CN108373449A - A kind of structure and preparation method thereof of cyanoimidazole perchlorate - Google Patents
A kind of structure and preparation method thereof of cyanoimidazole perchlorate Download PDFInfo
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- CN108373449A CN108373449A CN201810118196.2A CN201810118196A CN108373449A CN 108373449 A CN108373449 A CN 108373449A CN 201810118196 A CN201810118196 A CN 201810118196A CN 108373449 A CN108373449 A CN 108373449A
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- Prior art keywords
- perchlorate
- cyanoimidazole
- imidazoles
- cyanophenyl
- preparation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
Abstract
The present invention provides a kind of structure and preparation method thereof of cyanoimidazole perchlorate, molecular formula C11H10N3ClO4.The preparation of the compound, which is the in the mixed solvent formed in first alcohol and water, makes a certain proportion of imidazoles cyanophenyl and perchloric acid mix, it is put into and is placed in the polytetrafluoroethylene (PTFE) of 15mL in baking oven with 30 150 DEG C of temperature heating 5 for 24 hours, white needle-like crystals are obtained after cold filtration.Method therefor operation of the present invention is succinct, safe；Its product has many advantages, such as that stability is good, crystallinity is high.There is potential application prospect in terms of the compound fluorescence.
Description
Technical field
The invention belongs to organic compound field, it is related to structure and its preparation side of a kind of cyanoimidazole perchlorate
Method.
Background technology
Nineteen forties can be traced back to by the research history in activated centre of imidazoles parent nucleus, pharmacy man at that time
Woolley speculates that imidazoles can play function similar with some bioactivity that purine causes.Between subsequent several years, largely
The multiple biological activities that medical science authoritative expert discloses imidazoles by constantly research such as inhibit oxidation, inhibit blood clotting, is anti-
Diabetes etc.；By the optimization to different loci on imidazoles parent nucleus, many good effects have also been obtained and still in the drug used
Such as mebendazol.Currently, for new types of therapeutic agents development for, design using imidazoles parent nucleus as the structure in activated centre
Through as a kind of important development approach.Imidazole and its derivants have good bioactivity, receive all the time chemistry and
The favor of pharmaceutical field research worker.Many drugs are imdazole derivatives or its complex.Have the study found that imidazoles is one
The nitrogen heterocyclic of interest, it has there are one the nitrogen-atoms comprising lone pair electrons, can be bonded a proton and form protonation sun
Ion, and because containing there are two nitrogen-atoms, be it is a kind of can in organism enzyme and receptor etc. form the spy of hydrogen bond
Different structure plays a role in anticancer, antimycotic, easing pain and diminishing inflammation etc..
Imidazoles cyanophenyl is an important pharmaceutical intermediate.However, up to the present, the synthesis of imidazoles cyanophenyl perchlorate
And crystal structure does not have document report.The present invention for this problem propose a kind of imidazoles cyanophenyl perchlorate preparation method and its
Structural characterization.
Invention content
The present invention provides a kind of structures and preparation method thereof of cyanoimidazole perchlorate.
The technical problems to be solved by the invention are achieved by the following technical programs：A kind of cyanoimidazole perchlorate
Compound, molecular formula are：C11H10N3ClO4.The mixture is monoclinic system,P21/cSpace group, cell parameter area=
8.3725 (2),b=22.5781 (5),c=7.2008 (2),α=90o,β=114.656 (4) o,γ=90o,V=1237.10(7)
Å3。
A kind of preparation method of cyanoimidazole perchlorate is：By a certain proportion of imidazoles cyanophenyl, perchloric acid be dissolved in water and
In the mixed solution of methanol, it is placed in polytetrafluoroethylene (PTFE).5-24h is heated at a temperature of 50 DEG C -150 DEG C, it is natural at room temperature
Cooling crystallizes, until white needle-like crystals are precipitated..
Beneficial effects of the present invention：The cyanoimidazole perchlorate of the present invention is conducive under hydrothermal synthesizing condition
Few defect is grown, is orientated, sample purity is high, and preparation method is simple, pollution-free.The compound has very in terms of fluorescence
Good potential application prospect.
Description of the drawings
Fig. 1, a kind of environment map of cyanoimidazole perchlorate of the present invention.
Fig. 2, a kind of one-dimensional chain figure of cyanoimidazole perchlorate of the present invention.
Fig. 3, a kind of two-dimensional structure figure of cyanoimidazole perchlorate of the present invention.
Fig. 4, a kind of accumulation graph of cyanoimidazole perchlorate of the present invention.
Specific implementation mode
With reference to embodiment, the present invention will be described in detail, and embodiment is only the preferred embodiment of the present invention,
It is not limitation of the invention.
Embodiment 1
By 0.0183g imidazoles cyanophenyls（0.1mmol）, 0.0100g perchloric acid（0.1mmol）It is dissolved in water（3ml）And methanol（3ml）'s
In mixed solution.Reaction solution is transferred in polytetrafluoroethylene (PTFE), is heated at a temperature of 100 DEG C for 24 hours, cooling, filtering, knot
It is brilliant, until white needle-like crystals are precipitated.
Above-mentioned cyanoimidazole perchlorate is characterized.
