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Aggregation-induced emission pyranoquinoline red-light-emitting material and application thereof

A pyranoquinoline-based, aggregation-induced luminescence technology, applied in the field of fluorescent materials, can solve problems such as low yield, and achieve the effects of simple synthesis operation, large stokes shift value, and large molar absorption coefficient

Active Publication Date: 2022-01-04
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to obtain fluorescent materials with good properties, considerations need to be made: First, molecules with simple structures are preferred, since complex structures usually require complex and multiple synthetic steps with very low yields

Method used

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  • Aggregation-induced emission pyranoquinoline red-light-emitting material and application thereof
  • Aggregation-induced emission pyranoquinoline red-light-emitting material and application thereof
  • Aggregation-induced emission pyranoquinoline red-light-emitting material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 8-(Diethylamino)-2-imino-2H-pyrano[2,3-b]quinoline-3-carbonitrile (QPIC)

[0031] Add 3-(1H-benzo[d]imidazol-2-yl)-N,N-diethyl-2-imino-2H-pyrano[2,3-b]quinone sequentially into a 50mL one-necked bottle Lin-8-amine 1.00 g (2.6 mmol), malononitrile 0.25 g (3.9 mmol) and ethylene glycol monomethyl ether 20 mL. Reflux reaction for 3h (TLC detection). The reaction solution was cooled to room temperature, filtered under reduced pressure, recrystallized with methanol, and dried to obtain 0.80 g of a dark red solid with a yield of 70%. 1 H NMR (400MHz, DMSO-d 6 )δ:11.69(s,1H),8.55(s,1H),8.08(s,1H),7.52(d,J=8.8Hz,1H),6.78(dd,J=9.2,2.0Hz,1H), 6.44(s,1H),3.48(q,J=6.8Hz,4H),1.17(t,J=6.8Hz,6H). 13 C NMR (100MHz, DMSO-d 6 )δ: 160.81, 153.79, 153.16, 144.66, 142.25, 132.96, 116.25, 115.57, 114.98, 111.19, 110.43, 94.18, 73.70, 45.08, 12.96.

[0032] Adopt the step of above-mentioned embodiment 1, carry out adjustment optimization, specifically as follows:

[0033]

Embodiment 2

[0034] The preparation of embodiment 2 test solution

[0035] (1) Preparation procedure of stock solution:

[0036] Weigh the QPIC prepared in Example 1 and add it into a 10mL colorimetric tube, and prepare the concentration to be 1.0×10 - 3 mol / L chloroform solution, and then dilute QPIC by 10, 100, 1000, 10000 times respectively 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 -3 Add the mol / L QPIC solution into twelve 10mL colorimetric tubes, dilute to 10mL with different solvents, and make a concentration of 1.0×10 -6 mol / L solution, and measure the fluorescence quantum yield of QPIC, with rhodamine B as the standard reference.

[0037] (2) QPIC concentration-dependent test:

[0038] Take 2mL of QPIC chloroform solutions with different concentrations to test the ultraviolet absorption spectrum and fluorescence emission spectrum. In the ultraviolet-visible spe...

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Abstract

The invention discloses an aggregation-induced emission pyranoquinoline red light emitting material, and the structure of the aggregation-induced emission pyranoquinoline red light emitting material is 8-(diethylamino)-2-imino-2H-pyrano [2, 3-b] quinoline-3-nitrile (QPIC). According to the material, pyranoquinoline is used as a fluorophore, and a strong electron donating group diethylamino and an electron withdrawing group cyano are introduced to form a D-pi-A structure molecule. The red light material QPIC has the characteristics of large molar absorption coefficient, large stokes shift value, aggregation-induced emission (AIE), stability in a wide pH (2-11) range and the like. Besides, in a solution state, the material is sensitive to viscosity, can be used as a viscosity probe, and can be used as an enhanced fluorescent probe for rapidly measuring the viscosity of a solution in real time.

Description

technical field [0001] The invention relates to the technical field of fluorescent materials, in particular to a pyranoquinoline red-light material with aggregation-induced luminescence, a preparation method and application thereof. Background technique [0002] Organic molecular fluorescent materials are easy to modify. By changing various chromophores and introducing aromatic rings, ethylenic bonds and other functional groups, the conjugation and intermolecular interactions of the molecules can be changed, thereby changing the fluorescent properties of the molecules. Therefore, the development of organic molecular fluorescent materials is rapid and widespread. In order to obtain fluorescent materials with good properties, considerations need to be made: First, molecules with simple structures are preferred, because complex structures usually require complex and multiple synthesis steps with very low yields. Secondly, the actual application environment is an aqueous soluti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052C09B57/00C09K11/06G01N21/64G01N11/00
CPCC07D491/052C09B57/00C09K11/06G01N21/6428G01N11/00C09K2211/1033Y02B20/00
Inventor 但飞君唐倩郭涛
Owner CHINA THREE GORGES UNIV
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