CN104844636A - High-temperature hydrothermal synthesis and application based on bromopyridine-triazole Cd(II) complex - Google Patents

High-temperature hydrothermal synthesis and application based on bromopyridine-triazole Cd(II) complex Download PDF

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CN104844636A
CN104844636A CN201510203301.9A CN201510203301A CN104844636A CN 104844636 A CN104844636 A CN 104844636A CN 201510203301 A CN201510203301 A CN 201510203301A CN 104844636 A CN104844636 A CN 104844636A
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triazole
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bromopyridine
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丁斌
武向侠
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Tianjin Normal University
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    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/08—Cadmium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract

The invention discloses high-temperature hydrothermal synthesis and application based on bromopyridine-triazole Cd(II) complex. The triazole Cd(II) complex having a chain-type framework structure is mainly applied to the aspect of molecule-based optical materials. 4-(5-bromopyridine)-1,2,4-triazole ligand is not seen and reported in any literature, and the triazole Cd(II) complex based on the 4-(5-bromopyridine)-1,2,4-triazole ligand is the first case. Test results show that the triazole Cd(II) complex can emit strong blue-light emission spectrum, and has a wide application prospect in the aspect of molecule-based optical materials.

Description

Based on high-temperature water thermal synthesis and the application of pyridine bromide-triazole Cd (II) title complex
Statement about subsidizing research or exploitation: the present invention carries out under the subsidy of Tianjin application foundation and cutting edge technology research plan Tianjin Nsfc Projects (Grant no. 14JCQNJC05900) and project of national nature science fund project (Grant No. 21301128).
Technical field
The invention belongs to organic water thermal synthesis and Organometallic Chemistry technical field, relate to the synthesis of 4-(5-bromopyridine)-1,2, the 4-triazole ligand having no bibliographical information and there is the Cd(NCS of fluorescence property) 2the Hydrothermal Synthesis of-L title complex, be in particular based on 4-(5-bromopyridine)-1,2,4-triazole ligand (L) triazole Cd ( ) fluorescence complex Hydrothermal Synthesis and in the application in molecular based optical material.
Background technology
Some inorganic fluorescent materials, such as BaMgAl 10o 17: Eu 2+and GdMgB 5o 10: Ce 3+, Tb 3+, be used for commercial use as blue and green fluorescence lamp source.The optical property of their uniquenesses gives the credit to rare earth ion and forms narrower fluorescence emission peak and high pure colorimetric.Research shows, atomic structure, the homogeneity of formation, size of particles, textural defect, and particle microtexture and interface composition all can affect the fluorescent characteristic of inorganic fluorescent material.Wherein the most typically the fluorescence property of CdS nanoparticle can change with size of particles.It is found that by change particle size title complex just can be made to carry out the transformation of green glow and ruddiness.Organic fluorescence materials is then mainly used in OLEDs (organic electroluminescent light diode) aspect.
The metal center of fluorescence complex, organic moiety, metal-organic charge transition, the guest molecule in porous coordination compound all may cause luminescence.Known by people due to their potential application in fluorescent optical sensor, nonlinear optics, photic catalysis, display, photodiode, biological medicine image applications.People's extensive concern they in environment and biosystem as the practical application of chemical sensor, utilized simultaneously the fluorescence of this kind of title complex, nano level operability and stable porous performance start to explore it at tissue and cell imaging, the application of drug testing and treatment aspect.
The luminosity of coordination compound is very responsive, depends on their constructional feature, metallic ion coordination environment, the character of pore surface and being interacted by coordinate bond, hydrogen bond and pi-pi bond and guest molecule.The permanent hole of some porous emitting complexes can carry out reversible absorption and the release of part transducer, thus makes the coordination compound of exploration reversible fluorescence sensing become feasible.Adjustable pore dimension is for the selective recognition of small molecules, ion, offunctional site as Lewis base/sour site and in title complex the interaction of open metallic site and guest molecule really will strengthen the sensing sensitivity of title complex, and the mesoporous characteristic of mesoporous emitting complexes will make some macromole sensing such as bioactive species become possibility.
