Triphenylamine-BODIPY derivative organic dye and preparation method thereof

A technology for dipyrromethene and organic dyes, applied in the direction of organic dyes, methine/polymethine dyes, chemical instruments and methods, etc., can solve the problems of pyrrole ring self-polymerization, catalytic decomposition, and low synthesis yield, and achieve reaction The conditions are easy to control, the overall yield is high, and the reaction conditions are more effective.

Inactive Publication Date: 2015-04-29
DONGGUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] According to literature reports, in recent years, people have paid more attention to the influence of substitution at different sites on the BODIPY matrix and the molecular space structure of derivatives on its photoelectric properties, but there is still a long way to go for practical application.
The first thing to be solved is the problem of low synthesis yield of BODIPY dyes. This is due to the problems of self-polymerization and acid-catalyzed decomposition of the pyrrole ring. When some functional groups are introduced, the control of reaction conditions and the simplification of the post-treatment process appear. very critical

Method used

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  • Triphenylamine-BODIPY derivative organic dye and preparation method thereof
  • Triphenylamine-BODIPY derivative organic dye and preparation method thereof
  • Triphenylamine-BODIPY derivative organic dye and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Synthesis of Dye III

[0046] (1) Add 4-bromotriphenylamine (650mg, 2mmol) and 5ml dimethylformamide (DMF) into a 100ml three-necked flask, stir it with a magnetic force, put it in an ice-water bath to 0°C, and slowly add POCl dropwise into the three-necked flask 3 (9ml, 20mmol), and a large amount of solids were formed, after the dropwise addition, the temperature was slowly raised to 60°C, and the temperature was controlled to continue the reaction for 2h, then the reaction was stopped, cooled to room temperature, poured into water, CH 2 Cl 2 Extract, wash with saturated NaCl solution 20ml×3 and distilled water 20ml×3 in sequence, collect the organic phase, dry over anhydrous magnesium sulfate, spin off the solvent under reduced pressure, and the crude product is subjected to column chromatography with petroleum ether as the eluent to obtain the intermediate 620mg of 2(4-bromo-4',4"-diformyltriphenylamine) light yellow crystals, yield 81%. 1 HNMR (400MHz, CDCl 3 TM...

Embodiment 2

[0050] Synthesis of Dye II

[0051] The synthetic method of dye II is similar to that of dye III, except that in the step (1) reaction of synthetic dye III, POCl 3 The molar ratio with DMF is 1:1, and other reaction conditions are the same, and the intermediate 1 is 4-bromo-4'-formyltriphenylamine. The yield of dye II was 81%, and the melting point was 208-210°C. 1 HNMR (400MHz, CDCl 3 TMS,ppm):δ:7.91(s,2H),6.93-7.47(m,15H),6.56(s,2H); 13 CNMR (100MHz, CDCl 3 , TMS, ppm): δ: 147.87, 147.53, 143.61, 133.22, 132.76, 132.67, 132.61, 130.34, 129.83, 127.47, 126.44, 125.58, 124.90, 123.70, 121.08, 115.25. 494.159(obs.)[M-F]+,calcd.avg.mass:513.081.

Embodiment 3

[0053] Synthesis of Dye IV

[0054] Add dye II (200mg, 0.38mmol), 2-octyl-5-(tributyltin)thiophene (200mg, 0.40mmol), 20ml DMF, 120mg of tetrakis(triphenylphosphine)palladium, and extract Vacuum, N 2 Gas protection, temperature control at 90 ° C for 48 hours. Stop the reaction, cool, pour into water, CH 2 Cl 2 Extraction, organic phase anhydrous Na 2 SO 4 Dry, filter, and evaporate the solvent under reduced pressure. The crude product was separated and purified by silica gel column chromatography, the eluent was petroleum ether: ethyl acetate = 15:1, and dye IV was obtained as a purple-black solid viscous substance, 182mg, yield 76%, melting point 93-95°C. 1 HNMR (400MHz, CDCl 3 ,TMS,ppm):δ:6.73-7.67(m,19H),6.39(s,2H),2.79-2.83(t,J=6.5Hz,2H),1.25-1.68(m,12H),0.88(t , J=7.2Hz, 3H). MALDI-TOF-MS: m / z=582.460 (obs.) [M-47]+, calcd.avg.mass: 629.282.

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Abstract

The invention discloses a triphenylamine-BODIPY derivative organic dye and a preparation method thereof. The triphenylamine-BODIPY derivative organic dye is prepared by that a triphenylamine-aldehyde compound is in reaction with pyrrole under the catalytic action of a catalyst, so as to synthetize dipyrromethane, and then a triphenylamine-BODIPY derivative is obtained through further oxidation and fluorine boronizing, and the general formula is shown in a structural formula I. The stokes displacement value of the triphenylamine-BODIPY derivative can reach 180 to 238 nm, and the fluorescence emission peak thereof locates in the near infrared region of 700 to 800 nm. The synthetic method of the compound is simple, the reaction is easy to control, the yield is high, common applicability is achieved, so that the BODIPY dye can be composited efficiently, and can be widely applied to the field of bioscience, analytic chemistry, environmental energy science and the like, and is particularly used as a near-infrared fluorescent dye and an organic solar cell material (refer to the description).

Description

Technical field: [0001] The invention relates to a triphenylamine-substituted boron fluoride complexed dipyrromethene (BODIPY) derivative fluorescent dye and a preparation method thereof. The derivative can be widely used in the fields of life science, analytical chemistry, environmental energy science, etc., especially It can be used as near-infrared fluorescent dye and organic solar cell material. Background technique: [0002] Boron fluoride complexed dipyrromethene (BODIPY) has high photostability and strong spectral absorption, and is not easily affected by solvent polarity and acidity and alkalinity. It is a new class of fluorescent dyes that has received extensive attention. Different substituents and substitutions at different positions will directly affect the photoelectric performance of this type of dye. The introduction of reactive groups such as hydroxyl, sulfonic acid, and carboxyl groups into the BODIPY matrix structure will change the reactivity of the BODIPY...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/04C09B23/10C07F5/02C09K11/06
Inventor 赵鸿斌韩利芬王帮应廖俊旭张文涛周伟男彭敏萧晓君
Owner DONGGUAN UNIV OF TECH
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