CN111718365B - Trimeric indenyl conjugated tri-BODIPY near-infrared fluorescent dye and preparation method thereof - Google Patents
Trimeric indenyl conjugated tri-BODIPY near-infrared fluorescent dye and preparation method thereof Download PDFInfo
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- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 27
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title abstract description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 18
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 13
- 230000003197 catalytic effect Effects 0.000 claims abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 5
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 239000013638 trimer Substances 0.000 claims 1
- -1 trimethyloylindene Chemical compound 0.000 claims 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000008033 biological extinction Effects 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000000862 absorption spectrum Methods 0.000 abstract 1
- 239000000090 biomarker Substances 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000003609 aryl vinyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- OVTCUIZCVUGJHS-UHFFFAOYSA-N dipyrrin Chemical compound C=1C=CNC=1C=C1C=CC=N1 OVTCUIZCVUGJHS-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 238000001215 fluorescent labelling Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
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- 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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract
The invention relates to a trimeric indenyl conjugated tri-BODIPY near-infrared fluorescent dye and a preparation method thereof, which is synthesized by performing Knoevenagel condensation reaction on a BODIPY derivative and 2, 7, 12-trimethylacyltruxene under the catalytic action of p-toluenesulfonic acid and piperidine. The preparation method has the advantages of simple reaction steps, mild reaction conditions and good selectivity. The fluorescent dye has excellent photophysical properties such as high molar extinction coefficient, good solubility and light stability, the strongest electron absorption spectrum of the fluorescent dye is red-shifted to be more than 650nm, the maximum fluorescence emission wavelength reaches to be more than 700nm, and the fluorescent dye is a near-infrared organic fluorescent dye with a good application prospect and can be applied to the fields of biological markers, fluorescent probes, photovoltaic materials and the like.
Description
Technical Field
The invention belongs to the technical fields of organic compound synthesis, functional fluorescent dyes and fine chemical engineering, and particularly relates to a trimeric indenyl conjugated tri-BODIPY near-infrared fluorescent dye and a preparation method thereof.
Background
Boron dipyrromethene (BODIPY) dye is popular in the scientific community as near infrared organic fluorescent dye due to its excellent photo-physical properties and easily modified chemical structure. They have higher molar extinction coefficient and fluorescence quantum yield; strong absorption in the visible region; is not easily influenced by the polarity of the solvent; has better photo-thermal stability, and can avoid the influence of detection environment changes such as excitation irradiation, temperature rise and the like on fluorescence analysis. Therefore, the BODIPY compounds have great application value in the fields of photodynamic therapy, ion recognition, pH fluorescent probes, cell imaging and tracing, protein and DNA labeling, novel dye-sensitized solar cells and the like.
The near-infrared organic fluorescent dye has wide application in the fields of fluorescence imaging, fluorescence identification, environmental monitoring, tumor diagnosis and the like, so that the research and development has raised the heat tide of synthesizing near-infrared fluorescent molecules. In recent years, BODIPY dyes have gained widespread scientific interest due to their superior photophysical chemical properties and diverse applications. Compared with the traditional fluorescent dye, such as fluorescein, rhodamine and the like, the BODIPY compound has higher molar absorption coefficient, fluorescence quantum yield and fluorescence life; the fluorescent signal is insensitive to solvent polarity and pH; strong absorption in the visible region; better photo-thermal stability and the like. Moreover, the BODIPY molecule has certain chemical activity and can regulate the structure and the performance. Particularly, methyl groups at 3 and 5 positions of the BODIPY parent nucleus have certain chemical activity and can perform Knoevenagel condensation reaction with aromatic aldehyde, so that different types of aryl vinyl can be introduced to form a larger aromatic ring conjugated system with the BODIPY main body, and the electron absorption and emission wavelengths of the compounds are obviously red-shifted. Therefore, the near-infrared BODIPY derivatives can be prepared by modifying the 3, 5-position of the BODIPY through aryl vinyl.
Most of the existing near-infrared BODIPY dyes have multiple synthesis steps, high difficulty and poor solubility, and limit the further application of the dyes in the fields of biology, environment, medicine and the like. The truxene is a triply symmetrical polycyclic aromatic hydrocarbon, has a large rigid conjugated structure and higher light and heat stability, and is an organic photoelectric material with an easily modified structure. Therefore, the novel near-infrared BODIPY fluorescent dye with novel structure, simple preparation method and excellent performance can be synthesized by forming a conjugated double bond by the BODIPY derivative with methyl at the 5-position and 2, 7 and 12-triacyl truxene through Knoevenagel condensation reaction.
