CN104193684A - 4-aminophenazone 2,5-dihydroxy benzaldehyde Schiff base and application thereof - Google Patents

4-aminophenazone 2,5-dihydroxy benzaldehyde Schiff base and application thereof Download PDF

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CN104193684A
CN104193684A CN201410417953.8A CN201410417953A CN104193684A CN 104193684 A CN104193684 A CN 104193684A CN 201410417953 A CN201410417953 A CN 201410417953A CN 104193684 A CN104193684 A CN 104193684A
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dihydroxy benzaldehyde
base
contracting
benzaldehyde schiff
schiff
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CN104193684B (en
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刘峥
李巍
魏席
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Guilin University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
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    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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

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Abstract

The invention discloses 4-aminophenazone 2,5-dihydroxy benzaldehyde Schiff base and application thereof. 4-aminophenazone 2,5-dihydroxy benzaldehyde Schiff base has a molecular formula of C18H17N3O3, the molecular weight of 323.35 and the melting point of 299-301 DEG C. A preparation method of 4-aminophenazone 2,5-dihydroxy benzaldehyde Schiff base comprises the following steps: (1) completely dissolving 0.61g of 2,5-dihydroxy benzaldehyde in 10mL of absolute methanol, transferring to a three-mouth flask, and magnetically stirring in a water bath at 35 DEG C; (2) dissolving 1.0162g of 4-aminophenazone in 10mL of absolute methanol, and ultrasonically dissolving; (3) slowly dropwise adding a solution obtained in the step (2) into a solution obtained in the step (1); refluxing at 60 DEG C for 4 hours under the magnetic stirring condition, cooling, filtering, standing filter liquor at the room temperature for a week to generate yellow brown crystals, filtering, and airing to obtain 4-aminophenazone 2,5-dihydroxy benzaldehyde Schiff base. 4-aminophenazone 2,5-dihydroxy benzaldehyde Schiff base can serve as a fluorescent probe to be applied in the field of fluorescent analysis.