In recent years, Metal-organic complex because of it possess Stability Analysis of Structures, specific surface area is large, duct volume large and the fluorescent characteristic of self, have a wide range of applications in illumination, display, object sensing and optical device etc., Chang Zuowei luminescent material such as photodiode (LEDs) is applied, and the fluorescent characteristic research of title complex becomes a focus of MOFs research.As everyone knows, the character of any material depends primarily on their structure.How the title complex of directed Hydrothermal Synthesis expected structure is all a challenging job all the time.The luminescent properties of functional complexes not only forms relevant with material, and depend on the molecular structure of title complex and intramolecular accumulation mode to a great extent, so the accumulation mode controlling the three-dimensional structure of title complex and title complex is on a molecular scale all extremely important.
Hydrothermal Synthesis refers to that temperature is 100 ~ 1000 DEG C, pressure reacts for utilizing matter chemistry in the aqueous solution under 1MPa ~ 1GPa condition the Hydrothermal Synthesis carried out.Subcritical with under supercritical water heat condition, because reaction is in molecular level, reactive raising, thus hydro-thermal reaction can substitute some high temperature solid state reaction.Again due to the homogeneous nucleation of hydro-thermal reaction and nonhomogen-ous nucleation mechanism different from the flooding mechanism of solid state reaction, thus can create new compound and novel material that other method cannot be prepared.Its advantage: product purity high, good dispersity, granularity are easy to control.
The invention belongs to organic water thermal synthesis and Organometallic Chemistry technical field, relate to there is chain skeleton construction triazole Cd ( ) Hydrothermal Synthesis of title complex, be in particular 4-(5-bromopyridine)-1,2,4-triazole ligand triazole Cd ( ) title complex hydro-thermal Hydrothermal Synthesis and apply as optical material.Triazole Cd (II) title complex with chain skeleton construction of the present invention is mainly used in molecular based optical material aspect.4-(5-bromopyridine)-1,2,4-triazole ligand has no bibliographical information, this is that first case is based on 4-(5-bromopyridine)-1,2, triazole Cd (II) title complex of 4-triazole ligand, test-results shows: this triazole Cd (II) title complex can launch strong blue emission spectrum, and particularly there is a wide application prospect molecular based optical material aspect.This triazole Cd (II) title complex develops the development to advanced material or the theoretical investigation to microphysics all has great importance.
Summary of the invention
One object of the present invention discloses { [Cd (H 2o) (NCS)] (L) } (1) compound.
The preparation method of another object of the present invention discloses (1) compound crystal, the research of take off data and data.
Further object of the present invention disclose there is chain skeleton construction triazole Cd ( ) preparation of title complex.
Further object of the present invention discloses { [Cd (H 2o) (NCS)] (L) } (1) compound has the title complex of chain skeleton construction in molecular based optical material, particularly blue-fluorescence source material aspect.Owing to having metal center, organic moiety, metal-organic charge transition, the guest molecule in porous coordination compound all may cause luminescence.Known by people due to their potential application in fluorescent optical sensor, nonlinear optics, photic catalysis, display, photodiode, biological medicine image applications.
For achieving the above object, the invention provides following technical scheme:
Have chain skeleton construction triazole Cd ( ) title complex, this compound is new, does not have this material of bibliographical information by scifinder inquiry; Its chemical general formula is as follows:
{[Cd(H 2O)(NCS)](L)} （1）；
The L structural formula having no bibliographical information is
L refers to 4-(5-bromopyridine)-1,2,4-triazole ligand, is not had the bibliographical information of ligand L by scifinder inquiry.
The present invention further discloses there is chain skeleton construction triazole Cd ( ) complex monocrystal, the BRUKER SMART 1000 X-ray single crystal diffraction instrument of oblique system wherein, adopts the Mo of graphite monochromator kα radiation (λ=0.071 073 nm) as diffraction light sources, at 173 (2) K temperature, with scan mode, measures predominant crystal data as follows:
The present invention further discloses there is chain skeleton construction triazole Cd ( ) title complex method, it is characterized in that: take 0.0637 g (0.5 mmol) Cd(NCS) 2by 5 mL water dissolution, take ligand L 0.106 g(0.5 mmol) use 5mL dissolve with ethanol, by above two kinds of solution mixing, be then put in the water heating kettle of 15 mL and keep three days at 120 DEG C, after slow cooling, obtain colourless transparent crystal.
