CN100516072C - Cadmium anthracene-9,10-dicarboxylate complex, preparing method and application thereof - Google Patents
Cadmium anthracene-9,10-dicarboxylate complex, preparing method and application thereof Download PDFInfo
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- CN100516072C CN100516072C CNB2007100568202A CN200710056820A CN100516072C CN 100516072 C CN100516072 C CN 100516072C CN B2007100568202 A CNB2007100568202 A CN B2007100568202A CN 200710056820 A CN200710056820 A CN 200710056820A CN 100516072 C CN100516072 C CN 100516072C
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- dianthracene
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Abstract
The invention discloses a synthesizing method and application of 9, 10-dianthracene chromium complex, whose chemical formula of complex is {[Cd2(L)2(H2O)4](C2H5OH)(H2O)1.25} infinity, wherein L is 9, The invention discloses a synthesizing method and application of 9, 10-dianthracene chromium complex, whose chemical formula of complex is {[Cd2(L)2(H2O)4](C2H5OH)(H2O)1.25} infinity, wherein L is 9, 10-dianthracene dicarboxyl anion complex; the complex is made by dispersing method, which is different from normal d10 metal carboxyl complex to overcome high temperature and danger with high receivin10-dianthracene dicarboxyl anion complex; the complex is made by dispersing method, which is different from normal d10 metal carboxyl complex to overcome high temperature and danger with high receiving rate and repeatable property; the fluorescent spectrum data and femtosecond laser system detects fluorescent lifetime data, which displays stable fluorescent property for complex as fluorescent mateg rate and repeatable property; the fluorescent spectrum data and femtosecond laser system detects fluorescent lifetime data, which displays stable fluorescent property for complex as fluorescent material. rial.
Description
Technical field
The present invention relates to transition metal complex material field, especially a kind of 9,10-dianthracene acid cadmium complex and preparation method, described title complex has three-dimensional α-Po (4
6) network structure, its photoluminescent property makes it can be used as fluorescent material and is applied.
Background technology
In recent years the d10 metal complexes because have novel structure and potential high-performance (as: fluorescence, fractionation by adsorption, electricity lead and catalysis etc.) be subjected to people very big concern and by a large amount of synthetic and research, one of focus (J.-M.Lehn, Supramolecular Chemistry are studied in the forward position that also becomes simultaneously coordination chemistry; VCH:Weinheim, 1995; V.W.W.Yam, K.K.-W.Lo, W.K.-M.Fung, C.-R.Wang, Coord.Chem.Rev.1998,171,17-41; S.Leininger, B.Olenyuk, P.J.Stang, Chem.Rev.2000,100,853-908; S.Wang, Coord.Chem.Rev.2001,215,79-98; O.R.Evans, W.Lin, Acc.Chem.Res.2002,35,511-522; P.J.Steel, Acc.Chem.Res.2005,38,243-250; B.-H.Ye, M.-L.Tong, X.-M.Chen, Coord.Chem.Rev.2005,249,545-565).Have the carboxylic acid part that enriches coordination mode, particularly fragrance contains benzene, naphthalene-ring containing two or many carboxyls part by the extensive and a large amount of research of people (as: Wang, X.-L.; Qin, C.; Wang, E.-B.; Su, Z.-M.Chemistry-A European Journal, 2006,12,2680-2691; Sang, R.-L.; Li, X.Inorganica Chimica Acta 2006,359,525-532; Xiao, D.-R.; Wang, E.-B.; An, H.-Y.; Su, Z.-M.; Li, Y.-G.; Gao, L.; Sun, C.-Y.; Xu, L. Chemistry--A European Journal2005,11,6673-6686; Wen, L.; Li, Y.; Dang, D.; Tian, Z.; Ni, Z.; Meng, Q.Journal of SolidState Chemistry 2005,178,3336-3341; Du, M.; Jiang, X.-J.; Zhao, X.-J..ChemicalCommunications 2005,44,5521-5523; Thirumurugan, A.; Rao, C.N.R.JournalofMaterials Chemistry 2005,15,3852-3858; Rosi, N.L.; Kim, J.; Eddaoudi, M.; Chen, B.; O ' Keeffe, M.; Yaghi, O.M.Journal of the American Chemical Society 2005,127,1504-1518; Shi, X.; Zhu, G.; Wang, X.; Li, G.; Fang, Q.; Zhao, X.; Wu, G.; Tian, G.; Xue, M.; Wang, R.; Qiu, S.Crystal Growth﹠amp; Design 2005,5,341-346; Shi, X.; Zhu, G.; Wang, X.; Li, G.; Fang, Q.; Wu, G.; Tian, G.; Xue, M.; Zhao, X.; Wang, R.; Qiu, S.Crystal Growth﹠amp; Design 2005,5,207-213; Zou, R.-Q.; Bu, X.-H; Zhang, R.-H.Inorganic Chemistry 2004,43,5382-5386; Dai, J.-C.; Wu, X.-T.; Fu, Z.-Y.; Hu, S.-M.; Du, W.-X.; Cui, C.-P.; Wu, L.-M.; Zhang, H.-H.; Sun, R.-Q.Chemical Communications 2002,12-13; ).
