CN112778791B - Antimony complex dye (SbDIPY) and preparation method thereof - Google Patents

Antimony complex dye (SbDIPY) and preparation method thereof Download PDF

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CN112778791B
CN112778791B CN202011533664.6A CN202011533664A CN112778791B CN 112778791 B CN112778791 B CN 112778791B CN 202011533664 A CN202011533664 A CN 202011533664A CN 112778791 B CN112778791 B CN 112778791B
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姜新东
邵竹梅
岳帅
崔天放
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Shenyang University of Chemical Technology
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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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
    • G—PHYSICS
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    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
    • G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
    • G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
    • G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract

An antimony complex dye (SbDIPY) and a preparation method thereof relate to a dye and a preparation method, and the invention provides a new class of dyeAn antimony complex dye (azadipyrrin-anti (VI): aza-SbDIPY), a method of making the same, and the efficiency of singlet oxygen production. The dye is prepared by complexing SbF with azadipyrromethene ligand for the first time 5 And the developed aza-SbDIPY is a novel series of dyes with a mother nucleus. The structural formula of the dye is shown as the formula I/II/III. The dye has the advantages of the classical traditional dye BODIPY/aza-BODIPY spectral performance and the like. The central atom Sb is hexacoordinated, and the novel aza-SbDIPY has higher extinction coefficient and long-wave absorption from visible light to near infrared region. Aza-SbDIPY can tolerate trace amounts of water and find its application in low humidity conditions. Aza-SbDIPY can be used as photosensitizer and can be applied to the generation of singlet oxygen.

Description

Antimony complex dye (SbDIPY) and preparation method thereof
Technical Field
The invention relates to a dye and a preparation method thereof, in particular to an antimony complex dye (SbDIPY) and a preparation method thereof.
Background
Azadipyrromethene (Azadipyrromethene), reported by m. Rogers in 1943, consisted of two pyrroles linked by a methine bridge. As classical bidentate ligands with BF 2 The aza-BODIPY formed by complexing the groups shows high-intensity near infrared absorption, high fluorescence quantum yield and chemical and photochemical stability. Azadipyrromethene has also been explored as a bidentate ligand for complexation with different metals (Zn, cu, co, ni, hg, etc.) to form metal dipyrrole complexes with a variety of specific properties.
The azafluoroborodipyrromethene dye is a novel fluorescent dye which is widely focused in recent years, has the characteristics of long absorption and emission wavelength, good light stability, narrow half-peak width, high quantum yield, large molar extinction coefficient and the like, and is difficult to modify molecules. Has good application prospect in the field of biological analysis and has become a hot spot for research in recent years.
The applicant has devised and disclosed a first example of PnO2-PODIPY dye, a novel dye PnO2-PODIPY/PnO2-azaPODIPY, abbreviated as PnO2-PODIPY, developed from classical conventional BODIPY/azaBODIPY. Besides the advantages of the spectral properties of classical BODIPY/azaBODIPY dyes, the biggest feature is good water solubility. Antimony and its compounds have found use in various fields of basic chemistry and applied chemistry. The synthesis of structure-specific and supraatomic group 15 compounds has attracted increasing attention. In particular, the applicant has made long-term studies in experimental and theoretical chemistry on penta-complex 10-Pn-5 (Pn: P, as, sb, bi). Also, the Sb-BODIPY derivatives, i.e., 10-Sb-5 species, show strong affinity for anions including fluoride and cyanide, the reaction of which causes a fluorescent switching response.
For unstable hexacoordinated antimony complexes, only a few hexacoordinated organic antimony complexes have been reported so far.
Thus, the applicant herein first introduced antimony into azadipyrromethene to build new functional hexacoordinated organoantimony dyes. Based on the early basic accumulation of superatomic chemistry and BODIPY dyes, new strategic designs were introduced to develop a novel azadipyrrin-anti-imjust (VI) (aza-SbDIPY) dye that complexes SbF with azadipyrromethene 5 And the developed aza-SbDIPY is a novel series of dyes with a mother nucleus. As a novel dye, the novel aza-SbDIPY has a higher extinction coefficient, and long wavelength absorption from visible to near infrared region. Aza-SbDIPY can tolerate a small amount of water, can exist stably, and can explore its efficiency in generating singlet oxygen under low humidity conditions.