The present invention further disclose there is chain skeleton construction triazole Cd ( ) title complex { [Cd (H 2o) (NCS)] (L) } ( 1), this triazole Cd ( ) title complex can launch strong blue emission spectrum, particularly there is a wide application prospect molecular based optical material aspect.
Accompanying drawing illustrates:
Fig. 1 be triazole Cd ( ) molecular structure of title complex;
Fig. 2 be triazole Cd ( ) the chain-like structure figure of title complex;
Fig. 3 triazole Cd ( ) title complex Solid fluorescene spectrum figure (Solid fluorescene spectrum wavelength is within the scope of 450-490 nm blue-light source).
Embodiment
In order to simple and clearly object, the hereafter appropriate description eliminating known technology, in order to avoid the description of those unnecessary details impact to the technical program.Below in conjunction with preferred embodiment, the present invention will be further described, is illustrated especially, prepares the initial substance Cd(NCS of the compounds of this invention) 2, the bromo-PA of 5-, two formyl hydrazine, benzene, ethanol can commercially or easily be obtained (reagent prepared used by the compounds of this invention all derives from business and buys, and rank is analytical pure) by known method.
Need in addition to be illustrated: all experimental implementation use Schlenk technology, and solvent is through normal process purifying.All reagent for Hydrothermal Synthesis and analysis is all analytical pure, not through further process.Fusing point is measured by Boetius block apparatus. 1h NMR composes by mercury variable V x300 spectrophotometer record, surveying range: 300 MHz.Chemical shift, δ, the TMS with reference to international standard measures.
Embodiment 1
Reference example 1
The L structural formula having no bibliographical information is
L refers to 4-(5-bromopyridine)-1,2,4-triazole ligand.
Preparation method: the bromo-PA of 5-of 2.2 g, with two formyl hydrazine mixing of 4.0 g, is heated to 165 oc, at 185-190 oreact 30 minutes under C, after benzene and ethanol difference recrystallization, obtain the ligand L of white needles.Prepare document: J. Org. Chem. 1953,18,1368.
Preparation embodiment 1
120 ° of C Hydrothermal Synthesiss of title complex (1)
Take 0.0637 g (0.5 mmol) Cd(NCS) 2by 5 mL water dissolution, take ligand L 0.106 g(0.5 mmol) use 5mL dissolve with ethanol, by above two kinds of solution mixing, be then put in the water heating kettle of 15 mL and keep three days under 120 ° of C, after slow cooling, obtain colourless transparent crystal.
Results of elemental analyses, experimental value (%): C, 26.99%; H, 2.45%; N, 19.86%.;
According to C 16h 16cdI 2n 8the theoretical value (%) calculated: C, 26.8128%; H, 2.2501%; N, 19.5430%.
FT-IR (KBr, cm -1): 3400（Br）,3100 (m), 1650 (m), 1525 (m), 1380 (m), 1310 (m), 1260 (m), 1080 (m), 930 (m), 800 (m),700(m), 630 (s), 530 (m)。
Embodiment 2
(1) structure determination of title complex
Choose the monocrystalline BRUKER SMART 1000 X-ray single crystal diffraction instrument that size is 0.14 mm × 0.10, mm × 0.13 mm, adopt the Mo of graphite monochromator kα radiation (λ=0.071 073 nm) as diffraction light sources, at 173 (2) K temperature, with scan mode, 2.74 °≤ θ≤ 29.16 ° (-10≤ h≤ 10 ,-10≤ k≤ 10 ,-14≤ l≤ 13), in scope, 4262 point diffractions, wherein 2645 independent point diffractions are collected altogether .Crystalline structure is solved by direct method, non-hydrogen atom is obtained by difference Fourier synthesis method, the method determined and revise hydrogen atom is theoretical hydrogenation, adopt isotropy and anisotropy thermal parameter to carry out complete matrix least-squares refinement to structure respectively to hydrogen atom and non-hydrogen atom, all calculating SHELXS-97 and SHELXL-97 routine package complete.The predominant crystal data of title complex list in table 1.