With above-mentioned mention contain benzene, naphthalene-ring containing carboxylic acid part is compared, and contains the anthracene nucleus series carboxylic acid part of more volume fragrance skeleton, particularly 9, the acid of 10-dianthracene, its d
10Still seldom (information source SciFinder Scholar Searching ends on October 15th, 2006 in the research of metal complexes; M.J.Byrnes, M.H.Chisholm, D.F.Dye, C.M.Hadad, B.D.Pate, P.J.Wilson, J.M.Zaleski, DaltonTrans.2004,523-529).From us previous studies (X.-H.Bu, M.-L Tong, H.-C.Chang, S.Kitagawa, S.R.Batten, Angew.Chem.Int.Ed.2004,43,192-195; C.-S.Liu, X.-S.Shi, J.-R.Li, J.-J.Wang, X.-H.Bu, Crvst.Growth Des.2006,6,656-663; R.-Q.Zou, C.-S.Liu, X.-S.Shi, X.-H.Bu, J.Ribas, CrystEngComm.2005,7,722-727; X.-H.Bu, M.-L.Tong, Y.-B.Xie, J.-R.Li, H.-C.Chang, S.Kitagawa, J.Ribas, Inorg.Chem.2005,44,9837-9846), this type of large volume fragrance skeleton carboxylic acid part with contain benzene, naphthalene-ring containing carboxylic acid part is compared has following tangible characteristics: (1) has bigger conjugated pi system, therefore π when constructing the corresponding metal title complex ... pi accumulation and C-H ... π interacts may play important effect, particularly enters the more supramolecule network facet of higher-dimension at limited multinuclear subunit and the low-dimensional molecular entity of connection; (2) the volume obstacle of anthracene nucleus exerts an influence to the coordination mode and the ability of carboxyl, but also is in the network from the angle of crystal engineering weak interaction and molecular geometry and internetwork π ... pi accumulation and C-H ... the condition that the interactional formation of π is provided convenience; (3) containing greatly, the anthracene nucleus of conjugated pi system is good fluorescent signal chromophoric group, so containing the synthetic of this type of ligand-complexes also is that fluorescent material and further exploitation (as: electroluminescent, chemical sensor, fluorescence PET transmitter) of using thereof provide possibility (A.J.Eastwood, A.E.A.Contoret, S.R.Farrar, S.Fowler, S.M.Kelly, S.M.Khan, J.E.Nicholls, M.O ' Neill, Syntheticmetals 2001,121,1659-1660; M.A.Bernardo, F.Pina, B.Escuder, E.Garc í a-
, M.L.Godino-Salido, J.Latorre, S.V. Luis, J.A.Ram í rez, C.Soriano, J.Chem.Soc., DaltonTrans.1999,915-921; B.Bag, P.K.Bharadwaj, J.Phys.Chem.B 2005,109,4377-4390; K.Kubo, A Mori, J.Mater.Chem.2005,15,2902-2907; A.Tamayo, C.Lodeiro, L.Escriche, J.Casab ó, B.Covelo, P.Gonz á lez, Inorg.Chem.2005,44,8105-8115).Therefore, this type of title complex has wide space aspect the further research and development of structural research and performance.