Disclosure of Invention
The invention aims to provide an antimony complex dye (SbDIPY) and a preparation method thereof, wherein the central atom of the antimony complex dye is a six-coordinate dye complexed by Sb, and the dye has good extinction coefficient and long-wavelength absorption from visible light to near infrared region. Aza-SbDIPY can tolerate a small amount of water, can exist stably, and allows its efficiency in generating singlet oxygen under low humidity conditions.
The invention aims at realizing the following technical scheme:
an antimony complex dye (SbDIPY) has a structural formula shown in formula I/II/III:
。
the central atom of the dye is hexacoordinated 15-group element antimony (Sb).
A method for preparing an antimony complex dye (SbDIPY), comprising the steps of: dissolving bidentate ligand azadipyrromethene VII/VIII/IX in dichloromethane solvent at room temperature in air, adding SbF 5 And the mixture was stirred for 0.5. 0.5 h, and filtered to obtain a mixture; n-hexane was slowly added and the product was recrystallized and purified by methylene chloride/n-hexane mixed solvent to give quantitative product (97% -98%) as a dark green solid aza-SbDIPY of formula I/II/III:
the antimony complex dye (SbDIPY), which is used as a dye for a photosensitizer, generates singlet oxygen under long wavelength monochromatic light irradiation.
The invention has the advantages and effects that:
aiming at the defects of the existing dye, the invention designs and synthesizes a novel dye, and enriches the types of dye families. Meanwhile, the dye has easy modification of molecules.
The aza-SbDIPY dye has optical property and can be used as a photosensitizer to generate singlet oxygen.
The aza-SbDIPY dye has the advantages of small toxicity and side effects, easily available raw materials, simple structure and easy preparation.
The aza-SbDIPY dye has higher extinction coefficient and wider half-peak width.
The aza-SbDIPY dyes of the invention are sensitive to water.
The aza-SbDIPY dye can exist stably under trace water, and can allow the exploration of the singlet oxygen generation efficiency under the condition of low humidity.
Drawings
FIG. 1 is a structural formula I of the novel aza-SbDIPY dye of the invention;
FIG. 2 is a structural formula II of the novel aza-SbDIPY dye of the invention;
FIG. 3 is a structural formula III of the novel aza-SbDIPY dye of the invention;
FIG. 4 is a novel aza-SbDIPY dye I of the invention 1 H NMR nuclear magnetic resonance spectrum;
FIG. 5 is a novel aza-SbDIPY dye I of the invention 19 F NMR nuclear magnetic resonance spectrum;
FIG. 6 is a novel aza-SbDIPY dye II of the invention 1 H NMR nuclear magnetic resonance spectrum;
FIG. 7 is a novel aza-SbDIPY dye II of the invention 19 F NMR nuclear magnetic resonance spectrum;
FIG. 8 is a novel aza-SbDIPY dye III of the invention 1 H NMR nuclear magnetic resonance spectrum;
FIG. 9 is a novel aza-SbDIPY dye III of the invention 19 F NMR nuclear magnetic resonance spectrum;
FIG. 10 is a high resolution mass spectrum of the novel aza-SbDIPY dye I of the invention;
FIG. 11 is a high resolution mass spectrum of the novel aza-SbDIPY dye II of the invention;
FIG. 12 is a high resolution mass spectrum of the novel aza-SbDIPY dye III of the invention;
FIG. 13 is a novel aza-SbDIPY dye of the invention in CH 2 Cl 2 And the absorption spectrum at 298K. Wherein 1a,1b,1c represent azadipyrromethene VII/VIII/IX, respectively; 2a,2b,2c represent photographs of the aza-SbDIPys dye I/II/III, respectively;
FIG. 14 is a theoretical calculation comparison of novel aza-SbDIPY dye III of the invention with conventional aza-BODIPY dye III-1;
FIG. 15 shows the novel aza-SbDIPY dye II of the invention in the presence of different moisture MeCN-H 2 Absorption spectrum in O (2.5 ml). The inset shows that the novel aza-SbDIPY dye II is at 0,0.005,0.01,0.015,0.02,0.025,0.3,0.035 and 0.04ml H 2 Absorption change in the presence of O;
FIG. 16 is a graph of the change in DPBF with time for oxidation of DPBF with absorption at 416nm using the novel aza-SbDIPY dye II of the present invention, which generates singlet oxygen upon irradiation;
FIG. 17 is a graph showing the degradation characteristics and absorption curves of the novel aza-SbDIPY dye of the invention with 1, 3-diphenyl isobenzofuran in MeCN after illumination.
