技术学院 | Eugenol nicotinicate-silver (I) complex, and preparation method and use thereof |
| CN107325117A (en) * | 2017-07-07 | 2017-11-07 | 常州大学 | Structure of chiral silver complex of N pyridines threonine derivatives and preparation method thereof |
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Application publication date: 20180608 |