Summary of the invention
The objective of the invention is to disclose a kind of 9,10-dianthracene acid cadmium complex, the simple and easy to do synthetic method of this title complex and the application of title complex thereof.
It is a kind of 9 that technical scheme of the present invention provides, and 10-dianthracene acid cadmium complex is characterized in that title complex is the title complex of following chemical formula: { [Cd
2(L)
2(H
2O)
4] (C
2H
5OH) (H
2O)
1.25}
∞, L=9 wherein, the two carboxyl anions of 10-dianthracene acid, its molecular formula is as follows:
The synthetic employing diffusion process of title complex of the present invention: under the room temperature, cadmium metal salt is placed the test tube bottom, add a small amount of dissolved in distilled water.The mixing solutions that adds ethanol and water in the above; The superiors' adding is dissolved with 2, the ethanolic soln of the ligand L of 6-lutidine; Leave standstill diffusion then and obtained yellow bulk-shaped monocrystal in 20-30 days, successively with distilled water, ethanol and ether washing, drying obtains again.
The present invention 9, the fluorescent chemicals of 10-dianthracene acid cadmium complex aspect material as the application of fluorescent material.
The synthetic method of title complex provided by the invention is different from the d commonly used that reports in the present document
10The synthetic methods such as hydro-thermal of carboxylate metal class ligand-complexes, overcome its temperature height, dangerous big, productive rate is low and the technological deficiency of repeatable difference.The synthetic method that the present invention represents, mild condition, productive rate height, reproducibility are good.The fluorescence lifetime data that the fluorescence data of crystal prototype and fs-laser system detect show that all this type of title complex has the stable fluorescence performance, can be used as fluorescent material and is applied at material science.
Description of drawings
The Cd coordination environment figure of Fig. 1 title complex;
Three-dimensional α-the Po (4 of Fig. 2 title complex
6) the NE synoptic diagram;
The solid fluorescence figure of Fig. 3 title complex;
The solid fluorescence life diagram of Fig. 4 title complex;
The powdery diffractometry synoptic diagram of Fig. 5 title complex.
Embodiment
Complex crystal of the present invention belongs to rhombic system, and spacer is Pbca, and unit cell parameters is a=16.662 (3), b=20.948 (4), c=21.055 (4)
, α=90, β=90, γ=90 °, V=7349 (3)
3Basic structure is a three-dimensional α-Po (4
6) network structure, there are two kinds of obstructed Cd center coordination environments, as for L
1Part has then represented the two monodentates of bridging and bridging two kinds of coordination modes of tooth in pairs.Also have free ethanol and water molecules bag to be connected in the space of three-dimensional network.
In the preparation method of title complex of the present invention, cadmium metal salt is dissolved in distilled water, and to make the concentration of solution be 0.02~0.04molL
-1The volume ratio of the mixing solutions of ethanol and water is 1: 1-1: 1.2; Ligand L is dissolved in that to make strength of solution in the ethanol be 0.01~0.02molL
-1The mol ratio of ligand L and metal-salt is 1: 2; Add 0.03-0.05ml 2,6-lutidine in the ethanolic soln of ligand L; The volume ratio of upper, middle and lower-ranking solution is 1: 3: 1-1: 4: 1.
The preparation of embodiment 1 title complex
With 0.1mmol Cd (NO
3)
26H
2O places the test tube bottom, uses the 5mL dissolved in distilled water, the middle mixed solution 15ml that adds 1: 1 volume ratio of ethanol/water; 0.05mmol H
2L
1, use the 5mL dissolve with ethanol, it is excessive 2 to add, and 6-lutidine 0.05mL places the test tube upper strata.Sealing and standing 25 days, yellow bulk-shaped monocrystal appears in the place, boundary that connects of solution interface on the test tube wall.Crystal washs with distilled water, ethanol and ether successively, vacuum-drying, and productive rate is about 50%.
Main infrared absorption peak is: 3362s (br), 3046w (br), 2360w, 1945w, 1825w, 1562vs, 1443s, 1323s, 1281s, 1083m, 1042w, 1025w, 900w, 876w, 839s, 774m, 733w, 685m, 600w, 463w.