Detailed Description
The present invention will be described in detail with reference to the embodiments shown in the drawings.
In order to overcome the defects of the existing BODIPY/azaBODIPY dye, the first aspect of the invention provides a novel compound aza-SbDIPY with simple structure, long wavelength, higher extinction coefficient and wider half-peak width. It has the following structural formula I/II/III:
I/II/III
in another aspect of the invention, an open system, i.e., synthesis under air, is employed comprising the steps of:
(1) Adding excessive NaH into a round-bottom flask, and washing with dry n-hexane three times under the protection of nitrogen; dropwise adding dry DMSO and corresponding ketone, stirring at room temperature for half an hour, adding the compound 2-phenylazacyclopropene, reacting at room temperature for 2 h, then quenching with ice water, extracting with dichloromethane, washing, drying, and performing column chromatography to obtain pyrrole IV/V/VI.
IV/V/VI
(2) Under an open system, adding corresponding pyrrole, glacial acetic acid and acetic anhydride into a round-bottom flask, adding sodium nitrite under ice water bath, reacting at room temperature for 0.5. 0.5 h, washing with sodium bicarbonate water, extracting with dichloromethane, and spin-drying. Dichloromethane is used as eluent, alumina is used as stationary phase, the column is passed, and solvent is dried by spin to obtain azamethine dipyrrole VII/VIII/IX blue-green solid.
VII/VIII/IX
(3) At room temperature in air, the precursor VII/VIII/IX is dissolved in CH 2 Cl 2 Adding SbF into the solution 5 And the mixture was stirred for 0.5. 0.5 h, and the resulting mixture was filtered. N-hexane was slowly added and passed through CH 2 Cl 2 Recrystallisation of the n-hexane mixed solvent and purification of the product yielded almost quantitative product (97% -98%). To obtain black-green solid aza-SbDIPY with structural formula I/II/III.
I/II/III
In yet another aspect of the present invention, a synthetic aza-SbDIPY reaction mechanism is presented on the basis of the above experiments. The electron pair from the N atom in azadipyrromethene VII first attacks the central atom Sb, then SbF 5 Cleavage of the upright bond of F - . The hydrogen of the pyrrole in the intermediate is then reacted with nucleophile F - Attack, the target compound I is obtained. This is known from the literature as the first synthesis of aza-SbDIPY.
A mechanism diagram of aza-SbDIPY was synthesized.
The aza-SbDIPY was found to have optical properties. Compared to the maximum absorbance of precursor VII (598 nm), the maximum absorbance of aza-SbDIPY dye I is 634 nm, red shifted by 36 nm. The color of the solution varies significantly from blue to green. Similarly, the aza-SbDIPYs dyes II (692 nm) and III (724 nm) have a significant red shift compared to the corresponding precursors VIII (616 nm) and IX (634 nm), respectively. Compared to typical aza-BODIPY dyes II-1 (688 nm) and III-1 (706 nm), the aza-SbDIPys dyes II and III absorb at 692 nm and 724 nm and are unexpectedly red shifted by 4 nm and 18 nm.
II-1/III-1
Aza-SbDIPY is sensitive to water. Dye II (1.2X10 were observed -5 M) has a pronounced response to water (0-0.4. 0.4 ml). As the water content increases, the absorption band at 700 nm gradually decreases, the blue shift band at 620 nm increases, and when 0.4 ml H is added 2 At O, the aza-SbDIPY dye II is completely converted to its precursor VIII. In any event, the aza-SbDIPY is stable in the presence of a small amount of water that can be tolerated, thus allowing their smooth synthesis in air.
The invention adopts a one-pot method to prepare the dye, and azadipyrromethene is complexed with SbF 5 And the developed azadipyrrin-anti-copy (VI) (aza-SbDIPY) is a novel series of dyes as a parent nucleus.
Specific embodiments are described below.
