A kind of a-π-d-π-a type bodipy derivative based on ethynyl bridging and preparation method thereof

A technology of ethynyl derivatives, which is applied in the field of boron fluoride complexed dipyrromethene derivatives, can solve the problems of limited species, complex synthesis, lack of adequate molecular design and synthetic route optimization, etc., and achieve low synthesis cost, π-π The accumulation phenomenon is obvious and the effect is easy to control

Active Publication Date: 2018-08-17
DONGGUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the synthesis of BODIPY dyes reported in the existing literature is complex, with limited types, lack of adequate molecular design and necessary optimization of synthetic routes

Method used

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  • A kind of a-π-d-π-a type bodipy derivative based on ethynyl bridging and preparation method thereof
  • A kind of a-π-d-π-a type bodipy derivative based on ethynyl bridging and preparation method thereof
  • A kind of a-π-d-π-a type bodipy derivative based on ethynyl bridging and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Synthesis of target molecule BDP1:

[0091] Add intermediate 3 (52mg, 0.1mmol), intermediate 4 (110mg, 0.25mmol), CuI (2.0mg, 0.01mmol), PdCl 2 (PPh 3 ) 2 (7mg, 0.01mmol), toluene (10mL), triethylamine (10mL), vacuumize, pass through argon protection, and react with magnetic stirring at room temperature for 12h. Stop the reaction, extract with ethyl acetate, wash with saturated brine, and dry over anhydrous magnesium sulfate. Filtered, and the filtrate was rotovapped to remove the solvent. The crude product was purified by silica gel (200-300 mesh) column chromatography [eluent, V (petroleum ether): V (ethyl acetate) = 5:1] to obtain purple-black solid compound BDP1 (88 mg), yield 72% . 1 H NMR (400MHz, CDCl 3 )δ: 8.06(s,2H),7.98(s,2H),7.64(d,J=7.6Hz,2H),7.57(s,2H),7.55(s,2H),7.48–7.43(m,4H ),7.10(s,2H),7.05(d,J=8.6Hz,6H),6.62–6.58(m,2H),4.06(t,J=6.5Hz,4H),1.97–1.93(m,4H) ,1.89–1.82(m,4H),1.37–1.03(m,40H),0.90(t,J=6.8Hz,6H),0.82(d,J=6.8Hz,6H),0.59(s,4H). 13 C N...

Embodiment 2

[0093] Synthesis of target molecule BDP2

[0094] The synthesis method of BDP2 is similar to the synthesis method of BDP1. Intermediate 3 (52 mg, 0.1 mmol) and intermediate 5 (82 mg, 0.25 mmol) were used as substrates to purify the purple-black solid compound BDP2 (76 mg) with a yield of 68%. . 1 H NMR (400MHz, CDCl 3 )δ:8.08(s,2H),8.02–7.97(m,4H),7.58(d,J=1.9Hz,2H),7.57–7.55(m,2H),7.52(s,2H),7.34(dd ,J=8.1,1.2Hz,2H),7.12(s,2H),7.08–7.04(m,6H),6.60(dd,J=4.3,1.8Hz,2H),4.26(t,J=7.3Hz, 2H), 4.07(t, J=6.5Hz, 4H), 1.86(dd, J=14.2, 7.2Hz, 6H), 1.41–1.24(m, 30H), 0.92–0.85(m, 9H). 13 C NMR (101MHz, CDCl 3 )δ: 162.08, 147.53, 144.88, 144.72, 140.72, 135.48, 134.19, 132.59, 132.34, 131.59(s), 125.83(s), 122.72, 122.58 120.52(s), 120.30(s), 119.15 (s), 114.20(s), 111.85(s), 93.22(s), 82.29(s), 68.45(s), 43.30(s), 31.84(s), 29.39, 29.36, 29.27, 29.21, 29.16, 28.97 , 27.31(s), 26.06(s), 22.69, 22.63, 14.14, 14.10. MALDI-TOF-MS, m / z: calcd for C 70 h 75 B 2 f 4 N 5 o 2 [M] + :...

Embodiment 3

[0096] Synthesis of target molecule BDP3

[0097] The synthesis method of BDP3 is similar to the synthesis method of BDP1. Intermediate 3 (52mg, 0.1mmol) and intermediate 6 (124mg, 0.25mmol) were used as substrates to obtain purplish-black solid compound BDP3 (74mg) with a yield of 58%. . 1 H NMR (400MHz, CDCl 3 )δ:8.04(s,2H),8.00(s,2H),7.56(d,J=7.1Hz,6H),7.07(dd,J=10.8,7.9Hz,8H),6.61(d,J=2.5 Hz, 2H), 4.24(t, J=6.5Hz, 4H), 4.07(t, J=6.5Hz, 4H), 1.85(dd, J=13.3, 6.6Hz, 8H), 1.33(d, J=18.3 Hz,40H),0.92–0.88(m,12H). 13 C NMR (101MHz, CDCl 3 )δ:162.19,147.87,145.62,145.36,144.36,143.83,135.68,134.09,132.83,132.61,131.94,131.54,130.34,125.70,125.11,122.89,119.38,114.77,88.67,85.46,74.17,68.47,53.43,31.85 ,31.83,30.52,29.71,29.41,29.35,29.26,29.15,26.04,26.03,22.68,14.13.MALDI-TOF-MS,m / z: calcd for C 76 h 88 B 2 f 4 N 4 o 4 S 2 [M]+ :1282.637; found1282.170.

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Abstract

The invention discloses an ethynyl bridging based A-phi-D-phi-A type BODIPY derivative and a preparation method thereof. The A-phi-D-phi-A type BODIPY derivative is prepared by the following steps: grafting ethynyl to groups such as fluorene, carbazole, dibenzothiophene, phenothiazine, and the like, and then carrying out Sonogashira coupling reactions between the groups and BODIPY which is substituted with iodine at 2 position. The structure of the derivative is represented by the formula I. The synthesis method of the derivative is simple. The reaction conditions are easy to control. The yield is high. The application range of the derivative is wide. The derivative can be synthesized high efficiently and widely applied to the field of micro-molecular solar cell material.

Description

Technical field: [0001] The invention relates to the field of boron fluoride complexed dipyrromethene derivatives, in particular to an A-π-D-π-A type boron fluoride complexed dipyrromethene derivative based on ethynyl bridges. Background technique: [0002] In recent decades, BODIPY derivatives have achieved rapid development and accumulated a solid research foundation. Researchers have adjusted the BODIPY dye by introducing different substituents at different active sites or changing the length of the conjugated chain. Optical properties such as absorption wavelength, stability, and physical properties such as solubility. Due to the good photochemical stability, high fluorescence quantum efficiency, high molar extinction coefficient and high oxidation potential of BODIPY derivatives, they are widely used in chemical sensors, biomarkers, dye-sensitized solar cells and small molecule solar cells. Batteries and other fields. [0003] However, the synthesis of BODIPY dyes rep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06
CPCC07F5/022C09K11/06C09K2211/1096
Inventor 赵鸿斌宗乔廖俊旭徐勇军刘啸天刘传生刘春辉巫志明
Owner DONGGUAN UNIV OF TECH
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