The preparation of embodiment 2 title complexs
With 0.1mmol Cd (ClO
4)
26H
2O places the test tube bottom, uses the 5mL dissolved in distilled water; The middle mixed solution 15ml that adds 1: 1.2 volume ratio of ethanol/water; 0.05mmol H
2L
1, use the 5mL dissolve with ethanol, it is excessive 2 to add, and 6-lutidine 0.05mL places the test tube upper strata.Sealing and standing 28 days, yellow bulk-shaped monocrystal appears in the place, boundary that connects of solution interface on the test tube wall.Crystal washs with distilled water, ethanol and ether successively, vacuum-drying, and productive rate is 55%.
Main infrared absorption peak is: 3362s (br), 3046w (br), 2360w, 1945w, 1825w, 1562vs, 1443s, 1323s, 1281s, 1083m, 1042w, 1025w, 900w, 876w, 839s, 774m, 733w, 685m, 600w, 463w.
The preparation of embodiment 3 title complexs
With 0.1mmol CdSO
4Place the test tube bottom, use the 4mL dissolved in distilled water; The middle mixed solution 16ml that adds 1: 1 volume ratio of ethanol/water; 0.05mmol H
2L
1, use the 4mL dissolve with ethanol, it is excessive 2 to add, and 6-lutidine 0.05mL places the test tube upper strata.Sealing and standing 33 days, yellow bulk-shaped monocrystal appears in the place, boundary that connects of solution interface on the test tube wall.Crystal washs with distilled water, ethanol and ether successively, vacuum-drying, and productive rate is 52%.
Main infrared absorption peak is: 3362s (br), 3046w (br), 2360w, 1945w, 1825w, 1562vs, 1443s, 1323s, 1281s, 1083m, 1042w, 1025w, 900w, 876w, 839s, 774m, 733w, 685m, 600w, 463w.
The preparation of embodiment 4 title complexs
With 0.1mmol Cd (NO
3)
26H
2O places the test tube bottom, uses the 5mL dissolved in distilled water, the middle mixed solution 15ml that adds 1: 1 volume ratio of ethanol/water; 0.05mmol H
2L
1, use the 5mL dissolve with ethanol, it is excessive 2 to add, and 6-lutidine 0.05mL places the test tube upper strata.Sealing and standing 30 days, yellow bulk-shaped monocrystal appears in the place, boundary that connects of solution interface on the test tube wall.Crystal washs with distilled water, ethanol and ether successively, vacuum-drying, and productive rate is 55%.
Main infrared absorption peak is: 3362s (br), 3046w (br), 2360w, 1945w, 1825w, 1562vs, 1443s, 1323s, 1281s, 1083m, 1042w, 1025w, 900w, 876w, 839s, 774m, 733w, 685m, 600w, 463w.
The relevant characterization of embodiment 5 title complexs
(1) crystal structure determination of title complex
The monocrystalline of choosing suitable size at microscopically at room temperature carries out the X-ray diffraction experiment.On Bruker Smart1000CCD diffractometer, use Mo-K through the graphite monochromator monochromatization
αRay (λ=0.71073
), with
Mode is collected diffraction data.Carry out reduction of data with Bruker SAINT program.The diffraction data of part-structure carries out absorption correction with the SADABS program.Crystalline structure is solved in conjunction with difference Fourier is synthetic by direct method.All non-hydrogen atom coordinate and anisotropic parameters carry out the complete matrix least-squares refinement, and the hydrogen atom position is determined by theoretical mode computation.Hydrogen atom on partial solvent water and the ethanol is handled with the method for difference Fourier peak-seeking.Detailed axonometry data see Table 1.Structure is seen Fig. 1-2.Fig. 1: the Cd coordination environment figure of title complex; Fig. 2: the three-dimensional α-Po (4 of title complex
6) the NE synoptic diagram;
(2) the solid fluorescence character of title complex
Complex crystal sample after enrichment is handled is through further milled processed, and carry out the test of solid fluorescence: title complex excites at the 426nm place, obtains maximum emission peak at the 467nm place, sees Fig. 3.(instrument model: JOBINYVON (HORIBA) FLUOROMAX-P).
