CN104370949A - Chiral naphthyl diacetic acid-bis(triazolyl)zinc coordination compound and preparation method thereof - Google Patents
Chiral naphthyl diacetic acid-bis(triazolyl)zinc coordination compound and preparation method thereof Download PDFInfo
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- CN104370949A CN104370949A CN201410634399.9A CN201410634399A CN104370949A CN 104370949 A CN104370949 A CN 104370949A CN 201410634399 A CN201410634399 A CN 201410634399A CN 104370949 A CN104370949 A CN 104370949A
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- naphthyl
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- 239000011701 zinc Substances 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 title abstract description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title abstract 2
- 125000001624 naphthyl group Chemical group 0.000 title abstract 2
- 229910052725 zinc Inorganic materials 0.000 title abstract 2
- 150000003852 triazoles Chemical class 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- -1 naphthyl oxalic acid Chemical compound 0.000 claims description 7
- 235000006408 oxalic acid Nutrition 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 5
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 5
- 239000004246 zinc acetate Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 125000006850 spacer group Chemical group 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 4
- 239000002178 crystalline material Substances 0.000 abstract 1
- 238000004729 solvothermal method Methods 0.000 abstract 1
- UHIJLWIHCPPKOP-UHFFFAOYSA-N [N].[Zn] Chemical class [N].[Zn] UHIJLWIHCPPKOP-UHFFFAOYSA-N 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 239000003446 ligand Substances 0.000 description 4
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 230000003592 biomimetic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001857 fluorescence decay curve Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- 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
- C07F3/06—Zinc 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
-
- 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)
Abstract
The invention relates to a chiral naphthyl diacetic acid-bis(triazolyl)zinc coordination compound and a preparation method thereof, belonging to the technical field of chemistry. The chemical formula of the coordination compound is [Zn3(L)3(btb)(H2O)2], wherein L is deprotonated (S)-(-)-1,1'-bisnaphthyl-2,2'-diacetic acid anion, and btb is 1,6-hexyl-bis(triazole). The coordination compound is prepared by a solvothermal process. The coordination compound has high fluorescence emission intensity; and the obtained crystalline material can be further developed and applied in the field of fluorescent materials.
Description
technical field
The invention belongs to technical field of chemistry, be specifically related to a kind of transition metal complex and preparation method thereof.
Background technology
Chirality ligand polymer is widely studied due to the potential using value in molecular recognition, catalysis, optical material and biomimetic chemistry etc. (U. Knof, A. von Zelewsky,
angew. Chem. Int. Ed.
1999, 38,302; A. L ü tzen, M. Hapke, J. Griep-Raming, D. Haase, W. Saak, Angew. Chem. Int. Ed.
2002,
41, 2086).Chiral diol, as 1,1 '-diphenol and 1,1 '-bisnaphthol is often used as chiral template, construct chiral coordination compound (M. Canlica, T. Nyokong,
dalton Trans.
2011,
40, 1497; R. Wang, L. Xu, X. Li, Y. Li, Q. Shi, Z. Zhou, M. Hong, A. S. C. Chan,
eur. J. Inorg. Chem. 2004, 1595).Compared with traditional title complex, the research of chiral coordination compound is still less, especially based on chirality organic carboxyl acid and N mix neutral ligand researches (C.-D. Wu, W. Lin,
angew. Chem.
2005, 117,1994; G. Yuan, C. Zhu, Y. Liu, W. Xuan, Y. Cui, J. Am. Chem. Soc.
2009, 131,10452; Y.-H.
liu, C.-C. Peng, S.-H. Lee, P.-H. Chien, P.-C. Wu,
crystEngComm,
2013,
15, 10333; I. Mihalcea, N. Zill, V. Mereacre, C. E. Anson, A. K. Powell,
cryst.
growth Des.
2014,
14, 4729; S.-C. Chen, F. Tian, K.-L. Huang, C.-P. Li, J. Zhong, M.-Y. He, Z.-H. Zhang, H.-N. Wang, M. Du, Q. Chen,
crystEngComm 2014,
16, 7673).
We have chosen chirality 1 first, 1 '-bis--beta naphthal oxalic acid (H
2l) and two (triazole) (btb) of 1,6-hexyl be research object, based on the metal complexes research also unmanned report so far of this mixed ligand.
H
2l and btb part.
Summary of the invention
The object of the invention is the two naphthyl oxalic acid of open a kind of chirality and two (triazole) Zn complex of hexyl.
The present invention also discloses the preparation method of this chiral zinc nitrogen complexes.
The chiral zinc nitrogen complexes of two naphthyl oxalic acid has following chemical formula, that is: [Zn
3(L)
3(btb) (H
2o)
2], wherein L is (S)-(-)-1, l of deprotonation '-bis-naphthyl-2,2 '-oxalic acid anion ligand, btb is 1,6-hexyl two (triazole).