Crystal X-ray diffraction data is measured using Bruker Smart CCD single crystal diffractometers.MoKa radiation (λ=0
.71073), graphite monochromator, withωScan mode collects data, and carries out Lp factor corrections and empirical absorption correction.First
The position that other non-hydrogen atoms of metallic atom and part are determined with direct method, is then found out with difference function method and least square method
Remaining whole non-hydrogen atom coordinate, is used in combination theoretical hydrogenation method to obtain hydrogen atom position or found from difference Fourier figure, with complete
Matrix least square method is modified structure.
Fig. 1 is the environment map obtained by single crystal diffraction method.From figure 1 it appears that the compound is monoclinic system,P21/cSpace group, cell parameter area=8.3725 (2),b=22.5781 (5),c=7.2008 (2),α=90o,β=114.656
(4) o,γ=90o,V=1237.10(7)Å3.The asymmetric cell of the compound includes a perchlorate anion, a miaow
Azoles cyanophenyl cation.Wherein Cl-O keys bond distance range is 1.4336 (16) -1.4469 (15), and N-C key bond distance's ranges are 1.149
(2) -1.461 (2), C-C key bond distance's ranges are 1.348 (3) -1.399 (3).
Fig. 2 is the one-dimensional chain figure of cyanoimidazole perchlorate of the present invention.It is formed by two kinds of hydrogen bond
One-dimensional catenary structure, respectively N (1)-H (1) O (1), N (1)-H (1) N (3) bond distances and bond angle are respectively 2.9314
(19) 121 (3) ° and 2.915 (2) 138 (3) °.
Fig. 3 is the two-dimensional structure figure of cyanoimidazole perchlorate of the present invention.As shown in figure 3, by increasing C (1)-
H(1A)∙∙∙O(1)（Bond distance 3.303 (2), 141 ° of bond angle）Hydrogen bond action makes one-dimensional chain extend to two-dimentional supramolecular structure.
Fig. 4 is the accumulation graph of cyanoimidazole perchlorate of the present invention.There is also such as other than there are above-mentioned hydrogen bond
Lower hydrogen bond：C (2)-H (2) O (4), C (4)-H (4A) O (3), C (4)-H (4B) O (2), C (4)-H (4B) O
(4), its bond distance's bond angle of C (7)-H (7) O (3), C (10)-H (10) N (2) is respectively 150 ° of 3.325 (2)；3.345
(2)Å 158°；3.320(2)Å 144°；3.444(2)Å 159°；3.405(3)Å 149°；2.891(2)Å 101°；These are super
Molecular force makes two-dimensional layer extend to Magnetic Properties of Three-Dimensional Supramolecular Complex structure.
The compound of the present invention solid state fluorescence spectrum shows that its fluorescence emission peak is 414 nm.
Embodiments of the present invention above described embodiment only expresses, the description thereof is more specific and detailed, but can not
Therefore it is interpreted as the limitation to the scope of the claims of the present invention, as long as skill obtained in the form of equivalent substitutions or equivalent transformations
Art scheme should all be fallen within the scope and spirit of the invention.
Claims (4)
1. a kind of cyanoimidazole perchlorate, it is characterised in that its molecular formula is C11H10N3ClO4。
2. the compound is monoclinic system,P21/cSpace group, cell parameter area=8.3725 (2),b=22.5781 (5),c=
7.2008 (2),α=90o,β=114.656 (4) o,γ=90o,V=1237.10(7)Å3, the asymmetric cell of the compound includes
One perchlorate anion, an imidazoles cyanophenyl cation, wherein Cl-O keys bond distance range is 1.4336 (16) -1.4469
(15), N-C keys bond distance range is 1.149 (2) -1.461 (2), and C-C key bond distance's ranges are 1.348 (3) -1.399 (3).
3. the preparation method of cyanoimidazole perchlorate according to claim 1, which is characterized in that include the following steps：
It is 0.8 ~ 1.2 by molar ratio:0.8 ~ 1.2 imidazoles cyanophenyl, perchloric acid are mixed to join in the mixed solvent of first alcohol and water composition,
Be placed in polytetrafluoroethylene (PTFE) solvent and 5-24h heated with 50 DEG C -150 DEG C of temperature, at room temperature natural cooling, crystallization, until analysing
Go out white needle-like crystals.
4. the application of cyanoimidazole perchlorate according to claim 1, it is characterised in that the salt based on imidazoles cyanophenyl
It can be used as effective fluorescent material.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810118196.2A CN108373449A (en) | 2018-02-06 | 2018-02-06 | A kind of structure and preparation method thereof of cyanoimidazole perchlorate |
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| CN201810118196.2A CN108373449A (en) | 2018-02-06 | 2018-02-06 | A kind of structure and preparation method thereof of cyanoimidazole perchlorate |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| CN107434787A (en) * | 2017-07-25 | 2017-12-05 | 齐鲁工业大学 | A kind of preparation, structure and the photoluminescent property of benzimidazole perchlorate |
-
2018
- 2018-02-06 CN CN201810118196.2A patent/CN108373449A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| CN107434787A (en) * | 2017-07-25 | 2017-12-05 | 齐鲁工业大学 | A kind of preparation, structure and the photoluminescent property of benzimidazole perchlorate |
Non-Patent Citations (1)
| Title |
|---|
| YAN-HONG XU ET AL.: "Self-assembly of zinc polymers based on a flexible linear ligand at different pH values: Syntheses, structures and fluorescent properties", 《SOLID STATE SCIENCES》 * |
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