(3) the fluorescence lifetime research of title complex
Title complex uses the femtosecond laser detection system at the maximum emission wavelength place, and detected fluorescence lifetime is 0.449ns, sees Fig. 4.(instrument model: femtosecond laser detection system Spectra-Physics Corp).
(4) the phase purity of title complex characterizes
The XPRD of title complex characterizes and shows that it has reliable phase purity, for its application as fluorescent material provides assurance.See Fig. 5.(instrument model: Rigaku D/Max-2500).
The main crystallographic data of table 1 title complex.
aR=∑(||F
0|-|F
C||)/∑|F
0|;
bwR=[∑w(|F
0|
2-|F
C|
2)
2/∑w(F
0 2)]
1/2。
Claims (10)
1 one kind 9, the cadmium complex of 10-dianthracene acid part is characterized in that title complex is the title complex of following chemical formula: { [Cd
2(L)
2(H
2O)
4] (C
2H
5OH) (H
2O)
1.25}
∞, L=9 wherein, the two carboxyl anion parts of 10-dianthracene acid, its molecular formula is as follows:
3 claims 1 are described 9, and the preparation method of the cadmium complex of 10-dianthracene acid part is characterized in that it comprises the steps: under the room temperature, and cadmium metal salt is placed the test tube bottom, adds dissolved in distilled water; The mixing solutions that adds ethanol and water in the above; The superiors' adding is dissolved with 2, the ethanolic soln of the ligand L of 6-lutidine; Leave standstill diffusion then and obtained yellow bulk-shaped monocrystal in 20-30 days, successively with distilled water, ethanol and ether washing, drying obtains again.
4 preparation methods according to the described title complex of claim 3, it is characterized in that being dissolved in distilled water for cadmium metal salt, to make the concentration of solution be 0.02~0.04molL
-1
5 preparation methods according to the described title complex of claim 3, the volume ratio that it is characterized in that the mixing solutions of ethanol and water is 1: 1-1: 1.2.
6 preparation methods according to the described title complex of claim 3 is characterized in that it is 0.01~0.02molL that ligand L is dissolved in the concentration of making solution in the ethanol
-1
7 preparation methods according to claim 3 or 6 described title complexs, the mol ratio that it is characterized in that ligand L and metal-salt is 1: 2.
8 preparation methods according to the described title complex of claim 7 is characterized in that adding in the ethanolic soln of ligand L 0.03-0.05ml 2,6-lutidine.
9 preparation methods according to claim 3,4 or 5 described title complexs, the volume ratio that it is characterized in that said upper, middle and lower-ranking solution is 1: 3: 1-1: 4: 1.
10 according to the fluorescent chemicals of the described title complex of claim 1 aspect the material as the application of fluorescent material.
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CN101406826B (en) * | 2008-11-17 | 2010-06-09 | 南开大学 | Coordination polymer having solvent selectivity reversible adsorption and preparation method thereof |
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CN103012449A (en) * | 2011-09-22 | 2013-04-03 | 中国科学院福建物质结构研究所 | 4-hydroxycoumarin-containing cadmium-inserted fluorescent material and synthesis method thereof |
CN104592261B (en) * | 2015-02-26 | 2016-08-10 | 天津师范大学 | Phenyl triiodide amine three triazole zinc chloride coordination compound with potential fluorescent material and preparation method thereof |
CN104610316A (en) * | 2015-02-26 | 2015-05-13 | 天津师范大学 | Fluorescent material containing 3-iodo-aniline-3,3-azole cadmium perchlorate complex and preparation method thereof |
CN116693868B (en) * | 2023-05-10 | 2024-05-10 | 苏州大学 | Singlet oxygen capturing or releasing material and preparation method and application thereof |
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Title |
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两个由1,1'-环己烷二乙酸构筑的镉的配合物的合成,晶体结构何荧光性质. 何锦润,王玉玲,毕文华,曹荣.无机化学学报,第22卷第8期. 2006 |
两个由1,1'-环己烷二乙酸构筑的镉的配合物的合成,晶体结构何荧光性质. 何锦润,王玉玲,毕文华,曹荣.无机化学学报,第22卷第8期. 2006 * |
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