(1) Adding excessive NaH into a round-bottom flask, and washing with dry n-hexane three times under the protection of nitrogen; dropwise adding dry DMSO and corresponding ketone, stirring at room temperature for half an hour, adding the compound 2-phenylazacyclopropene, reacting at room temperature for 2 h, then quenching with ice water, extracting with dichloromethane, washing, drying, and performing column chromatography to obtain pyrrole IV/V/VI.
IV/V/VI
(2) Under an open system, adding corresponding pyrrole, glacial acetic acid and acetic anhydride into a round-bottom flask, adding sodium nitrite under ice water bath, reacting at room temperature for 0.5. 0.5 h, washing with sodium bicarbonate water, extracting with dichloromethane, and spin-drying. Dichloromethane is used as eluent, alumina is used as stationary phase, the column is passed, and solvent is dried by spin to obtain azadipyrromethene VII/VIII/IX blue-green solid.
VII/VIII/IX
(3) At room temperature in air, the precursor VII/VIII/IX is dissolved in CH 2 Cl 2 Adding SbF into the solution 5 And the mixture was stirred for 0.5. 0.5 h, and the resulting mixture was filtered. N-hexane was slowly added and passed through a reaction vessel from CH 2 Cl 2 Recrystallisation from n-hexane and purification of the product gives almost quantitative product (97% -98%) as a dark green solid aza-SbDIPY of formula I/II/III.
I/II/III
The nuclear magnetic resonance spectrum of the compound of the invention comprises 1 H、 19 F NMR nuclear magnetic resonance spectroscopy, mass spectrometry, and the like.
Example 1
Preparation of aza-SbDIPY dye III
(1) Synthesis of pyrrole VI containing a naphthalene ring.
(2) 150 mg NaH was added to a round bottom flask and washed three times with dried n-hexane (10 ml) under nitrogen; dry DMSO (5 ml), 6-methoxy-2-acetylnaphthalene (200 mg, 1 mmol) was added dropwise, stirred at room temperature for half an hour, compound 2-phenylazacyclopropene (175 mg, 1.5 mmol) was added, reacted at room temperature for 2 h, quenched with ice water. Regulating to neutrality with dilute hydrochloric acid, extracting with dichloromethane, washing, drying with anhydrous magnesium sulfate, and elutingn-hexane : CH 2 Cl 2 Column chromatography was performed to synthesize the azure pyrrole VI (89 mg, 30%) with the parallel ring structure. 1 H NMR (500 MHz, CDCl 3 ): δ(ppm)8.56 (br s, 1H), 7.84 (d, 4 J = 1.5 Hz, 1H), 7.77 (d, 3 J = 8.5 Hz, 1H), 7.74 (d, 3 J = 9.0 Hz, 1H), 7.67 (dd, 3 J = 9.0 Hz, 4 J = 2.0 Hz, 1H), 7.60 (dd, 3 J = 8.5 Hz, 4 J = 1.5 Hz, 2H), 7.37 (t, 3 J = 8.0 Hz, 2H), 7.18-7.22 (m, 2H), 7.16 (dd, 3 J = 9.0 Hz, 4 J = 2.0 Hz, 1H), 7.13 (d, 4 J = 2.0 Hz, 1H), 6.90-6.91 (m, 1H), 3.93 (s, 3H)。MS (ESI(+)): m/z = 300.1 [M+H] + , found 300.1。
(3) Pyrrole VI (60 mg, 0.2 mmol), glacial acetic acid (1 ml), acetic anhydride (0.5 ml) and sodium nitrite (6.9 mg,0.1 mmol) were added under open system, and the reaction was carried out at 80 degrees, 0.5 h, sodium bicarbonate water washing, dichloromethane extraction, spin drying. Dichloromethane is used as eluent, alumina is used as stationary phase, the column is passed, and solvent is dried by spin to obtain azamethine dipyrrole IX deep blue solid.
(4) Synthesis of Aza-SbDIPY dye.
