CN101402645A - Benzimidazolyl-acridine ligand CuI complex and method of preparing the same - Google Patents
Benzimidazolyl-acridine ligand CuI complex and method of preparing the same Download PDFInfo
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- CN101402645A CN101402645A CNA200810153106XA CN200810153106A CN101402645A CN 101402645 A CN101402645 A CN 101402645A CN A200810153106X A CNA200810153106X A CN A200810153106XA CN 200810153106 A CN200810153106 A CN 200810153106A CN 101402645 A CN101402645 A CN 101402645A
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- acridine
- benzimidazolyl
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Abstract
The invention discloses a CuI complex of a benzimidazolyl-acridine ligand, which aims at jointly introducing benzimidazole and acridine ring into the CuI complex and is a ligand through construction. The chemical formula of the complex is Cu4I4L4, wherein, L refers to 1-benzimidazolyl 9-acridine. The preparation method of the complex comprises the steps: the 1-benzimidazolyl 9-acridine is dissolved into CHCl3 at the normal temperature and placed at the bottom of a test tube; a CHCl3/CH3CN mixed solution is added to form an intermediate layer; CH3CN saturated solution of CuI is added to form an upper layer; and after the obtained solution stands still and diffuses for 30 days to 35 days, orangered massive single crystals can be obtained and then are dried after being washed with CHCl3. The CuI complex has the advantages that the complex is easy to prepare; the obtained crystals have higher purity; and the complex has stable fluorescence emission, characteristic adsorption, long transmitted wave and higher lighting strength, can be applied as fluorescent materials and opens up a new way for exploring novel fluorescent materials.
Description
(1) technical field
The present invention relates to transition metal complex material field, especially a kind of benzimidazolyl-acridine ligand CuI complex and preparation method thereof.
(2) background technology
Because d
10The closedshell transition metal complex has the advantages that structure is various and photoluminescent property is abundant, is widely studied in recent years.CuI becomes fabulous inorganic functional module because of forming class cubane structure and have abundant optical property in title complex, existing correlative study [M.Vitale and P.C.Ford, Coord.Chem.Rev., 2001 in the coordination chemistry field, 219-221,3.; K.R.Kyle, C.K.Ryu, J.A.DiBenedetto and P.C.Ford, J.Am.Chem.Soc., 1991,113,2954; A.Vega and J.-Y.Saillard, Inorg.Chem., 2004,43,4012.; C.K.Ryu, M.Vitaleand P.C.Ford, Inorg.Chem., 1993,32,869; E.Cariati, J.Bourassa and P.C.Ford, Chem.Commun., 1998,32,1623; E.Cariati, X.Bu and P.C.Ford, Chem.Mater., 2000,12,3385.].The N atom of benzoglyoxaline has stronger coordination ability, energy and multiple metallic ion coordination, under strong coordinate bond, weak hydrogen bond and π-π effect, can assemble out various metal complexess [Rom á n-Alpiste M.J., the Mart í n-Ramos J.D. of novel structure and unique properties
-Campos A.J., et al.Polyhedron, 1999,18,3341.; Xie L.X., Wei Y.L., Wang Y.F., et al.Mol.Struct, 2004,602,201.; Hu R.F., Zhang J., Kang Y., et al.Inorg.Chem.Commun., 2005,8,828.; Reisner E., Arion V.B., Eichinger A., et al.Inorg.Chem., 2005,44,6704.; Murrie M., Collison D., Garner C.D., et al.Polyhedron, 1998,17,3031.].Acridine ring system row part has big conjugated pi system, often easily form good pi-pi accumulation effect when forming title complex, thereby assemble has the super molecular compound of potential application performance.[Ivana?Sloufovaa，Miroslav?Sloufb，ACTA?C，2000，C56(11)，1312.；Xian-He?Bu，Ming-Liang?Tong，Ya-Bo?Xie，et?al.Inorg.Chem.，2005，44，9837-9846.；Xian-He?Bu，Ming-Liang?Tong，Ho-Chol?Chang，et?al.Angew.Chem.Int.Ed.，2004，43，192-195.]。Benzimidazole and acridine ring are introduced same part jointly and constructed the corresponding metal title complex, have not yet to see report.
(3) summary of the invention
The objective of the invention is at above-mentioned situation, absorption and emission wavelength and higher luminous intensity and the benzimidazolyl-acridine ligand CuI complex that is easy to prepare and preparation method thereof of having stable fluorescence-emission character, feature under a kind of normal temperature are provided.
