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Fluorene and carbazole bridging-based A-D-A type double-center BODIPY (boron-dipyrrolemethene) derivative and preparation method for same

A technology of A-D-A and dipyrrole methine is applied in the field of organic optoelectronic materials, which can solve the problems of single molecular structure, not many reports, and few samples.

Inactive Publication Date: 2016-10-12
DONGGUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The application of BODIPY small molecule materials in fluorescent dyes has been well studied, while the research in other fields of organic optoelectronics is limited by the single molecular structure and too few samples, and there are not many reports.
For example, in the field of solar cells, there are less than 10 reported small molecule solar cell materials based on BODIPY derivatives, and most of their energy conversion efficiencies are lower than 3%.

Method used

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  • Fluorene and carbazole bridging-based A-D-A type double-center BODIPY (boron-dipyrrolemethene) derivative and preparation method for same
  • Fluorene and carbazole bridging-based A-D-A type double-center BODIPY (boron-dipyrrolemethene) derivative and preparation method for same
  • Fluorene and carbazole bridging-based A-D-A type double-center BODIPY (boron-dipyrrolemethene) derivative and preparation method for same

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Experimental program
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Embodiment

[0048] (1) Synthesis of Intermediate 1

[0049] Add p-hydroxybenzaldehyde (12.5g, 0.1mol), potassium carbonate (16.5g, 0.12mol), bromo-n-octane (23.2g, 0.12mol) and acetonitrile (150mL) successively in a 500mL round bottom flask, The reaction temperature was controlled at 80° C. for 10 h with magnetic stirring. After the reaction was completed, the solid residue was removed by filtration with a sand core funnel, the filtrate was extracted with ethyl acetate, washed with saturated brine, and dried with anhydrous magnesium sulfate to obtain a crude product. The crude product was purified by silica gel (200-300 mesh) column chromatography [eluent, V (petroleum ether): V (ethyl acetate) = 10:1] to obtain yellow liquid intermediate 1, 22.2 g, yield 95%. 1 H NMR (600MHz, CDCl 3 ), δ: 9.82 (d, J = 1.4Hz, 1H), 7.77 (dd, J = 8.7, 1.5Hz, 2H), 6.93 (dd, J = 8.7, 1.5Hz, 2H), 3.97 (td, J = 6.6,1.6Hz,2H),1.82-1.65(m,2H),1.50-1.35(m,2H),1.35-1.18(m,10H),0.87(m,3H). 13 C NMR (151MHz, CDC...

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Abstract

The invention discloses a fluorene and carbazole bridging-based A-D-A type double-center BODIPY (boron-dipyrrolemethene) derivative and a preparation method for the same. A novel double-center BODIPY derivative I containing different bridging groups such as fluorene and carbazole is obtained by substituting position 2 of BODIPY and coupling an electron-donating unit such as 9,9-dialkylfluorene and 9-alkylcarbazole to a BODIPY receptor unit. After fluorene and different carbazole modification points are introduced into a double-center BODIPY structure, the ultraviolet absorption of the derivative has an obvious red shift, the HOMO (highest occupied molecular orbital) energy level is lower (-5.43 to -5.51eV), and the derivative has high stability. A synthesis method for the fluorene and carbazole bridging-based A-D-A type double-center BODIPY derivative is simple, and the fluorene and carbazole bridging-based A-D-A type double-center BODIPY derivative can be efficiently synthesized and widely applied to the field of organic photoelectronic materials.

Description

technical field [0001] The invention relates to an A-D-A double-center boron fluoride complexed dipyrromethene derivative based on fluorene and carbazole bridging and a preparation method thereof. The derivative can be widely used in the field of organic optoelectronic materials. Background technique [0002] Boron fluoride complexed dipyrromethene (4,4′-Difluoro-4-bora-3a,4a-diaza-sindacene, referred to as BODIPY) fluorescent dyes have good photostability, high molar absorptivity and high oxidation Potential, a very potential small molecule donor material, has been used in fluorescent dyes, organic solar cell materials, luminescent materials and other fields. [0003] The application of BODIPY-like small molecule materials in fluorescent dyes has been well studied, while the research in other fields of organic optoelectronics is limited by the single molecular structure and too few samples, and there are not many reports. For example, in the field of solar cells, there are...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09B23/12
CPCC07F5/022C09B23/12
Inventor 廖俊旭赵鸿斌徐勇军韩利芬张文涛彭敏戴康徐陈灿奎
Owner DONGGUAN UNIV OF TECH
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