Description

4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base and application
Technical field
The present invention relates to the synthetic of 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base, described Schiff's base crystal has laminate structure, and its stronger photoluminescent property makes it can be used as fluorescent probe to be applied at analysis field.
Background technology
Schiff's base refers to and contains the class organic compound containing C=N base that active carbonyl and two amino class materials form by condensation reaction.At home, start late about the synthetic work of Schiff's base, but development is very fast.In recent years, existing lot of documents is reported relevant Schiff's base and title complex thereof.Along with deepening continuously of Schiff's base and metal complexes research thereof, it is found that it has good fluorescent characteristic, can be used as fluorescent molecular probe and role in fluorescent molecule switch, be applied to analytical chemistry and biochemical field.Generally, " rigidity, plane, large conjugation ∏ key " is the constitutional features of fluorescent chemicals, and the synthetic schiff base compounds with fluorescent characteristics structure is a research work highly significant targetedly.4-AA Schiff's base has following obvious feature: the C=N that the aromatic nucleus in (1) 4-AA molecular structure can increase molecular conjugation system and Schiff's base has again the electronic bridge of mobility, can strengthen fluorescent emission, large conjugated system plays important effect making low-dimensional molecule form the more Supramolecular Network structure of higher-dimension in addition, so 4-AA Schiff's base can become the fluorescent reagent of excellent property; (2) from the angle of weak interaction and molecular geometry, the existence of aromatic nucleus is also in network and internetwork π ... the formation of pi accumulation provides more convenient condition, this is also conducive to the formation of Supramolecular Network structure, thereby affect the character of fluorescence, therefore 4-AA Schiff's base is synthetic, and the application and development of compounds in fluorometric analysis field provides possibility for this reason.4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base is a kind of new 4-AA Schiff's base, its crystalline structure has no report, the present invention proposes a kind of 4-AA contracting 2 with laminate structure, the synthetic method of 5-Dihydroxy benzaldehyde Schiff's base, for further studying 4-AA contracting 2,5-Dihydroxy benzaldehyde schiff base structure and providing basic data with the relation of photoluminescent property.
Summary of the invention
Object of the present invention is exactly to synthesize 4-AA contracting 2, the 5-Dihydroxy benzaldehyde Schiff's base with laminate structure, makes it have stronger photoluminescent property, and can be applied at analysis field as fluorescent probe.
4-AA contracting 2, the 5-Dihydroxy benzaldehyde Schiff's base molecular formula the present invention relates to is C 18h 17n 3o 3, molecular weight is 323.35, and fusing point is 299 DEG C-301 DEG C, and its crystallographic data is in table 1, and bond distance and bond angle are in table 2.
The crystallographic data of table 14-aminoantipyrene contracting 2,5-Dihydroxy benzaldehyde Schiff's base
Note: w=1/[σ 2(Fo 2)+(0.060P) 2+ 5.787P], P=(Fo 2+ 2Fc 2)/3
The bond distance of table 24-aminoantipyrene contracting 2,5-Dihydroxy benzaldehyde Schiff's base and bond angle (°)
The concrete steps of the synthetic method of 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base are:
(1) take 0.61g 2,5-Dihydroxy benzaldehyde is dissolved in 10mL anhydrous methanol, after dissolving completely, is transferred in there-necked flask, stirs at 35 DEG C of water bath condition lower magnetic forces.
(2) take 1.0162g 4-AA and be dissolved in 10mL anhydrous methanol, ultrasonic dissolution.
(3) step (2) gained solution is slowly added drop-wise in step (1) gained solution; Under 60 DEG C of magnetic agitation conditions, reflux 4 hours, cooling, filtration, filtrate at room temperature leave standstill has tawny crystal to generate after one week, filter, and obtains 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base (C after drying 18h 17n 3o 3).
4-AA contracting 2,5-Dihydroxy benzaldehyde can be applied in fluorometric analysis field as fluorescent probe.
Brief description of the drawings
Fig. 1 is 4-AA contracting 2, the 5-Dihydroxy benzaldehyde Schiff's base crystalline structure figure that the embodiment of the present invention makes.
Fig. 2 is the three-dimensional accumulation graph of 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base crystal that the embodiment of the present invention makes.
Fig. 3 is 4-AA contracting 2, the 5-Dihydroxy benzaldehyde Schiff's base DMF solution fluorescence spectrum figure that the embodiment of the present invention makes.
Embodiment
Embodiment:
The concrete steps of the synthetic method of 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base are:
(1) take 0.61g 2,5-Dihydroxy benzaldehyde is dissolved in 10mL anhydrous methanol, after dissolving completely, is transferred in there-necked flask, stirs at 35 DEG C of water bath condition lower magnetic forces.
(2) take 1.0162g 4-AA and be dissolved in 10mL anhydrous methanol, ultrasonic dissolution.
(3) step (2) gained solution is slowly added drop-wise in step (1) gained solution; Under 60 DEG C of magnetic agitation conditions, reflux 4 hours, cooling, filtration, filtrate at room temperature leave standstill has tawny crystal to generate after one week, filter, and obtains 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base (C after drying 18h 17n 3o 3).
The 4-AA contracting 2 making, 5-Dihydroxy benzaldehyde Schiff's base crystal structure analysis: choose the 4-AA contracting 2 that is of a size of 0.35 × 0.33 × 0.32mm, 5-Dihydroxy benzaldehyde Schiff's base tawny monocrystalline is arranged on glass fibre, visit diffractometer at Bruker Smart CCD type X-ray diffraction analyser face and carry out crystal structure determination, under 298 (2) K, adopt graphited Mo K alpha-ray within the scope of 3.9≤θ≤28.7 °, collect altogether 8046 point diffractions with ω scan mode, wherein 3184 independent point diffractions, the Observable point diffraction of 2597 I>2 σ (I) is for structural analysis and structural modifications.All data is through the Lp factor and experience absorption correction, and crystalline structure is solved by direct method, and whole non-hydrogen atoms and anisotropy thermal parameter thereof are carried out to complete matrix least-squares refinement, and hydrogen atom is provided by theoretical value.All calculating is used SHELXS97, SHELXL97 program to complete.
Known from crystallographic parameters and the structure refinement parameter (table 1) of 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base, 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base belongs to oblique system, and spacer is P2 1/ n, unit cell parameters is a=7.5411 (3), b=7.4350 (4), c=27.9267 (11), α=90.00, β=97.687 (6), γ=90.00, V=1557.62 (12).Found out by Fig. 1 and Fig. 2,4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base crystal molecule structure is linear chiral molecular, in this structure, hydroxyl and phenyl ring and adjacent carbon atom form π-pi-conjugated two dimensional structure that is, and imino-and pyrazolone be not in two dimensional structure.Can find out from three-dimensional accumulation graph, Schiff's base is taking the overlapping phenyl ring of two molecular cells as axis, phenyl ring on 4-AA is parallel to each other, the stacked direction of axis both sides is contrary, and cross arrangement forms a undaform pattern, may be electrostatic attraction between layers, Van der Waals force, under the acting in conjunction of intermolecular weak force, cross arrangement, is stacked to three-dimensional structure.
4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base Infrared spectroscopy: the stretching vibration absorption peak of C=N is 1652.34cm -1, at 3398.58cm -1position should be the stretching vibration absorption peak of phenolic hydroxyl group O-H key, and the skeletal vibration absorption peak of phenyl ring is positioned at 1590.59cm -1, 1492.79cm -1and 1459.90cm -1place, proves that phenyl exists, 1400.27cm -1and 1384.84cm -1for CH 3flexural vibration peak, 1590.59cm -1the absorption peak at place can be attributed to the stretching vibration peak of ketone C=O.Known 4-AA contracting 2 from ultraviolet spectrogram, there are 3 obvious absorption peaks in 5-Dihydroxy benzaldehyde Schiff's base, the absorption peak that 264nm place occurs, judge according to molecular structure, can be attributed to π～π * transition of the C=N generation of conjugation, the absorption peak at 337nm place can be attributed to n～π * transition of two phenol O-H, and is n～π * transition of pyrazole ring carbonyl at the sharp-pointed absorption peak at 375nm place.
4-AA contracting 2,5-Dihydroxy benzaldehyde is applied in fluorometric analysis field as fluorescent probe.