No. CCDC (No. CCDC is cambridge structure database numbering) of title complex 1: 1060330
the monocrystalline data of table 1 title complex 1
2 results and discussion
2.1 infrared spectra
Title complex 1iR spectrum at 3100 cm -1there is a medium tenacity absorption peak at place, and its width reaches 50 cm -1above, owing to the stretching vibration of CH in the pyridine in molecule and triazole ring, the association due to hydrogen bond makes peak broaden.Title complex 1infrared spectra at 1380 cm -1the absorption peak of left and right can be designated as the stretching vibration peak of C=N double bond, and at 630 cm -1indicate the existence of triazole ring group, title complex { [Cd (H 2o) (NCS)] (L) } ( 1) Infrared spectroscopy consistent with its crystal structure analysis result.
2.2 crystalline structure
The crystal of title complex 1 belongs to oblique system, P-1 spacer, and main bond distance and bond angle list in table 2, and its crystalline structure as shown in Figure 1.As seen from Figure 1, occur the structure (Cd1) of Liao Yige center cadmium in each complex molecule, it should be noted that part exists with the form of bridging coordination, sulphur hydracid ion is present in the lattice of title complex 1 with bridging coordination mode.For the basic structural unit of title complex 1, Cd1 respectively with from two nitrogen-atoms of four sulphur hydracid ligand moleculars and two sulphur atoms, two coordinated water molecules define hexa-coordinate CdN 2sO 2coordination configuration.Cd ( ) coordination bond lengths of ion and nitrogen-atoms is 0.2306(3) nm, these all meet bond distance's scope of bibliographical information.
Coordinated water in title complex, the nitrogen-atoms in ligand L define mutually abundant O-HN hydrogen bond.Just because of the effect of these hydrogen bonds, the sterie configuration of title complex is made to present stable Magnetic Properties of Three-Dimensional Supramolecular Complex structure.The plane that in molecule, two Benzene Molecules and triazole molecule are formed is parallel to each other, shows to there is stronger pi-pi accumulation effect between the phenyl ring gripped altogether and triazole plane.These pi-pi accumulation effects and weak interaction assemble the structure that title complex defines Magnetic Properties of Three-Dimensional Supramolecular Complex further.As shown in Figure 3, this triazole Cd ( ) title complex can launch strong blue emission spectrum, particularly there is a wide application prospect molecular based optical material aspect.This triazole Cd ( ) title complex develops the development to advanced material or the theoretical investigation to microphysics all has great importance.
The part bond distance of table 2 title complex 1 and bond angle
Embodiment 3
Cd ( ) concrete instance of title complex in molecular based optical material
The people such as Liu are by use conjugation bitooth ligand 2,8-bis [2-(2-pyridyl) vinyl]-5,11-di (2-ethylhexyl)-indolo [3,2-b] carbazole (BPVIC) and Cd coordination obtain title complex Cd 2(BPVIC) 2(SCN) 4.Under 452 nm wavelength excite, free ligand is at 477 nm place display maximum emission wavelengths; When excitation wavelength becomes 480 nm, obvious red shift to 562 nm of emission peak of this title complex, intensity obviously increases.The fluorescence retention time of title complex is 3 times of free ligand.Between title complex from part, fluorescence intensity and the different of retention time can by explaining with intermolecular electronics and space factor in molecule.Due to Cd 2+ion coordination effect, title complex forms novel π-electron system and narrow π-π * energy gaps in the delocalization environment optimized.Furthermore, owing to there is Cd (NCS) in title complex 2zig-zag chain, eliminates π-π and C-H between part ...π interacts, and decreases radiationless decay.
Reference:
1. H. J. Liu, X. T. Tao, J. X. Yang, Y. X. Yan, Y. Ren, H. P. Zhao, Q. Xin, W. T. Yu and M. H. Jiang, Cryst. Growth Des., 8, 259(2008).
Embodiment 4
Based on 4-(5-bromopyridine)-1,2,4-triazole ligand triazole Cd ( ) title complex is as the application of blue light emitting material.
Method: by MPF-4 solid fluorescence spectrophotometer, respectively to the excitation wavelength of this compound (embodiment 1) and the scanning of emission wavelength, selects and determines optimal wavelength.