Complex crystal belongs to oblique system, spacer is C2, unit cell parameters is a=26.7280 (5), b=9.4040 (3), c=17.3890 (6), α=90 °, β=102.582 (5) °, γ=90 °, V=4265.8 (2)
3, title complex is laminate structure.
The preparation method of the chiral zinc nitrogen complexes of described two naphthyl oxalic acid, comprises the steps:
The synthesis of the chiral zinc nitrogen complexes of two naphthyl oxalic acid: get equimolar zinc acetate, H
2l and btb puts into tetrafluoroethylene reactor, is that water and the ethanol of 7:1 and 6:2 is mixed solvent with volume ratio, places in an oven, is heated to 100 DEG C of constant temperature 72 hours, then slowly drops to room temperature and obtains.
Chiral zinc nitrogen complexes preparation method of the present invention is simple, repeatability is strong, product performance are stablized.
Fluorescence data shows title complex of the present invention and has stable fluorescence property, can be applied as fluorescent material at material science.
Accompanying drawing explanation
Fig. 1 is the coordination environment figure of metal in title complex;
Fig. 2 is two-dimensional layered structure figure;
Fig. 3 is the fluorescence emission spectrogram of title complex;
Fig. 4 is the fluorescent quenching graphic representation of title complex;
Fig. 5 is the powder diagram of title complex.
Embodiment
Embodiment 1
By zinc acetate 0.05 mmol, H
2l 0.05 mmol and btb 0.05 mmol puts into 15 mL tetrafluoroethylene reactors, with 7 mL water and 1 mL ethanol for mixed solvent, places in an oven, is heated to 100 DEG C of constant temperature 72 hours, then slowly drops to room temperature, productive rate 32%.
Embodiment 2
By zinc acetate 0.05 mmol, H
2l 0.05 mmol and btb 0.05 mmol puts into 15 mL tetrafluoroethylene reactors, with 6 mL water and 2 mL ethanol for mixed solvent, places in an oven, is heated to 100 DEG C of constant temperature 72 hours, then slowly drops to room temperature, productive rate 20%.
Main infrared absorption peak is: 3276 (w), 3124 (w), 2924 (w), 1622 (s), 1507 (w), 1460 (w), 1428 (m), 1358 (w), 1279 (m), 1150 (w), 1064 (w), 996 (w), 811 (w), 746 (w), 710 (w), 607 (w), 537 (w), 440 (w).
The relevant characterization of title complex
(1) crystal structure determination of title complex
The diffraction data of title complex collects on Oxford Diffraction Gemini R Ultra diffractometer, Mo K
αray (λ=0.71069), 293 K.Operation technique scanning corrects.Crystalline structure is solved with direct method by SHELEXL-97 program, uses SHELEXL-97 to carry out refine by complete matrix method of least squares.The temperature factor anisotropy of non-hydrogen atom is revised.Detailed axonometry data are in table 1; Important bond distance and bond angle data are in table 2; Crystalline structure is shown in Fig. 1-Fig. 2.
The title complex of invention is characterized in that described complex crystal belongs to oblique system, spacer is C2/c, unit cell parameters is a=26.7280 (5), b=9.4040 (3), c=17.3890 (6), α=90 °, β=102.582 (5) °, γ=90 °, V=4265.8 (2)
3.One and half Zn (II) ion is comprised, one and half L negatively charged ion, half btb part and a coordinated water molecule in title complex unit cell.Zn1 is positioned at reversion center, is the octoploids structure of slightly distortion; Zn2 is tetrahedral configuration.Zn (II) ion is connected for laminate structure with btb part by L negatively charged ion.
(2) photoluminescent property research (FLSP920 Edinburgh fluorescence spectrophotometer) of title complex.
When 330 nm excite, title complex has the last one emission peak (Fig. 3) at 370 nm places, and carry out matching to the fluorescence decay curve of title complex, fluorescence lifetime is
τ 1=0.59 ns(87.76%) and
τ 2=2.58 ns(12.24%) (Fig. 4).