Claims (2)

1. 4-AA contracting 2, a 5-Dihydroxy benzaldehyde Schiff's base, is characterized in that the molecular formula of 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base is C 18h 17n 3o 3, molecular weight is 323.35, and fusing point is 299 DEG C-301 DEG C, and its crystallographic data is in table 1, and bond distance and bond angle are in table 2;
The crystallographic data of table 1:4-aminoantipyrene contracting 2,5-Dihydroxy benzaldehyde Schiff's base
Note: w=1/[σ 2(Fo 2)+(0.060P) 2+ 5.787P], P=(Fo 2+ 2Fc 2)/3
The bond distance of table 2:4-aminoantipyrene contracting 2,5-Dihydroxy benzaldehyde Schiff's base and bond angle (°)
The synthetic method of described 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base is:
(1) take 0.61g 2,5-Dihydroxy benzaldehyde is dissolved in 10mL anhydrous methanol, after dissolving completely, is transferred in there-necked flask, stirs at 35 DEG C of water bath condition lower magnetic forces;
(2) take 1.0162g 4-AA and be dissolved in 10mL anhydrous methanol, ultrasonic dissolution;
(3) step (2) gained solution is slowly added drop-wise in step (1) gained solution; Under 60 DEG C of magnetic agitation conditions, reflux 4 hours, cooling, filtration, filtrate at room temperature leave standstill has tawny crystal to generate after one week, filter, and after drying, obtaining 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base is C 18h 17n 3o 3.
2. the application of 4-AA contracting according to claim 12,5-Dihydroxy benzaldehyde Schiff's base, is characterized in that 4-AA contracting 2,5-Dihydroxy benzaldehyde Schiff's base can be applied in fluorometric analysis field as fluorescent probe.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109776404A (en) * 2017-11-13 2019-05-21 中国科学院大连化学物理研究所 A kind of synthetic method of dimerization (heteroaromatic) azo phenylate fluorescent molecule

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WO2012041524A1 (en) * 2010-10-01 2012-04-05 Max-Delbrück-Centrum Für Molekulare Medizin (Mdc) Hydrazonopyrazolones as protein tyrosine phosphatase inhibitors
WO2013072921A2 (en) * 2011-09-13 2013-05-23 Glenmark Generics Limited Process for preparation of substituted 3'-hydrazino-biphenyl-3-carboxylic acid compounds
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WO2012041524A1 (en) * 2010-10-01 2012-04-05 Max-Delbrück-Centrum Für Molekulare Medizin (Mdc) Hydrazonopyrazolones as protein tyrosine phosphatase inhibitors
WO2013072921A2 (en) * 2011-09-13 2013-05-23 Glenmark Generics Limited Process for preparation of substituted 3'-hydrazino-biphenyl-3-carboxylic acid compounds
CN103980252A (en) * 2014-05-30 2014-08-13 遵义医学院 1, 2, 4-triazole-contained triazole Schiff base drug for treating tumor

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109776404A (en) * 2017-11-13 2019-05-21 中国科学院大连化学物理研究所 A kind of synthetic method of dimerization (heteroaromatic) azo phenylate fluorescent molecule
CN109776404B (en) * 2017-11-13 2022-07-15 中国科学院大连化学物理研究所 Synthesis method of dimeric (aromatic heterocyclic) azobenzene ether fluorescent molecule

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