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Fused heteroaromatic organic luminescent material and its preparation method and application

A luminescent material and organic technology, applied in luminescent materials, material analysis through optical means, organic chemistry, etc., to achieve high yield, overcome low luminous efficiency, and large molar absorption coefficient

Active Publication Date: 2022-04-12
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Currently, there are few reports on fluorescent probes for extremely acidic (pH<4)

Method used

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  • Fused heteroaromatic organic luminescent material and its preparation method and application
  • Fused heteroaromatic organic luminescent material and its preparation method and application
  • Fused heteroaromatic organic luminescent material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] N11-(Diethylamino)benzo[g]benzo[4,5]imidazo[1,2-a][1,8]naphthyridine-6-carbonitrile (NBC)

[0036] Add 1.00 g (3.8 mmol) of 2-chloro-7-(diethylamino) quinoline-3-carbaldehyde, 0.50 g (3.2 mmol) of 2-cyanomethylbenzimidazole and N,N- Add 10 mL of dimethylformamide, then add 0.5 mL of pyridine, heat and stir. The resulting mixture was then stirred at 85 °C until the reaction was complete (checked by TLC). Naturally cooled to room temperature, 30 mL of water was added to the reaction solution, and an orange solid was precipitated, filtered under reduced pressure, silica gel column chromatography, and eluted with petroleum ether:ethyl acetate=5:1 to obtain 1.05 g of an orange solid with a yield of 70 %. 1 H NMR (400MHz, DMSO-d6) δ: 9.36 (d, J = 8.0Hz, 1H), 8.74 (d, J = 23.2Hz, 1H), 8.02-7.93 (m, 2H), 7.65–7.57 (m, 2H), 7.36(dd, J=9.2, 2.0Hz, 1H), 7.20(s, 1H), 3.64(q, J=7.2Hz, 4H), 1.26(t, J=6.8Hz, 6H). 13 C NMR(100MHz,DMSO)δ:152.07,150.80,146.70,146.27,143.97,140.92,139...

Embodiment 2

[0039] The preparation of embodiment 2 test solutions

[0040] (1) Preparation procedure of stock solution:

[0041] Weigh the NBCs prepared in Example 1 and add them into 10mL colorimetric tubes to prepare a concentration of 1.0×10 -3mol / L chloroform solution was used as the stock solution, and then the NBC stock solution was diluted 10, 100, 1000, and 10000 times to prepare a concentration of 1.0×10 -4 mol / L, 1.0×10 -5 mol / L, 1.0×10 -6 mol / L, 1.0×10 -7 mol / L chloroform solution. Take 10 μL concentration as 1.0×10 -5 Add the mol / L NBC solution into twelve 10mL colorimetric tubes, dilute to 10mL with different solvents, and make a concentration of 1.0×10 -6 mol / L solution to measure the fluorescence quantum yield of NBC, with rhodamine B as the standard reference.

[0042] (2) NBC concentration-dependent test:

[0043] Take 2mL NBC chloroform solutions with different concentrations to test the UV-Vis absorption spectrum and fluorescence emission spectrum. Such as im...

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Abstract

The invention discloses a novel condensed heteroaromatic ring organic light-emitting material, the structure of which is 11-(diethylamino)benzo[g]benzo[4,5]imidazo[1,2-a][1, 8] Naphthyridine-6-carbonitrile (NBC). This material is prepared by one-pot method using 2-chloro-7-(diethylamino)quinoline-3-formaldehyde and 2-cyanomethylbenzimidazole as raw materials. In solution, NBC has large molar absorption coefficient, high fluorescence quantum yield, and large stokes shift value. It is sensitive to solvent, environmental pH, and viscosity. It can be used as a pH and viscosity probe to measure pH and solution viscosity in real time and quickly. In the solid state, the emission wavelength of NBC is in the near-infrared region, and the luminous efficiency is high. NBC has good luminescence properties in both solution and solid state, and the dual-efficiency organic materials realize the multi-functionalization of applications.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials, in particular to a condensed heteroaromatic organic luminescent material and its preparation method and application. Background technique [0002] It shows excellent luminescent performance in a well-dispersed solution, but in a higher concentration solution or in an aggregated state, the fluorescence is weakened or even completely extinguished, that is, the aggregation-caused quenching effect (Aggregation-Caused Quenching, ACQ) organic Luminescent materials occupy an important position in the fields of chemistry, biology, and materials, and have attracted much attention. Traditional organic light-emitting materials show excellent luminescent performance in a well-dispersed solution, but in a higher concentration solution or in an aggregated state, the fluorescence is weakened or even completely quenched, that is, the aggregation quenching effect (ACQ). This greatly limits ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/14C09K11/06G01N21/64
CPCC07D471/14C09K11/06G01N21/6428C09K2211/1059
Inventor 但飞君唐倩郭涛
Owner CHINA THREE GORGES UNIV
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