Technical scheme of the present invention:
A kind of benzimidazolyl-acridine ligand CuI complex is characterized in that: for benzimidazole and acridine ring are introduced the CuI part jointly and constructed the title complex of formation, this title complex can be used following chemical formulation: Cu
4I
4L
4, wherein L is a 1-benzimidazolyl-9-acridine, the molecular formula of L is:
A kind of preparation method of benzimidazolyl-acridine ligand CuI complex is characterized in that step is as follows:: 1) at room temperature, 1-benzimidazolyl-9-acridine is dissolved in CHCl
3In, obtain CHCl
3Solution and place test tube bottom to constitute lower floor; 2) in this test tube, add CHCl
3/ CH
3The CN mixing solutions constitutes the middle layer; 3) CH of adding CuI in this test tube
3The CN saturated solution constitutes the upper strata; 4) leave standstill diffusion 30-35 days, can obtain the orange bulk-shaped monocrystal; 5) with monocrystalline CHCl
3The washing after drying can make.
Described 1-benzimidazolyl-9-acridine is dissolved in CHCl
3Strength of solution be 0.01～0.02molL
-1
Described CHCl
3/ CH
3CN mixed liquor volume ratio is 1: 1～1.5.
The volume ratio of upper, middle and lower-ranking solution is 1: 6～8: 1 in the described test tube.
Advantage of the present invention is: described title complex is easy to preparation, the crystal purity that obtains is higher, the absorption and emission wavelength and the higher luminous intensity that have stable fluorescence-emission character, feature at normal temperatures can be used as fluorescent material and use, for new road has been opened up in the exploration of novel fluorescent material.
(4) description of drawings
Fig. 1 is the crystalline structure figure of this title complex.
Fig. 2 is the solid fluorescence figure of this title complex.
Fig. 3 is the powdery diffractometry XPRD figure of this title complex.
(5) embodiment
Synthesizing of 1-imidazolyl 9-acridine: take by weighing the 0.1342g benzoglyoxaline and place the 50ml round-bottomed flask, add 1.5ml10mol/L NaOH solution, being stirred to benzoglyoxaline all dissolves, add 10ml benzene, stirred 1 hour, add the 0.2211g9-chloro-acridine, drip the 1ml TBAH, reflux 72 hours.After reaction is finished, solution is transferred to separating funnel, with the 500ml washing, keeps organic layer, with 150ml chloroform extraction organic layer, drying is spin-dried for, and gets light yellow thick product.Carry out recrystallization with trichloromethane-normal hexane, suction filtration, oven dry gets 1-imidazolyl 9-acridine 0.1008g, productive rate 30%.
Embodiment 1:
With concentration is 0.017molL
-1The CHCl of 1-benzimidazolyl-9-acridine
3Solution places the test tube bottom; The middle CHCl that adds
3/ CH
3CN mixing solutions (1: 1) 18ml; The upper strata adds the CH of CuI
3CN saturated solution 3ml; Leave standstill diffusion and obtained the orange bulk-shaped monocrystal in 30 days; Crystal CHCl
3Washing, drying; Productive rate is 50%.The infrared analysis result shows: main infrared absorption peak is: 3065cm
-1, 1607cm
-1, 1553cm
-1, 1508cm
-1, 1501cm
-1, 1456cm
-1, 1437cm
-1, 1419cm
-1, 1305cm
-1, 1288cm
-1, 1222cm
-1, 1194cm
-1, 1145cm
-1, 1004cm
-1, 931cm
-1, 857cm
-1, 796cm
-1, 746cm
-1, 646cm
-1By the phase purity of XPRD detection title complex, the result is referring to Fig. 3.
Embodiment 2:
With concentration is 0.02molL
-1The CHCl of 1-benzimidazolyl-9-acridine
3Solution places the test tube bottom; The middle CHCl that adds
3/ CH
3CN mixing solutions (1: 1.25) 16ml; The upper strata adds the CH of CuI
3CN saturated solution 2ml; Leave standstill diffusion and obtained the orange bulk-shaped monocrystal in 35 days; Crystal CHCl
3Washing, drying; Productive rate is 45%.The infrared analysis result shows: main infrared absorption peak is: 3065cm
-1, 1607cm
-1, 1553cm
-1, 1508cm
-1, 1501cm
-1, 1456cm
-1, 1437cm
-1, 1419cm
-1, 1305cm
-1, 1288cm
-1, 1222cm
-1, 1194cm
-1, 1145cm
-1, 1004cm
-1, 931cm
-1, 857cm
-1, 796cm
-1, 746cm
-1, 646cm
-1
Embodiment 3:
With concentration is 0.013molL
-1The CHCl of 1-benzimidazolyl-9-acridine
3Solution places the test tube bottom; The middle CHCl that adds
3/ CH
3CN mixing solutions (1: 1.5) 17ml; The upper strata adds the CH of CuI
3CN saturated solution 3ml; Leave standstill diffusion and obtained the orange bulk-shaped monocrystal in 35 days; Crystal CHCl
3Washing, drying; Productive rate is 43%.The infrared analysis result shows: main infrared absorption peak is: 3065cm
-1, 1607cm
-1, 1553cm
-1, 1508cm
-1, 1501cm
-1, 1456cm
-1, 1437cm
-1, 1419cm
-1, 1305cm
-1, 1288cm
-1, 1222cm
-1, 1194cm
-1, 1145cm
-1, 1004cm
-1, 931cm
-1, 857cm
-1, 796cm
-1, 746cm
-1, 646cm
-1
The sign of this title complex is measured:
1) crystalline structure:
The monocrystalline of choosing suitable size at microscopically at room temperature carries out the X-ray diffraction experiment.On Bruker Smart 1000CCD diffractometer, use Mo-K through the graphite monochromator monochromatization
αRay (λ=0.71073
), with
-ω 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 C-H and N-H atom site are determined by theoretical mode computation.