At room temperature in air, sbF 5 (8.4. Mu.L, 0.11 mmol) was added to precursor IX (68.2 mg,0.11 mmol) in CH 2 Cl 2 (10 mL) and the mixture was stirred at room temperature for 0.5. 0.5 h. Then, the mixture was filtered. N-hexane (5 mL) was slowly added and passed through CH 2 Cl 2 The product was recrystallized and purified from n-hexane mixed solvent to give III (86.3, mg, 97%) as a dark green solid. 1 H NMR (400 MHz, CD 2 Cl 2 ): δ (ppm) 7.86 (s, 2H), 7.78 (t, 3 J= 8.0 Hz, 4H), 7.69 (d, 3 J = 8.0 Hz, 2H), 7,59 (d, 3 J = 8.0 Hz, 4H), 7.36 (t, 3 J = 8.0 Hz, 4H), 7.14-7.23(m, 6H), 6.91 (s, 2H), 3.92 (s, 6H). 19 F NMR (376 MHz, CD 2 Cl 2 ): δ (ppm) -135.8 (br s, 4F). FTMS-MALDI (m/z): [M+H] + calcd for C 42 H 31 F 4 N 3 O 2 Sb: 806.1391, found 806.1392.
And (3) detecting singlet oxygen.
By adopting an ultraviolet spectrophotometry tracking method, 1, 3-diphenyl isobenzofuran (DPBF) is used as a singlet oxygen scavenger, and the efficiency of generating singlet oxygen by the photosensitizer is evaluated by detecting the decrease of the absorbance of the DPBF. Using monochromatic light (680 nm,0.5 mW/cm) 2 ). DPBF (initial)The concentration of the dye was 5.5X10-5 mol/L) and the aza-BODIPY 2b (1.1X10-5 mol/L) were subjected to light irradiation in MeCN to obtain the degradation characteristics and absorption profile of DPBF (aza-BODIPY dye IIlambda in MeCN) abs = 696 nm）。
The photosensitizer undergoes a DPBF degradation mechanism under illumination.
The effect of generating singlet oxygen of aza-SbDIPY without Br/I was studied for aza-BODIPY photosensitizers modified with specific gravity atoms (Br or I). Using the 1, 3-Diphenylisobenzofuran (DPBF) process, it was found that aza-SbDIPY II with an antimony atom as the central atom was able to produce singlet oxygen, although the ability of aza-SbDIPY to produce singlet oxygen was lower than aza-BODIPY. Experimental results show that the aza-SbDIPY II is stable under illumination and does not have a bleaching phenomenon.
The foregoing is a further detailed description of the invention in connection with specific preferred embodiments, and it is not intended that the invention be limited to the specific embodiments described. For those skilled in the art, on the premise that the core concept of the invention is to complex the azadipyrromethene ligand with Sb, several simple deductions and substitutions can be made, such as other modified azadipyrromethene and complexes of common dipyrromethene bidentate ligands with Sb, which should be regarded as falling within the scope of the invention. As a person skilled in the art, in view of the functionalization of the dye according to the invention for photosensitizers, several other functional enhancements such as cell imaging, molecular probes, fluorescent materials, photosensitizing dyes, photothermal dyes, etc. may be made, and other applications for the compounds according to the invention may be obtained, which should be considered as falling within the scope of the invention.

Claims (3)

1. An antimony complex dye is characterized in that the structural formula is shown as the formula I/II/III:
。
2. the antimony complex dye according to claim 1, wherein the preparation method of the antimony complex dye comprises the following steps: dissolving bidentate ligand azadipyrromethene VII/VIII/IX in dichloromethane solvent at room temperature in air, adding SbF 5 And the mixture was stirred for 0.5. 0.5 h, and filtered to obtain a mixture; n-hexane was slowly added and the product was recrystallized and purified by methylene chloride/n-hexane mixed solvent to give the following quantitative: 97% -98% of the product, which is a black green solid aza-SbDIPY, having the structural formula I/II/III:
。
3. the antimony complex dye according to claim 1, wherein the dye is used as a dye for a photosensitizer, generating singlet oxygen under long wavelength monochromatic light irradiation.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006195399A (en) * 2004-03-09 2006-07-27 Mitsubishi Chemicals Corp Near-infrared absorption filter
CN104356680A (en) * 2014-11-18 2015-02-18 沈阳化工大学 Water-soluble PnO2-PODIPY/PnO2-azaPODIPY fluorescent dye and preparation method thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006195399A (en) * 2004-03-09 2006-07-27 Mitsubishi Chemicals Corp Near-infrared absorption filter
CN104356680A (en) * 2014-11-18 2015-02-18 沈阳化工大学 Water-soluble PnO2-PODIPY/PnO2-azaPODIPY fluorescent dye and preparation method thereof

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