Disclosure of Invention
The purpose of the invention is as follows: aiming at the defects in the prior art, the invention aims to provide a trimeric indenyl conjugated tri-BODIPY near infrared fluorescent dye. The invention also aims to provide a preparation method of the trimeric indenyl conjugated tri-BODIPY near-infrared fluorescent dye.
The technical scheme is as follows: in order to achieve the purpose of the invention, the invention adopts the technical scheme that:
the invention relates to a trimeric indenyl conjugated three-BODIPY near-infrared fluorescent dye and a preparation method thereof, which are characterized in that the structural general formula is as follows:
a preparation method of a trimerization indenyl conjugated tri-BODIPY near infrared fluorescent dye derivative comprises the following steps:
1) under the anhydrous condition, adding a BODIPY derivative, 2, 7, 12-trimethyloyltriphenylindene and newly dried p-toluenesulfonic acid into a round-bottom flask, preparing a Dean-Stark device, dissolving with toluene, adding 1mL of piperidine serving as a catalyst, stirring and heating to reflux for 24-28 hours; wherein the molar ratio of the 2, 7, 12-trimethyloyltriindene to the BODIPY derivative is 1: 3-4.5.
2) Cooling the reactant to room temperature, diluting with dichloromethane, washing with water, drying with anhydrous sodium sulfate, distilling the organic layer under reduced pressure to remove the organic solvent, separating the residue by silica gel column chromatography, and eluting with 100% dichloromethane to obtain a black-green solid product.
The specific chemical reaction formula is as follows:
in the step (1), the molar ratio of the 2, 7, 12-trimethyloyltriindene to the BODIPY derivative is 1: 3-4.5.
In the above step (1), toluene and piperidine were added in an amount of 25mL and 1mL, respectively.
In the step (1), the catalyst is p-toluenesulfonic acid and piperidine.
In the step (2), the eluent for silica gel column chromatography was 100% dichloromethane.
The invention has the advantages of
Compared with the prior art, the near-infrared trimeric indenyl conjugated tri-BODIPY fluorescent dye and the preparation method thereof have the advantages that: (1) the preparation method is simple and easy to implement, can obtain three near-infrared BODIPY derivatives without multi-step reaction, is insensitive to oxygen and humidity, and still has the inherent environmental stability of the BODIPY compounds. (2) The compound has good solubility in organic solvent. (3) The fluorescent dye has narrow absorption peak and fluorescence emission peak in near infrared region, and high molar ratioMolar absorptivity (greater than 3.0X 105cm-1mol-1L) and good light stability, so that the compound has good application prospect in the fields of solar cells, fluorescence labeling, biological imaging and the like.
Drawings
FIG. 1 is a graph of the UV-VIS absorption spectrum of Compound 1;
FIG. 2 is a fluorescence emission spectrum of Compound 1;
FIG. 3 is a graph of the UV-VIS absorption spectrum of Compound 2;
FIG. 4 is a fluorescence emission spectrum of Compound 2.
Detailed Description
The invention is further described below with reference to the specific drawings.
By using1H-NMR and UV-Vis spectrums characterize and confirm the structure of the near-infrared BODIPY fluorescent dye. The detection instrument is as follows: BrukeraRx400 NMR Spectrometer (TMS as internal standard, deuterated chloroform as solvent), Shimadzu UV-3100 UV-visible spectrophotometer (scan range 300-900 nm, light path slit 2nm), fluorescence spectroscopy was tested with American Amico Bowman Series 2 Luminescence Spectrometer.
Example 1
A round-bottomed flask equipped with a Dean-Stark apparatus was charged with 1, 5, 7-tetramethyl-3- (4-N-dimethyl) -vinylbenzene-8- (2, 4, 6-trimethylbenzene) -BODIPY (237mg, 0.477mmol), 2, 7, 12-trimethyloylindene (94mg, 0.159mmol) and freshly dried p-toluenesulfonic acid (79mg) in 25mL of toluene and 1mL of piperidine, the mixture was heated under reflux for 24 hours, cooled to room temperature, diluted with dichloromethane, washed with water, the organic layer was dried over anhydrous sodium sulfate, the organic solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography, and the eluent was (100% CH-CH)2Cl2) Compound 1(32mg, 10%) was obtained as a dark green solid.1H NMR： (400MHz，CDCl3)δ8.46(d，3H)，7.90(d，3H)，7.79(d，3H)，7.67(s，4H)，7.64-7.53(m，8H)，7.39 (d，3H)，7.28(d，3H)，6.99(s，6H)，6.69(t，12H)，3.11(m，6H)，3.04-2.90(m，18H)，2.38(s，9H)， 2.32(dd，6H)，2.17(s，18H)，1.49(d，18H)，0.32(t，18H)。
UV-vis: 338nm, 418nm, 687nm (FIG. 1); emission wavelet: 664nm, 727nm (FIG. 2).
