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Preparation method and application of a kind of terpyridine compound and metal complex thereof

A technology of metal complexes and terpyridines, applied in the direction of zinc organic compounds, chemical instruments and methods, applications, etc., can solve the problems of short duration, light stimulus response, transmission, etc., and achieve the effect of mild conditions and simple synthesis steps

Active Publication Date: 2020-11-17
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The recently developed water-jet ink-free printing provides us with a new idea, but it requires light stimulus response, and the duration is short, which is not conducive to the transmission of information.

Method used

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  • Preparation method and application of a kind of terpyridine compound and metal complex thereof
  • Preparation method and application of a kind of terpyridine compound and metal complex thereof
  • Preparation method and application of a kind of terpyridine compound and metal complex thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: Terpyridine compound L 1 preparation

[0036] Synthetic route such as figure 1 As shown, the specific steps are as follows:

[0037] Step 1, in the DMSO solvent system, react carbazole, bromohexane and 50% sodium hydroxide aqueous solution in a molar ratio of 1:2:2 at 50°C for 8 hours, first distill under reduced pressure, extract with water and ethyl acetate, and obtain The organic layer was then washed with anhydrous Na 2 SO 4 Dried, spin-dried, separated and purified to obtain compound 1, its structural formula is:

[0038]

[0039] Step 2, in a dichloromethane solvent system, react compound 1 and NBS at a molar ratio of 1.2:1 at 25°C for 8 hours, filter, and wash with dichloromethane several times to obtain compound 2, whose structural formula is:

[0040]

[0041] Step 3, under the condition of nitrogen protection, in the dry diisopropylamine solution system, p-bromobenzaldehyde, trimethylethynyl silicon, cuprous iodide and tetrakistripheny...

Embodiment 2

[0053] Embodiment 2: the preparation of multi-color copying paper

[0054] (1) Coat the polyethylene glycol-polypropylene glycol-polyethylene glycol (PEG-PPG-PEG) solution that is dissolved in dichloromethane on the filter paper, dry, as the first layer;

[0055] (2) The terpyridine compound L dissolved in dichloromethane 1 Apply the PEG-PPG-PEG mixture evenly on the first layer as the second layer;

[0056] (3) Coat the second layer with PEG-PPG-PEG as the third layer to make multi-color copy paper.

Embodiment 3

[0057] Example 3: Terpyridine Metal Complex L 1 -M preparation

[0058] A luminescent terpyridine metal complex, the structure consists of two parts: one part is terpyridine compound L 1 , and the other part is a different metal salt.

[0059] Terpyridine Metal Complex L 1 -Synthesis of M: the metal salt is directly combined with the corresponding terpyridine compound L 1 Stir in methanol solution at room temperature for 2h. L 1 The general structural formula of -M is as follows:

[0060]

[0061] Where M=Fe(NO 3 ) 3 , Co(NO 3 ) 2 , Ni(NO 3 ) 2 , FeCl 2 , FeCl 3 , CuCl 2 , Zn(CH 3 COO) 2 , ZnCl 2 , Zn(ClO 4 ) 2 and Zn(NO 3 ) 2 .

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Abstract

The invention discloses preparation methods and applications for a terpyridine compound and a terpyridine metal complex. The preparation method for the terpyridine compound comprises the following steps: subjecting carbazole, bromohexane and a sodium hydroxide aqueous solution with the concentration of 50% to a substitution reaction in a DMSO solvent system at 50 DEG C; subjecting a compound 1 andNBS to a regioselective bromination reaction in a dichloromethane solvent system at 25 DEG C; subjecting bromobenzaldehyde, trimethylsilylacetylene, cuprous iodide and (beta-4)-platinum to a Sonogashira coupling reaction in a nitrogen gas environment and a dry diisopropylamine solution system at 80 DEG C; subjecting a compound 2, a compound 3, cuprous iodide and (beta-4)-platinum to a Sonogashiracoupling reaction in a nitrogen gas environment and a dry diisopropylamine and tetrahydrofuran solution system; and subjecting an alkyne-containing compound 4, diacylpyridine and potassium hydroxideto a Krohnke intermediate cyclization process reaction in an ethanol solvent system at 25 DEG C. The preparation method for the terpyridine compound provided by the invention has simple synthetic steps and mild conditions, and realizes multi-color printing and encrypted printing under visible sunlight.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and in particular relates to a preparation method of a terpyridine compound and a metal complex thereof and its application in printing and color development. Background technique [0002] Rewritable paper has attracted attention due to potential environmental advantages such as forest conservation, pollution reduction, energy conservation, and resource sustainability. However, effective strategies to achieve multicolor printing on rewritable paper are still lacking, which hinders its real-life application. [0003] In recent years, stimuli-responsive luminescent materials have become a research hotspot for scientists in recent years, and various materials that respond to external stimuli have been developed. The recently developed water-jet ink-free printing provides us with a new idea, but it requires light stimulus response and the duration is short, which i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C07F3/06C09K11/06C09K9/02C09D11/38D21H19/20D21H19/42D21H19/82
CPCC07D401/14C07F3/003C09D11/38C09K9/02C09K11/06C09K2211/1029C09K2211/187C09K2211/188D21H19/20D21H19/42D21H19/82
Inventor 赵强佘鹏飞马云刘淑娟黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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