Conclusion: the excitation wavelength of this title complex and emission wavelength are respectively 300 and 465 nm.
Step: will based on the triazole Cd of 4-(5-bromopyridine)-1,2,4-triazole ligand ( ) complex monocrystal grinding compressing tablet become external diameter to be 27 mm, thickness is the sheet sample of 2-3mm, and the sample pool putting into MPF-4 fluorescence spectrophotometer is measured.
Result: excitation wavelength lambda ex=300 nm of this compound, λ em=465 nm.
Conclusion:
The invention discloses based on 4-(5-bromopyridine)-1,2,4-triazole ligand triazole Cd ( ) title complex and 120 ° of C high-temperature water process for thermosynthesizing thereof and application.Of the present invention there is chain skeleton construction triazole Cd ( ) title complex is mainly used in molecular based optical material aspect.4-(5-bromopyridine)-1,2,4-triazole ligand have no bibliographical information, this be first case based on 4-(5-bromopyridine)-1,2,4-triazole ligand triazole Cd ( ) title complex, test-results shows: this triazole Cd ( ) title complex can launch strong blue emission spectrum within the scope of 450-490 nm, in molecular based optical material, particularly have the application prospect that wide.This triazole Cd ( ) title complex develops the development to advanced material or the theoretical investigation to microphysics all has great importance.

Claims (5)

1. based on pyridine bromide-triazole Cd ( ) title complex, its chemical general formula is as follows:
{ [Cd (H 2o) (NCS)] (L) } ( 1); The structural formula of L is
L refers to 4-(5-bromopyridine)-1,2,4-triazole ligand.
2. described in claim 1 based on pyridine bromide-triazole Cd ( ) complex monocrystal, the BRUKER SMART 1000 X-ray single crystal diffraction instrument of triclinic(crystalline)system wherein, adopts the Mo of graphite monochromator kα radiation (λ=0.071 073 nm) as diffraction light sources, at 172 (2) K temperature, with scan mode, measures predominant crystal data as follows:
。
3. one kind prepare described in claim 2 based on pyridine bromide-triazole Cd ( ) method of complex crystal, it is characterized in that: take 0.0637 g (0.5 mmol) Cd(NCS) 2by 5 mL water dissolution, take ligand L 0.106 g(0.5 mmol) use 5mL dissolve with ethanol, by above two kinds of solution mixing, be then put in the water heating kettle of 15 mL and keep three days at 120 DEG C, after slow cooling, obtain colourless transparent crystal.
4. described in claim 1 based on pyridine bromide-triazole Cd ( ) title complex in molecular based optical material, the particularly application of blue-fluorescence source material aspect.
5. application according to claim 4, wherein said molecular based material refers to the hybrid material structurally comprising metal center and organic ligand part, described blue-fluorescence source material refers to molecular based material and measures Solid fluorescene spectrum, the fluorescent material of its Solid fluorescene spectrum wavelength in 450-490 nm scope (blue-light source scope).
CN201510203301.9A 2015-04-27 2015-04-27 High-temperature water thermal synthesis based on pyridine bromide-triazole Cd (II) coordination compound and application Expired - Fee Related CN104844636B (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105566361A (en) * 2016-01-05 2016-05-11 天津师范大学 1,4-dibromo-2,5-dimethylene bis(triazole) cadmium complex monocrystal and applications thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DING B. ET AL: ""Synthesis of a series of 4-pyridyl-1,2,4-triazole-containing cadmium(II) luminescent complexes"", 《DALTON TRANS》, vol. 25, no. 5, 14 November 2005 (2005-11-14), pages 665 - 675 *
O. G. SHAKIROVA. ET AL: ""Synthesis and Physicochemical Study of Iron(II), Cobalt(II),Nickel(II), and Copper(II) Complexes with 4-(2-Pyridyl)-1,2,4-Triazole"", 《RUSSIAN JOURNAL OF COORDINATION CHEMISTRY》, vol. 30, no. 7, 31 December 2004 (2004-12-31), pages 507 - 513 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105566361A (en) * 2016-01-05 2016-05-11 天津师范大学 1,4-dibromo-2,5-dimethylene bis(triazole) cadmium complex monocrystal and applications thereof

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