Example 2
A round-bottomed flask equipped with a Dean-Stark apparatus was charged with 1, 5, 7-tetramethyl-3- (4-N, N-diphenylaminostyryl) -8- (2, 4, 6-trimethylbenzene) -BODIPY (415mg, 0.63mmol), 2, 7, 12-trimethyloylindene (128mg, 0.21mmol) and freshly dried p-toluenesulfonic acid (100mg) dissolved in 25mL of toluene and 1mL of piperidine, the mixture was heated under reflux for 28 hours, cooled to room temperature, diluted with dichloromethane, washed with water, the organic layer dried over anhydrous sodium sulfate, the organic solvent evaporated under reduced pressure, the residue purified by silica gel column chromatography, and the eluent was (100% CH)2Cl2) Compound 2 was obtained as a dark green solid (45mg, 9%).1H NMR： (600MHz，CDCl3)δ8.43(d，J＝8.4Hz，3H)，7.86(d，J＝16.2Hz，3H)，7.80(d，J＝7.8Hz，3H)， 7.72(d，J＝16.2Hz，3H)，7.62(s，3H)，7.56(d，J＝8.4Hz，1H)，7.54(d，J＝8.4Hz，6H)，7.43(d，J ＝16.2Hz，3H)，7.39-7.37(m，2H)，7.30(d，J＝7.8Hz，9H)，7.26(d，J＝16.2Hz，3H)，7.14(d，J＝ 7.6Hz，12H)，7.12-7.08(m，12H)，7.01(s，6H)，6.73(s，3H)，6.67(s，3H)，3.08(m，6H)，2.39(s，9H)，2.31-2.25(m，6H)，2.19(s，18H)，1.31(s，18H)，0.29(t，J＝7.2Hz，18H)。
UV-vis(CH2Cl2): 348nm, 404nm, 680nm (FIG. 3); emission wavelet: 716nm (FIG. 4).
Claims (4)
1. A trimeric indenyl conjugated three-BODIPY near infrared fluorescent dye is characterized in that the structural general formula is as follows:
2. the method for preparing the trimeric indenyl conjugated tri-BODIPY near infrared fluorescent dye as claimed in claim 1, which is characterized in that: the method comprises the following steps of taking 2, 7, 12 trimethyloylindene with a structural formula shown in a formula (I) and a BODIPY derivative with a structural formula shown in a formula (II) as raw materials, and generating a target product under the catalytic action of p-toluenesulfonic acid and piperidine, wherein the method comprises the following steps:
1) under the anhydrous condition, adding a BODIPY derivative with a structural formula shown in a formula (II), 2, 7, 12-trimethyloyltriindene with a structural formula shown in a formula (I) and newly dried p-toluenesulfonic acid into a round-bottom flask, preparing a Dean-Stark device, adding 25mL of toluene for dissolving, adding 1mL of piperidine serving as a catalyst, stirring and heating to reflux for 24-28 hours; wherein the molar ratio of the trialdehyde trimer indene to the BODIPY derivative is 1: 3-4.5,
2) cooling the reaction product to room temperature, diluting with dichloromethane, washing with water, separating, drying an organic layer with anhydrous sodium sulfate, distilling under reduced pressure to remove an organic solvent, and separating and purifying the residue by silica gel column chromatography, wherein an eluent is 100% dichloromethane, so as to obtain a black-green solid product.
3. The method for preparing the trimeric indenyl conjugated three-BODIPY near-infrared fluorescent dye according to claim 2, wherein in the step 1), the molar ratio of the 2, 7, 12-triindene to the BODIPY derivative is 1: 3-4.5.
4. The method for preparing the trimeric indenyl conjugated tri-BODIPY near infrared fluorescent dye according to claim 2, wherein the volume ratio of the toluene to the piperidine in the step 1) is 25: 1.
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| CN105462576A (en) * | 2015-09-01 | 2016-04-06 | 南京林业大学 | Near infrared BODIPY fluorescence dye and preparation method thereof |
| CN106928262A (en) * | 2017-03-16 | 2017-07-07 | 南京林业大学 | A kind of double BODIPY fluorochromes of near-infrared trimeric indenyl conjugation and preparation method thereof |
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| Title |
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| Star-shaped multichromophoric arrays from bodipy dyes grafted on truxene core;Diring, Stephane et al;《Journal of the American Chemical Society》;20091231;第131卷;第6108-6110页 * |
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