CN104370949B - Chiral naphthyl oxalic acid with it is double（Triazole）Zn complex and preparation method thereof - Google Patents
Chiral naphthyl oxalic acid with it is double（Triazole）Zn complex and preparation method thereof Download PDFInfo
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- CN104370949B CN104370949B CN201410634399.9A CN201410634399A CN104370949B CN 104370949 B CN104370949 B CN 104370949B CN 201410634399 A CN201410634399 A CN 201410634399A CN 104370949 B CN104370949 B CN 104370949B
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- triazole
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- oxalic acid
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 title claims abstract description 24
- -1 naphthyl oxalic acid Chemical compound 0.000 title claims abstract description 13
- 235000006408 oxalic acid Nutrition 0.000 title claims abstract description 11
- 150000003852 triazoles Chemical class 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000010668 complexation reaction Methods 0.000 title abstract description 3
- 239000000126 substance Substances 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract 2
- 239000011701 zinc Substances 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 7
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 6
- 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
- 239000004246 zinc acetate Substances 0.000 claims description 5
- 230000003247 decreasing effect Effects 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 239000012467 final product Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 5
- 150000001450 anions Chemical class 0.000 abstract description 3
- 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 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 230000005595 deprotonation Effects 0.000 abstract description 2
- 238000010537 deprotonation reaction Methods 0.000 abstract description 2
- 239000002178 crystalline material Substances 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 238000012827 research and development 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
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 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
- 241000208340 Araliaceae Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- MOFINMJRLYEONQ-UHFFFAOYSA-N [N].C=1C=CNC=1 Chemical class [N].C=1C=CNC=1 MOFINMJRLYEONQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229920001795 coordination polymer Polymers 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 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
- 230000001052 transient effect Effects 0.000 description 1
- 238000004846 x-ray emission Methods 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
- 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
A kind of chiral double naphthyl oxalic acid are double with hexyl（Triazole）Zn complex and preparation method thereof, belongs to technical field of chemistry, and complex is following chemical formula：[Zn3(L)3(btb)(H2O)2], wherein L is (S) () 1 of deprotonation, and the diethyl acid anion of 1 ' double naphthyls 2,2 ', btb is double 1,6 hexyls（Triazole）.Complex is prepared using solvent thermal process.Complex of the invention is demonstrated by fluorescent emission intensity high, and the crystalline material of acquisition can obtain further research and development application in fluorescent material field.
Description
Technical field
The invention belongs to technical field of chemistry, and in particular to a kind of transient metal complex and preparation method thereof.
Background technology
Chiral coordination polymer is due to potentially should at aspects such as molecular recognition, catalysis, optical material and biomimetic chemistries
It is widely studied with value（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, such as 1,1 '-diphenol and 1,1 '-bisnaphthol is often used as chiral template to construct chirality
Complex（M. Canlica, T. Nyokong,Dalton Trans2011,40, 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）.With
Traditional complex is compared, and the research of chiral coordination compound is still less, is based especially on chiral organic carboxyl acid and the miscellaneous neutral ligands of N
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 Des2014,14, 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,CrystEngComm2014,16, 7673）.
We have chosen chiral 1,1 '-bis--beta naphthal oxalic acid first（H2L）It is double with 1,6- hexyls（Triazole）（btb）
It is research object, the metal complex research based on this mixed ligand is also unmanned so far to be reported.
H2L and btb parts.
The content of the invention
The purpose of the present invention is that a kind of open chiral double naphthyl oxalic acid are double with hexyl（Triazole）Zn complex.
The present invention also discloses the preparation method of this chiral zinc nitrogen complexes.
The chiral zinc nitrogen complexes of double naphthyl oxalic acid have following chemical formula, i.e.,：[Zn3(L)3(btb)(H2O)2], wherein L
It is (S)-(-) -1, l '-bis- naphthyl -2 of deprotonation, 2 '-oxalic acid anion ligand, btb is double 1,6- hexyls（Three nitrogen
Azoles）.
Complex crystal belongs to monoclinic system, and space group is C2, and cell parameter is a=26.7280 (5), and b=
9.4040 (3), c=17.3890 (6), α=90 °, β=102.582 (5) °, γ=90 °, V=4265.8 (2)
Å3, complex is in layer structure.
The preparation method of the chiral zinc nitrogen complexes of described double naphthyl oxalic acid, comprises the following steps：
The synthesis of the chiral zinc nitrogen complexes of double naphthyl oxalic acid：Take equimolar zinc acetate, H2L and btb are put into polytetrafluoro
It is 7 with volume ratio in ethylene reaction kettle：1 and 6：2 water and ethanol is mixed solvent, is placed in an oven, is heated to 100 DEG C
Constant temperature 72 hours, is then slowly decreased to room temperature and is obtained.