Table 1 is the predominant crystal data of title complex
| formula | C 82H 68N 6O 20Zn 3 |
| Mr | 1653.53 |
| crystal system | monoclinic |
| space group | C2 |
| a (?) | 26.7280(5) |
| b (?) | 9.4040(3) |
| c (?) | 17.3890(6) |
| α(°) | 90 |
| β(°) | 102.582(5) |
| γ(°) | 90 |
| V (? 3) | 4265.8(2) |
| Z | 2 |
| D calc (g cm -3) | 1.287 |
| F(0 0 0) | 1704 |
| R int | 0.0378 |
| GOF on F 2 | 1.090 |
| R1 [I>2σ(I)] | 0.0635 |
| wR2 (all data) | 0.1871 |
Table 2 is main bond distance's () and the bond angle [°] of title complex
*
| Zn(1)-O(1W) | 1.973(8) | Zn(1)-O(2) | 2.052(7) |
| Zn(1)-O(1) | 2.257(6) | Zn(2)-O(8) | 1.929(8) |
| Zn(2)-O(5) #2 | 1.940(7) | Zn(2)-O(3) | 1.965(7) |
| Zn(2)-N(1) | 2.019(9) | ||
| O(1W) #1-Zn(1)-O(1W) | 100.0(5) | O(1W) #1-Zn(1)-O(2) #1 | 165.7(3) |
| O(1W)-Zn(1)-O(2) #1 | 87.4(3) | O(2) #1-Zn(1)-O(2) | 88.0(4) |
| O(1W) #1-Zn(1)-O(1) | 94.7(3) | O(1W)-Zn(1)-O(1) | 93.4(3) |
| O(2) #1-Zn(1)-O(1) | 97.0(3) | O(2)-Zn(1)-O(1) | 73.7(2) |
| O(1)-Zn(1)-O(1) #1 | 167.4(3) | O(8)-Zn(2)-O(5) #2 | 106.1(3) |
| O(8)-Zn(2)-O(3) | 116.4(3) | O(5) #2-Zn(2)-O(3) | 116.9(3) |
| O(8)-Zn(2)-N(1) | 96.9(4) | O(5) #2-Zn(2)-N(1) | 107.6(4) |
| O(3)-Zn(2)-N(1) | 110.8(3) |
*symmetrical code:
#1– x, y ,-z+2;
#2– x, y+1 ,-z+2.
Claims (3)
1. chirality naphthyl oxalic acid and the preparation method of two (triazole) Zn complex, is characterized in that concrete steps are as follows: get equimolar zinc acetate, H
2l and btb puts into tetrafluoroethylene reactor, is that water and the ethanol of 7:1 and 6:2 is mixed solvent with volume ratio, places in an oven, is heated to 100 DEG C of constant temperature 72 hours, then slowly drops to room temperature and obtains.
2. method according to claim 1, is characterized in that concrete steps are as follows: zinc acetate 0.05 mmol, (S)-(-)-1, l '-bis-naphthyl-2,2 '-oxalic acid (H
2l) 0.05 mmol and 1, two (triazole) (btb) 0.05 mmol of 6-hexyl puts into tetrafluoroethylene reactor, with 7 mL water and 1 mL ethanol for mixed solvent, places in an oven, be heated to 100 DEG C of constant temperature 72 hours, then slowly drop to room temperature and get final product.
3. chiral metal complex according to claim 1, is characterized in that: chemical formula is [Zn
3(L)
3(btb) (H
2o)
2], its crystal belongs to oblique system, spacer is C2, unit cell parameters is a=26.7280 (5), b=9.4040 (3), c=17.3890 (6), α=90 °, β=102.582 (5) °, γ=90 °, V=4265.8 (2)
3, title complex is laminate structure.
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|---|---|---|---|
| CN201410634399.9A CN104370949B (en) | 2014-11-13 | 2014-11-13 | Chiral naphthyl oxalic acid with it is double（Triazole）Zn complex and preparation method thereof |
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|---|---|---|---|
| CN201410634399.9A CN104370949B (en) | 2014-11-13 | 2014-11-13 | Chiral naphthyl oxalic acid with it is double（Triazole）Zn complex and preparation method thereof |
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| CN104370949B CN104370949B (en) | 2017-05-31 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491988A (en) * | 2011-12-06 | 2012-06-13 | 南开大学 | Zinc-cluster porous luminescent complex, and preparation method and application thereof |
| CN103159790A (en) * | 2013-03-27 | 2013-06-19 | 洛阳师范学院 | Luminescent microporous polymer as material and method for preparing same |
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2014
- 2014-11-13 CN CN201410634399.9A patent/CN104370949B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102491988A (en) * | 2011-12-06 | 2012-06-13 | 南开大学 | Zinc-cluster porous luminescent complex, and preparation method and application thereof |
| CN103159790A (en) * | 2013-03-27 | 2013-06-19 | 洛阳师范学院 | Luminescent microporous polymer as material and method for preparing same |
Non-Patent Citations (2)
| Title |
|---|
| JIYONG HU ET AL.: "Construction of several d10 metal coordination polymers based on aromatic polycarboxylate and flexible triazole-based ligand", 《INORGANICA CHIMICA ACTA》 * |
| 胡冬华: "基于三氮唑及衍生物配体构筑的配位聚合物的合成与结构研究", 《中国博士学位论文全文数据库 工程科技Ⅰ辑》 * |
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