Meso-triphenylamine-substituted 3,5-aryl-modified boron dipyrromethene fluorophore derivatives and preparation method thereof

A technology of dipyrromethene and triphenylamine, which is applied in the field of organic solar cell materials, can solve the problems of low synthesis yield and achieve the effects of high product synthesis yield, low production cost, and easier control of reaction conditions

Active Publication Date: 2015-05-20
宿州市徽腾知识产权咨询有限公司
View PDF4 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] According to literature reports, in recent years, people have paid more attention to the influence of substitution at different positions of the BODIPY matrix and the molecular space structure of derivatives on its photoelectric properties. Thi

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Meso-triphenylamine-substituted 3,5-aryl-modified boron dipyrromethene fluorophore derivatives and preparation method thereof
  • Meso-triphenylamine-substituted 3,5-aryl-modified boron dipyrromethene fluorophore derivatives and preparation method thereof
  • Meso-triphenylamine-substituted 3,5-aryl-modified boron dipyrromethene fluorophore derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Synthesis of BDP1

[0078]

[0079]In a 100ml two-necked bottle, add intermediate 5 (200mg, 0.24mmol), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborane (118mg, 0.58mmol) , sodium carbonate (101.76 mg, 0.96 mmol), 15 ml toluene / water (V:V=1:1). Switch on the argon replacement air device for about 5 minutes, quickly add tetrakis(triphenylphosphine)palladium (11 mg, 0.01 mmol), and reflux at a constant temperature of 90°C for 24 hours. Stop the reaction, cool to room temperature, dilute with water, extract with anhydrous diethyl ether (3×20ml), wash the organic phase with saturated brine (3×30ml), dry over anhydrous magnesium sulfate, filter, spin off the solvent, and the crude product is filtered through silica gel The dye BDP1 was obtained by column chromatography with a yield of 73%. 1 H NMR (600MHz, CDCl 3 )δ7.86(d, J=8.0Hz, 4H), 7.44(d, J=8.7Hz, 2H), 7.40(d, J=7.5Hz, 4H), 7.34(dd, J=8.6Hz, 6H) ,7.12(d,J=8.6Hz,4H),7.05(d,J=4.4Hz,4H),6.62(d,J=4.2Hz,2H),1.74(s,4H),1...

Embodiment 2

[0081] Synthesis of BDP2

[0082]

[0083] The synthesis method of dye BDP2 is similar to the synthesis of dye BDP1. Intermediate 5 (200mg, 0.24mmol), furan-2-boronic acid (65mg, 0.58mmol), sodium carbonate (101.8mg, 0.96mmol), 15ml toluene / water (V:V=1:1). Switch on the argon replacement air device for about 5 minutes, quickly add tetrakis(triphenylphosphine)palladium (11 mg, 0.01 mmol), and reflux at a constant temperature of 90°C for 24 hours. Yield 68%. 1 H NMR (600MHz, CDCl 3 )δ7.72(d, J=3.1Hz, 2H), 7.57(d, J=1.5Hz, 2H), 7.37(d, J=8.6Hz, 2H), 7.33(d, J=8.6Hz, 4H) ,7.11(d,J=8.6Hz,4H),7.05(d,J=8.6Hz,2H),7.00(d,J=4.4Hz,2H),6.97(d,J=4.4Hz,2H),6.64 (d,J=3.6Hz,2H),1.74(s,4H),1.43-1.21(m,12H),0.78(s,18H). 13 C NMR (151MHz, CDCl 3 )δ150.32,146.77,146.27,145.36,144.27,143.87,136.55,131.89,129.72,127.32,126.31,124.99,119.64,118.18,115.09,113.36,57.18,38.35,32.45,31.76,31.44.MALDI-TOF-MS,m / z:calcd for C 51 h 56 BF 2 N 3 o 2 :791.440,found:791.418[M]+.

Embodiment 3

[0085] Synthesis of BDP3

[0086]

[0087] In a 100ml two-necked flask, dissolve Intermediate 5 (200mg, 0.24mmol) in 20ml of toluene, add 2-(tributyltin-based)thiophene (215mg, 0.58mmol), tetrakis(triphenylphosphine)palladium (11mg, 0.01mmol ), reacted at a constant temperature of 90°C for 24h. Stop the reaction, cool to room temperature, wash with saturated brine (3×30ml), extract with dichloromethane (3×40ml), dry over anhydrous sodium sulfate, filter, spin off the solvent, and the crude product is subjected to silica gel column chromatography to obtain the dye BDP3 , yield 65%. 1 H NMR (600MHz, CDCl 3 )δ8.17(d, J=3.8Hz, 2H), 7.46(d, J=5.9Hz, 2H), 7.37(2, J=6.9Hz, 1H), 7.33(d, J=8.6Hz, 4H) ,7.18(t,J=5.0Hz,2H),7.11(d,J=8.6Hz,4H),7.05(d,J=8.7Hz,2H),6.95(d,J=4.3Hz,2H),6.80 (d,J=4.3Hz,2H),1.74(s,4H),1.42-1.21(m,12H),0.77(s,18H). 13 C NMR (151MHz, CDCl 3 )δ150.39,149.31,146.35,143.83,134.52,131.95,130.85,129.96,128.94,128.63,127.34,125.06,120.18,119.53,77.23,77.02,76.81,...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses meso-triphenylamine-substituted 3,5-aryl-modified boron dipyrromethene fluorophore derivatives (BODIPY) and a preparation method thereof. The meso-triphenylamine-substituted 3,5-aryl-modified boron dipyrromethene fluorophore derivative has a structure shown in a general formula I. The boron dipyrromethene fluorophore derivatives have an obvious red-shift phenomenon in comparison with ultraviolet absorption of BODIPY matrix; a fluorescence emission peak of the derivatives is close to a near-infrared region; and the synthesis method is simple, easy to control, and relatively high in yield, and has universality, so that the BODIPY dye can be efficiently synthesized and widely applied to the fields such as life science, analytical chemistry and environmental energy science, and especially can be applied to organic solar cells.

Description

Technical field: [0001] The invention relates to a boron fluoride complexed dipyrromethene (BODIPY) derivative modified by meso-position triphenylamines substituted for 3 and 5-position aryl groups and a preparation method thereof, and the derivatives can be widely used in life sciences and analytical chemistry , environmental energy science and other fields, especially as organic solar cell materials. Background technique: [0002] Boron fluoride complexed dipyrromethene (BODIPY) compound is a new type of organic dye developed in recent years and has received extensive attention. It is a compound formed by the complexation of dipyrromethane and boron trifluoride. The functional substitution of the BODIPY core and the introduction of different electron-withdrawing groups can greatly improve its luminescence performance and chemical properties. BODIPY derivative dyes have the advantages of excellent chemical stability, high photostability, large absorption coefficient, high ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07F5/02C09B57/00
CPCC07F5/022C09B57/00H10K85/322Y02E10/549
Inventor 赵鸿斌韩利芬廖俊旭彭敏王育才周伟男张文涛范素娟
Owner 宿州市徽腾知识产权咨询有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap