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Meso-ethynyl bridged D-Pi-A type BODIPY dye and preparation method thereof

An ethynyl and bridging technology, which is applied in the direction of methynyl/polymethynyl dyes, organic dyes, chemical instruments and methods, etc., can solve problems such as difficult to obtain, and achieve easy control of reaction conditions, universal applicability, and product Purify Simple Effects

Inactive Publication Date: 2017-08-04
DONGGUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Relevant literature reports that after introducing various functional groups into the meso-position of the BODIPY core, due to the influence of steric hindrance, it is difficult to form an effective conjugation with the fluorine-boron core plane, which has little effect on the spectral properties of the dye molecule, and is difficult to Obtain meso-position-substituted BODIPY dyes with excellent performance, so there are relatively few research reports on meso-position-modified BODIPY dyes

Method used

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  • Meso-ethynyl bridged D-Pi-A type BODIPY dye and preparation method thereof
  • Meso-ethynyl bridged D-Pi-A type BODIPY dye and preparation method thereof
  • Meso-ethynyl bridged D-Pi-A type BODIPY dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Synthesis of BDP1:

[0080] Add intermediate 3 (226mg, 1.0mmol), intermediate 4 (262mg, 1.2mmol), anhydrous THF (20mL) and anhydrous Et to a 50mL three-neck flask in sequence 3 N (2mL), the system was evacuated, protected by argon, the reaction bottle was placed in an ice-water bath, and CuI (10mg, 0.05mmol) and Pd(PPh 3 ) 2 Cl 2 (35mg, 0.05mmol), stirred magnetically at 0°C for 30min. Stop the reaction, pour into 50mL distilled water, extract with ethyl acetate (30mL×3), wash the organic phase with saturated brine (30mL×3), anhydrous Na 2 SO 4 Let dry overnight. The filtrate was collected by filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel (200-300 mesh) column chromatography [eluent, V (petroleum ether): V (ethyl acetate) = 16:1] to obtain a red solid BDP1 (290 mg), yield 71%. 1 H NMR (400MHz, CDCl 3 )δ:7.84(s,2H),7.82–7.77(m,2H),7.70(d,J=0.7Hz,1H),7.67(dd,J=7.8,1.4Hz,1H),7.51–7.45(m ,3H),7.44–7.37(m,2H...

Embodiment 2

[0082] Synthesis of BDP2:

[0083] The synthesis method of BDP2 was similar to the synthesis method of BDP1. Intermediate 3 (226mg, 1.0mmol) and intermediate 5 (564mg, 1.2mmol) were used as substrates to obtain dark red solid BDP2 (390mg) with a yield of 59%. 1 H NMR (400MHz, CDCl 3 )δ:7.94(s,1H),7.85(s,2H),7.49(q,J=5.6Hz,2H),7.43(d,J=4.0Hz,2H),6.59(d,J=3.3Hz, 2H), 4.35(t, J=6.6Hz, 2H), 4.28(t, J=6.6Hz, 2H), 1.96–1.86(m, 4H), 1.35(d, J=25.9Hz, 20H), 0.90( dd,J=6.7,4.7Hz,6H). 13 C NMR (101MHz, CDCl 3 )δ:145.67,143.90,143.68,136.16,134.22,131.02,130.62,130.46,130.40,128.98,128.15,126.37,120.44,119.62,118.51,99.68,90.05,74.42,74.18,31.88,30.56,29.45,29.34,26.08 , 22.73, 14.19. MALDI-TOF-MS, m / z: calcd for C 37 h 43 BF 2 N 2 o 2 S 2 [M] + :660.283,found:660.183.

Embodiment 3

[0085] Synthesis of BDP3:

[0086]The synthesis method of BDP3 was similar to the synthesis method of BDP1. Intermediate 3 (226 mg, 1.0 mmol) and intermediate 6 (402 mg, 1.2 mmol) were used as substrates to obtain BDP3 (326 mg) as a purple-black solid with a yield of 62%. 1 H NMR (400MHz, CDCl 3 )δ: 7.81(s, 2H), 7.45(dd, J=8.5, 1.9Hz, 1H), 7.39–7.34(m, 3H), 7.18(dd, J=11.1, 4.5Hz, 1H), 7.12(dd ,J=7.6,1.5Hz,1H),6.97(t,J=7.0Hz,1H),6.87(dd,J=14.6,8.2Hz,2H),6.55(d,J=2.8Hz,2H),3.92 –3.85(m, 2H), 1.81(dd, J=14.9, 7.6Hz, 2H), 1.56–1.18(m, 10H), 0.87(t, J=6.8Hz, 3H). 13 C NMR (101MHz, CDCl 3 )δ:148.06,143.63,142.77,136.21,132.82,131.28,128.51,127.76,127.65,127.57,125.05,123.49,118.04,115.93,115.12,114.05,107.56,107.52,85.76,47.88,31.76,29.23,29.19,26.85 , 26.76, 22.66, 14.15. MALDI-TOF-MS, m / z: calcd for C 31 h 30 BF 2 N 3 S[M] + :525.222,found:525.203.

[0087] The photophysical and thermal stability related data of the target dye BDP1-3 in the above examples are shown in T...

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Abstract

The invention discloses meso-ethynyl bridged D-Pi-A type BODIPY dye and a preparation method thereof. According to the dye, ethynyl is introduced on groups such as fluorene, benzene thiophene and phenthazine at first, and then the groups and a synthesized meso-cl substituted BODIPY unit are subjected to coupled reaction through Sonogashira to obtain the meso-ethynyl bridged D-Pi-A type BODIPY dye I. The synthesis method of the dye is simple, reaction conditions are easily controlled, yield is high, universal applicability is high, the meso-ethynyl bridged D-Pi-A type BODIPY dye can be synthesized efficiently; and the meso-ethynyl bridged D-Pi-A type BODIPY dye can be widely applied to scientific fields of energy, life, analysis, materials and the like, and is particularly suitable for being used as an organic small molecule solar battery donor material.

Description

[0001] Technical field: [0002] The invention relates to a D-π-A type BODIPY dye with meso-position ethynyl bridging and a preparation method thereof. The dye can be widely used in energy, environment, life, analysis, materials and other scientific fields, and is especially suitable as a Donor materials for organic small molecule solar cells. [0003] Background technique: [0004] Boron fluoride-complexed dipyrromethene (BODIPY) compounds are a new type of fluorescent dyes that have emerged in recent decades and have been extensively studied. It has good stability, flexible modifiability, high molar extinction coefficient (1×10 5 m -1 cm -1 ) and higher oxidation potential. In view of the unique photophysical properties, chemical properties and modifiability of BODIPY dyes, its spectral properties can be adjusted by introducing different substituents at different active sites or changing the length of the conjugated chain to enhance its applicability. In recent decades, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09B23/12C09K11/06
CPCC07F5/022C09B23/12C09K11/06C09K2211/1029C09K2211/1037C09K2211/1055
Inventor 赵鸿斌宗乔廖俊旭韩利芬张文涛彭飞林升衡杨芷青
Owner DONGGUAN UNIV OF TECH
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