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Application of a compound as an electrochemiluminescent material

A technology of luminescent materials and compounds, applied in luminescent materials, organic chemistry, electrical excitation analysis, etc., can solve the problems of high price and low toxicity, and achieve the effects of reducing the use of organic solvents, reducing synthesis costs, and improving luminous efficiency

Active Publication Date: 2020-04-21
JIANGHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] For ECLDs devices, the typical luminescent material that has been confirmed is polypyridine transition metal complex. Although this luminescent material has good performance, it is expensive, and the synthesis process involves many solvents that are harmful to the environment. More importantly, The metal part in it restricts the application of such compounds in fields with high requirements for biocompatibility and toxicity, such as biological detection. Therefore, it is necessary to develop new ECL materials with low toxicity, good biocompatibility, and low cost. The synthesis method is environmentally friendly and has good luminous efficiency; in addition, it is necessary to develop matching electrolytes, buffer ions and co-reactants

Method used

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  • Application of a compound as an electrochemiluminescent material
  • Application of a compound as an electrochemiluminescent material
  • Application of a compound as an electrochemiluminescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]

[0040]In a 250mL round bottom flask, first add 0.5-0.1e.q. of L-proline (preferably 230mg, 0.2mmol) and 1.0-1.5e.q. of malononitrile (preferably 793mg, 12mmol) to dissolve completely, then add 1.0e.q. Benzaldehyde (preferably 1.06g, 10mmol), 1.0~1.2e.q. of 2-amino-5-picoline (preferably 1.296g, 12mmol), placed on an oil bath at 90°C for reaction, TLC (thin layer chromatography ) to complete the reaction for about 8 hours. Post-treatment purification: adding dichloromethane (20mL×3) for extraction, washing with saturated NaCl solution (20mL×1), separating and combining the organic phase and adding anhydrous sodium sulfate for drying. Remove the solvent, separate and purify with silica gel column chromatography, the range of V (petroleum ether): V (ethyl acetate) is 10:1 to 1:1, preferably, V (petroleum ether): V (ethyl acetate) = 3 :1, to obtain pure yellow powder.

[0041] Compound I-1 is tested by proton nuclear magnetic spectrum:

[0042] 1 H NMR (400MHz, CDC...

Embodiment 2

[0044]

[0045] In a 50mL round bottom flask, add compound I-1 (970mg, 3.73mmol) and 15mL of acetic anhydride, heat to 150°C for reaction, TLC (thin layer chromatography) detects that the reaction is complete for about 3.5h. Carry out post-processing purification: remove acetic anhydride, separate and purify with silica gel column chromatography, the scope of V (petroleum ether): V (ethyl acetate) is 1:1 to 1:10, preferred [V (petroleum ether) in the present embodiment ): V (ethyl acetate) = 1:10] to obtain a yellow powder.

[0046] The proton nuclear magnetic spectrum of compound 1-2 is as follows:

[0047] 1 H NMR (400MHz, CDCl 3 )δ9.09(s,1H),7.99(d,J=7.1Hz,2H),7.85(dd,J=8.9,1.6Hz,1H),7.73(d,J=8.9Hz,1H),7.60- 7.42(m,3H),7.26(s,1H),2.47(d,J=35.9Hz,6H).

Embodiment 3

[0049]

[0050] In a 250mL round bottom flask, first add 0.05-0.3e.q. of L-proline (preferably 230.6mg, 2.0mmol) and 1.0-1.5e.q. of malononitrile (preferably 7-93.2mg, 12mmol) to dissolve completely, then add 1.0e.q of 4-bromo-benzaldehyde (1.85g, 10mmol), 1.0~1.5e.q. of 2-amino-5-picoline (preferably 1.296g, 12mmol), placed on a 90°C oil bath for reaction, TLC ( Thin-layer chromatography) detects that the reaction is complete for about 8 hours. Post-treatment purification: adding dichloromethane (20mL×3) for extraction, washing with saturated NaCl solution (20mL×1), separating and combining the organic phase and adding anhydrous sodium sulfate for drying. Remove the solvent, separate and purify with silica gel column chromatography, the range of V (dichloromethane): V (ethyl acetate) is 100:1 to 5:1, preferably, V (dichloromethane): V (ethyl acetate) =30:1, a yellow powder was obtained. The yield of this reaction reaches 56%.

[0051] Compound II-1 is tested by H NMR sp...

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Abstract

The invention provides an application of a compound as an ECL material. The compound does not contain metal, has low toxicity, good biocompatibility, low cost, an environmentally friendly synthesis method and good luminous efficiency as an ECL. In the application of the compound as an ECL material, the compound has a specific structural formula that does not contain metal. Specifically, the compound is used as an ECL material, together with a co-reactant, a double electrode and a supporting electrolyte to construct an electrochemiluminescent device. The compound of the present invention can realize the construction of ECL material without metal, which greatly reduces the synthesis cost and has good biocompatibility; the compound of the present invention has good luminous efficiency as an ECL material; the compound of the present invention synthesizes The method and process are simple, water is used as the main synthesis environment in the synthesis process, and the process is green to realize environmental friendliness.

Description

technical field [0001] The invention relates to the field of luminescent materials, in particular to the application of a compound as an electrochemiluminescence material. Background technique [0002] Electrochemical Luminescent Material ECL (electrochemiluminescence) material is a widely used luminescent material, which has been used in LECs light-emitting devices (light-emitting electrochemical cells). In 2018, the literature reported ECLDs (electrochemiluminescence devices) devices built with ECL materials as the core. The basic configuration and core mechanism of ECLDs are substantially different from LECs in the traditional sense. Therefore, ECLDs are regarded as an independent type of light-emitting device and have won people's attention. The simplest structure of LECs consists of a substrate, an active layer (including ECL materials) and a top metal electrode; the principle of light emission is to rely on continuous transitions to conduct different charges direction...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06G01N21/66
CPCC07D471/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044G01N21/66
Inventor 王洪波周瑞雪程俊
Owner JIANGHAN UNIVERSITY
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