Near infrared absorption organic dyestuff based on alkynyl triphenylamine and perylene diimide and preparation method and application thereof

A technology of perylene diimide and alkynyl triphenylamine, which is applied in the directions of organic dyes, chemical instruments and methods, azo dyes, etc., can solve problems such as limited application, and achieve the effects of excellent light absorption performance, less pollution and simple steps.

Inactive Publication Date: 2018-07-06
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the ultraviolet-visible absorption spectrum of the synthesized product is only between 350 and 750 nm, which limits its application in the field of optoelectronics

Method used

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  • Near infrared absorption organic dyestuff based on alkynyl triphenylamine and perylene diimide and preparation method and application thereof
  • Near infrared absorption organic dyestuff based on alkynyl triphenylamine and perylene diimide and preparation method and application thereof
  • Near infrared absorption organic dyestuff based on alkynyl triphenylamine and perylene diimide and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083]

[0084] The 100mL reaction flask was evacuated and nitrogen protection, 300mg monobromoperylene diimide (1), 90mg monoalkynyltriphenylamine (2), 20mL anhydrous toluene, 5ml diisopropylamine, 100mg tetrakis (triphenyl Phosphine) palladium and 20 mg cuprous iodide were added to the reaction flask, the oil bath was turned on and heated to 80° C., the reaction was completed after 12 hours, and the obtained crude product was separated and purified by thin-layer chromatography to obtain 0.32 g of blue-purple product (3). E. LUMO =-3.70eV,E HOMO =-5.30eV, the yield was 85%.

Embodiment 2

[0086]

[0087] The 100ml reaction flask was evacuated and protected by nitrogen gas, 300mg monobromoperylene diimide (1) and 99mg dimethoxyalkynyltriphenylamine (4), 20mL anhydrous toluene, 5ml diisopropylamine, Add 100mg tetrakis(triphenylphosphine)palladium and 20mg cuprous iodide into the reaction flask, turn on the oil bath and heat to 80°C, the reaction ends after 12 hours, and the obtained crude product is separated and purified by thin-layer chromatography to obtain the blue-purple product ( 5) 0.29g, E LUMO =-3.71eV,E HOMO =-5.29eV, the yield was 80%.

Embodiment 3

[0089]

[0090] The 100mL reaction flask was evacuated and protected by nitrogen, weighed 306mg of bisbromoperylenediimide (6) and 186mg of alkynyltriphenylamine (2), 20mL of anhydrous toluene, 5ml of diisopropylamine, 100mg of tetrakis(triphenylamine) Phenylphosphine)palladium and 20mg of cuprous iodide were added to the reaction flask, and the oil bath was turned on to heat to 80°C. The reaction was completed after 12 hours. The obtained crude product was separated and purified by thin-layer chromatography to obtain 0.28g of blue-purple product (7) ,E LUMO =-4.0eV, E HOMO =-5.56eV, the yield was 68%.

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Abstract

The invention discloses a near infrared absorption organic dyestuff based on alkynyl triphenylamine and perylene diimide and a preparation method and application thereof. The organic dyestuff takes alkynyl triphenylamine and perylene diimide as raw materials, and is prepared by adopting Sonogashira reaction; the preparation method is simple and mild in condition, and simultaneously, compared withperylene diimide, the prepared and obtained organic dyestuff obviously changes the distribution of LUMO and HOMO of perylene diimide. The energy levels of LOMO and HOMO of perylene diimide and the energy level difference between LOMO and HOMO of perylene diimide are changed, so that the UV absorption spectrum of the organic dyestuff is of great red shift and almost cover the whole visible light region, and the applied range in the photoelectric field is effectively improved.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to an organic dye based on the near-infrared absorption of alkynyl triphenylamine and perylene diimide, a preparation method and application thereof. Background technique [0002] Perylene diimide and its derivatives are planar conjugated fused-ring macromolecules with excellent physical and chemical properties. Because of its unique photophysical and electrochemical properties and excellent solubility in common organic solvents, it is widely used in organic solar energy conversion, photoconductors, signal amplification, laser dyes, fluorescent probes, fluorescent aggregates, liquid crystal materials, etc. It has broad application prospects. [0003] Triphenylamine and its derivatives have unique free radical properties. There are three benzene rings arranged at a certain angle around the nitrogen atom, which eliminates the tension in the free radical...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C07D471/06C07D491/16
CPCC07D471/06C07D491/16C09B57/00
Inventor 李刚李丹丹王帅花张羽王苒唐波
Owner SHANDONG NORMAL UNIV
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