Chiral zinc nitrogen complexes preparation method of the present invention is simple, repeatability is strong, properties of product stabilization.
Fluorescence data shows that complex of the invention has the fluorescence property of stabilization, can be as fluorescent material in material
Material scientific domain is applied.
Brief description of the drawings
Fig. 1 is the coordination context diagram of metal in complex；
Fig. 2 is two-dimensional layered structure figure；
Fig. 3 is the fluorescence emission spectrogram of compound of complex；
Fig. 4 is the fluorescent quenching curve map of complex；
Fig. 5 is the powder diagram of complex.
Specific embodiment
Embodiment 1
By zinc acetate 0.05 mmol, H2It is anti-that the mmol of L 0.05 and the mmol of btb 0.05 are put into 15 mL polytetrafluoroethylene (PTFE)
Answer in kettle, be mixed solvent with 7 mL water and 1 mL ethanol, place in an oven, be heated to 100 DEG C of constant temperature 72 hours, then
It is slowly decreased to room temperature, yield 32%.
Embodiment 2
By zinc acetate 0.05 mmol, H2It is anti-that the mmol of L 0.05 and the mmol of btb 0.05 are put into 15 mL polytetrafluoroethylene (PTFE)
Answer in kettle, be mixed solvent with 6 mL water and 2 mL ethanol, place in an oven, be heated to 100 DEG C of constant temperature 72 hours, then
It is slowly decreased to room temperature, yield 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 complex
（1）The crystal structure determination of complex
The diffraction data of complex is collected on Oxford Diffraction Gemini R Ultra diffractometers, Mo
KαRay (λ=0.71069), 293 K.Scanned using technology and be corrected.Crystal structure is by SHELEXL-97 journeys
Sequence is solved with direct method, and refine is carried out using SHELEXL-97 with complete matrix least square method.The temperature factor of non-hydrogen atom is used
Anisotropy is modified.Detailed axonometry data are shown in Table 1；Important bond distance and bond angle data is shown in Table 2；Crystal structure is shown in
Fig. 1-Fig. 2.
It is characterized in that the complex crystal belongs to monoclinic system, space group is C2/c, structure cell ginseng for the complex of invention
Number 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, one and half L anion, half are included in complex unit cell
Individual btb parts and a water of coordination molecule.Zn1 is located at reversion center, is the octoploids structure for slightly distorting；Zn2 is tetrahedron structure
Type.Zn (II) ions are connected as layer structure by L anion and btb parts.
（2）The photoluminescent property research of complex（FLSP920 Edinburgh XRFs）.
When 330 nm are excited, complex has the last one emission peak at 370 nm（Fig. 3）, to the fluorescence decay song of complex
Line is fitted, and fluorescence lifetime isτ 1= 0.59 ns（87.76%）Withτ 2= 2.58 ns（12.24%）（Fig. 4）.
Table 1 is the predominant crystal data of complex
| formula | C82H68N6O20Zn3 |
| Mr | 1653.53 |
| crystal system | monoclinic |
| space group | C2 |
| a (Å) | 26.7280(5) |
| b (Å) | 9.4040(3) |
| c (Å) | 17.3890(6) |
| α(°) | 90 |
| β(°) | 102.582(5) |
| γ(°) | 90 |
| V (Å3) | 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 |
Main bond distance () and bond angle [°] of the table 2 for 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. a kind of chiral naphthyl oxalic acid with it is double（Triazole）The preparation method of Zn complex, it is characterised in that：Take equimolar
Zinc acetate, H2L and btb are put into ptfe autoclave, are 7 with volume ratio：1 or 6：2 water and ethanol is mixed
Bonding solvent, places in an oven, is heated to 100 DEG C of constant temperature 72 hours, is then slowly decreased to room temperature and is obtained；
Described btb is double 1,6- hexyls（Triazole）；
Described H2L structural formulas are：
2. according to claim 1 a kind of chiral naphthyl oxalic acid with it is double（Triazole）The preparation method of Zn complex, it is special
Levy and be：Zinc acetate 0.05 mmol, H2Mmol the and btb 0.05mmol of L 0.05 are put into ptfe autoclave,
It is mixed solvent with 7 mL water and 1 mL ethanol, places in an oven, be heated to 100 DEG C of constant temperature 72 hours, then slowly
Room temperature is dropped to obtain final product.
3. a kind of chiral naphthyl oxalic acid according to claim 1 with it is double（Triazole）Zn complex, it is characterised in that：
Chemical formula is [Zn3(L)3(btb)(H2O)2], its crystal belongs to monoclinic system, and space group is C2, cell parameter be 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, complex is in layer structure.
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