Complex crystal belongs to tetragonal system, and spacer is I4 (1)/a, and unit cell parameters is: a=23.4032
B=23.4032
C=13.0773
α=β=γ=90 °; The same respectively Cu of N on each part benzoglyoxaline ring
4I
4A Cu coordination.Detailed axonometry data see Table 1; The match crystal body structure is seen Fig. 1.
Table 1
2) fluorescent characteristic:
The exsiccant title complex carries out fluorometric investigation after milled processed.Title complex excites at 398nm, 406nm place, all obtains emission peak at 439nm, 446nm place.See Fig. 2.
Claims (5)
1. benzimidazolyl-acridine ligand CuI complex, it is characterized in that: for benzimidazole and acridine ring are introduced the CuI part jointly and constructed the title complex of formation, this title complex can be used following chemical formulation: Cu
4I
4L
4, wherein L is a 1-benzimidazolyl-9-acridine, the molecular formula of L is:
2. the preparation method of benzimidazolyl-acridine ligand CuI complex according to claim 1 is characterized in that step is as follows:: 1) at room temperature, 1-benzimidazolyl-9-acridine is dissolved in CHCl
3In, obtain CHCl
3Solution also places the test tube bottom to constitute lower floor; 2) in this test tube, add CHCl
3/ CH
3The CN mixing solutions constitutes the middle layer; 3) CH of adding CuI in this test tube
3The CN saturated solution constitutes the upper strata; 4) leave standstill diffusion 30-35 days, can obtain the orange bulk-shaped monocrystal; 5) with monocrystalline CHCl
3The washing after drying can make.
3. the preparation method of benzimidazolyl-acridine ligand CuI complex according to claim 2, it is characterized in that: 1-benzimidazolyl-9-acridine is dissolved in CHCl
3Strength of solution be 0.01～0.02molL
-1
4. the preparation method of benzimidazolyl-acridine ligand CuI complex according to claim 2 is characterized in that: described CHCl
3/ CH
3CN mixed liquor volume ratio is 1: 1～1.5.
5. the preparation method of benzimidazolyl-acridine ligand CuI complex according to claim 2, it is characterized in that: the volume ratio of upper, middle and lower-ranking solution is 1: 6～8: 1 in the described test tube.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102127100A (en) * | 2010-01-14 | 2011-07-20 | 郑州轻工业学院 | Cadmium complex of 1,5-di(1-H-benzimidazolyl)pentane, and preparation method and application thereof |
| CN102718771A (en) * | 2012-01-12 | 2012-10-10 | 南开大学 | Indolocarbazole-based fluorescence probe and its preparation method and use |
| CN104861962A (en) * | 2015-05-21 | 2015-08-26 | 中国计量学院 | Cu4I4 cubane-like cluster core complex luminous material based on phosphine ligand |
| CN106519255A (en) * | 2016-11-05 | 2017-03-22 | 河南中医药大学 | Imidazolecarboxylic acid complex and synthesis method and application thereof |
-
2008
- 2008-11-17 CN CNA200810153106XA patent/CN101402645A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102127100A (en) * | 2010-01-14 | 2011-07-20 | 郑州轻工业学院 | Cadmium complex of 1,5-di(1-H-benzimidazolyl)pentane, and preparation method and application thereof |
| CN102127100B (en) * | 2010-01-14 | 2013-07-03 | 郑州轻工业学院 | Cadmium complex of 1,5-di(1-H-benzimidazolyl)pentane, and preparation method and application thereof |
| CN102718771A (en) * | 2012-01-12 | 2012-10-10 | 南开大学 | Indolocarbazole-based fluorescence probe and its preparation method and use |
| CN102718771B (en) * | 2012-01-12 | 2014-04-02 | 南开大学 | Indolocarbazole-based fluorescence probe and preparation method and use thereof |
| CN104861962A (en) * | 2015-05-21 | 2015-08-26 | 中国计量学院 | Cu4I4 cubane-like cluster core complex luminous material based on phosphine ligand |
| CN104861962B (en) * | 2015-05-21 | 2016-11-16 | 中国计量学院 | A kind of Cu4I4 class cubane bunch core complex luminescent material based on Phosphine ligands |
| CN106519255A (en) * | 2016-11-05 | 2017-03-22 | 河南中医药大学 | Imidazolecarboxylic acid complex and synthesis method and application thereof |
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Open date: 20090408 |