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D-pai-A-pai-D type BODIPY (boron-dipyrromethene) derivatives based on acetenyl bridging and preparation method of D-pai-A-pai-D type BODIPY derivatives

An ethynyl and derivative technology, applied in the field of organic small molecule solar cell materials, can solve the problems of lack of sufficient molecular design and synthesis route optimization, low photovoltaic efficiency, single structure, etc., and achieves easy control of synthesis reaction conditions and wide ultraviolet absorption. Scope, effect of novel molecular structures

Active Publication Date: 2017-06-30
邳州市润宏实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, so far, there are not many reports on the application of BODIPY derivatives in organic solar cells, lack of sufficient design of molecules and necessary optimization of synthetic routes, and there are problems such as single structure and low photovoltaic efficiency.

Method used

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  • D-pai-A-pai-D type BODIPY (boron-dipyrromethene) derivatives based on acetenyl bridging and preparation method of D-pai-A-pai-D type BODIPY derivatives
  • D-pai-A-pai-D type BODIPY (boron-dipyrromethene) derivatives based on acetenyl bridging and preparation method of D-pai-A-pai-D type BODIPY derivatives
  • D-pai-A-pai-D type BODIPY (boron-dipyrromethene) derivatives based on acetenyl bridging and preparation method of D-pai-A-pai-D type BODIPY derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Synthesis of target molecule BDP1

[0101] Add intermediate 3 (65mg, 0.1mmol), intermediate 4 (55mg, 0.25mmol), CuI (2mg, 0.01mmol), PdCl 2 (PPh 3 ) 2 (7mg, 0.01mmol), toluene (10mL) and 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) = 10:1] to obtain dark green solid BDP1 (59 mg), yield 71%. 1 H NMR (400MHz, CDCl 3 )δ:8.10(s,2H),7.70(dd,J=6.5,2.6Hz,4H),7.61–7.54(m,4H),7.48–7.42(m,4H),7.34(dd,J=6.0, 2.7Hz, 4H), 7.13(s, 2H), 7.06(d, J=8.7Hz, 2H), 4.07(t, J=6.5Hz, 2H), 1.89–1.83(m, 2H), 1.49(s, 12H), 1.31(d, J=6.6Hz, 10H), 0.88(d, J=3.6Hz, 3H). 13 C NMR (101MHz, CDCl 3 )δ:162.33,1...

Embodiment 2

[0103] Synthesis of target molecule BDP2

[0104] The synthesis method of BDP2 was similar to the synthesis method of BDP1. Intermediate 3 (65 mg, 0.1 mmol) and intermediate 5 (76 mg, 0.25 mmol) were used as substrates to obtain dark green solid BDP2 (68 mg) with a yield of 68%. 1 H NMR (400MHz, CDCl 3 )δ:8.13(s,2H),8.07(d,J=7.7Hz,2H),8.04(d,J=8.0Hz,2H),7.60(d,J=8.6Hz,2H),7.54(s, 2H), 7.46(d, J=7.2Hz, 2H), 7.40(d, J=8.2Hz, 2H), 7.35(d, J=8.0Hz, 2H), 7.22(d, J=7.3Hz, 2H) ,7.16(s,2H),7.07(d,J=8.7Hz,2H),4.28(t,J=7.2Hz,4H),4.08(t,J=6.5Hz,2H),1.92–1.83(m, 6H),1.36–1.24(m,30H),0.89–0.85(m,9H). 13 C NMR (101MHz, CDCl 3 )δ:162.31,146.11,141.18,140.00,134.83,132.69,132.20,126.25,125.68,123.10,122.48,122.33,120.61,120.34,119.49,119.18,115.07,114.84,113.20,111.81,108.87,94.01,81.57,68.50 ,43.22,31.85,31.82,29.73,29.40,29.27,29.20,29.15,28.98,27.33,26.06,22.70,22.63,14.14,14.09. 67 h 73 BF 2 N 4 O[M] + :998.585; found 998.294.

Embodiment 3

[0106] Synthesis of target molecule BDP3

[0107]The synthesis method of BDP3 is similar to the synthesis method of BDP1, using intermediate 3 (65mg, 0.1mmol) and intermediate 6 (124mg, 0.25mmol) as substrates, the dark green solid BDP2 (95mg) was purified with a yield of 69%. 1 H NMR (400MHz, CDCl 3 )δ: 8.03(s, 2H), 7.56(d, J=8.5Hz, 2H), 7.26(dd, J=8.5, 5.5Hz, 12H), 7.04(d, J=8.6Hz, 4H), 7.01( s,4H),6.99(s,4H),6.94(s,2H),6.92(s,2H),4.06(t,J=6.5Hz,2H),1.88–1.81(m,2H),1.71(s ,8H),1.36(m,34H),0.75(m,39H). 13 C NMR (101MHz, CDCl 3 )δ:162.32,148.41,146.00,145.48,144.20,132.61,132.27,127.12,125.74,125.71,124.39,121.23,114.78,114.51,93.03,81.01,68.45,57.17,38.26,32.44,31.84,31.75,31.44,29.72 , 29.34, 29.26, 29.14, 26.04, 22.69, 14.13. MALDI-TOF-MS, m / z: calcd for C 95 h 117 BF 2 N 4 O[M] + :1378.929; found 1378.320.

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Abstract

The invention discloses D-pai-A-pai-D type BODIPY (boron-dipyrromethene) derivatives based on acetenyl bridging and a preparation method of the D-pai-A-pai-D type BODIPY derivatives. The derivatives are novel and are obtained by linking acetenyl to fluorine, carbazole, triphenylamine, benzodithiophene, phenothiazine and other groups and then subjecting the groups with acetenyl to a Sonogashira coupling reaction with prepared BODIPY with bilateral iodine substitutes in 2 and 6 positions. The synthesis method of the D-pai-A-pai-D type BODIPY derivatives based on acetenyl bridging is simple, is higher in yield, has general applicability and can realize efficient synthesis, and the reaction conditions are easy to control; the D-pai-A-pai-D type BODIPY derivatives can be widely applied to the fields such as energy, life, analysis, material science and the like and are particularly suitable for serving as organic micromolecule solar cell materials and the like.

Description

[0001] Technical field: [0002] The invention relates to a D-π-A-π-D type BODIPY derivative based on ethynyl bridging and a preparation method thereof. The derivative can be widely used in the fields of energy, environment, life, analysis, material science and the like , especially suitable as organic small molecule solar cell materials, etc. [0003] Background technique: [0004] Boron fluoride complexed with dipyrromethene (abbreviated as BODIPY) is a new type of fluorescent compound that has been developed in the past 20 to 30 years and has received widespread attention and attention. BODIPY derivatives are a kind of good photosensitive dyes with good stability, modifiability, high molar extinction coefficient (1×105M-1cm-1) and high oxidation potential, and they can be modified in many positions , by selectively accessing groups with corresponding functions to adjust the optical properties, stability and chemical properties of BODIPY dyes such as absorption wavelength, e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC09K11/06C07F5/022C09K2211/1096H10K85/657Y02E10/549
Inventor 赵鸿斌宗乔廖俊旭韩利芬张文涛彭飞鲁浩沈松平
Owner 邳州市润宏实业有限公司
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