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Triazolyl quinoline copper complex with AIE properties and preparation method thereof

A technology of triazolyl quinoline copper and complexes, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of unfavorable fluorescence emission, no emission, and reduced luminous efficiency, and achieve good solid fluorescence, intensity big effect

Inactive Publication Date: 2020-10-27
FUYANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

That is, most organic light-emitting materials can have very good light-emitting properties in solution, but in the aggregated state, they often show a phenomenon that the luminous efficiency is greatly reduced or even does not emit light. The main reason for this phenomenon is the interaction between molecules. Species that cause non-radiative energy conversion or create unfavorable fluorescence emissions

Method used

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  • Triazolyl quinoline copper complex with AIE properties and preparation method thereof
  • Triazolyl quinoline copper complex with AIE properties and preparation method thereof
  • Triazolyl quinoline copper complex with AIE properties and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0041]Synthesis of 4-(1-1,2,4-triazolyl)benzaldehyde (Intermediate Ⅰ):

[0042] Add 6.91g (100mmol) of triazole, 14.86g (107.5mmol) of potassium carbonate and 80mL of DMSO into a 250mL three-necked flask equipped with a magnet, and add 5 drops of Aliquat336 dropwise while stirring, and keep the temperature up to 90°C for 5min; 12.9 mL of p-fluorobenzaldehyde (120 mmol) was slowly added dropwise into the flask, and the reaction was stopped after stirring at 80° C. for 24 h. Filtrate while it is hot, pour the filtrate into 500 mL of ice water, stir, a large amount of solids precipitate out, leave to separate layers, and filter with suction to obtain 13.03 g of white flocculent solids, yield 75.2%, m.p.150-151°C. 1 H NMR (400MHz, DMSO-d 6 , TMS) δ (ppm): 10.62 (s, 1H), 9.53 (s, 1H), 8.31 (s, 1H), 8.17 (s, 2H), 8.12 (s, 2H).

[0043] Synthesis of (E)-2-[2-(4-(1-1,2,4-triazolyl)phenyl)vinyl]-8-acetoxyquinoline (intermediate Ⅱ):

[0044] Weigh 5.73g (36mmol) of 2-methyl-8-hydroxy...

Embodiment 2

[0056] Absorption Spectrum Theoretical Calculation (TD-DFT Method) of Embodiment 2 Ligand L

[0057] The linear absorption calculation of compound L was carried out using TD-DFT theory, using the B3LYP / 6-311G(d,p) method, the solvent was THF, and its geometric structure was optimized (the molecular ground state geometry of L was obtained directly from the single crystal data Acquisition), the calculations involved are all completed on the Gaussian09 program package. The relevant calculation results are listed in Table 2, and the molecular orbital diagram of the front line is shown in Figure 6 shown.

[0058] Table 2 Theoretical calculation of linear absorption, excitation energy, oscillator strength and transition mode of ligand L

[0059]

[0060] The data obtained by theoretical calculation (Table 2) and the molecular orbital diagram ( Figure 6 ) It can be seen that the maximum absorption peaks of compound L in the low-energy region are at 394.86nm, which can be attr...

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Abstract

A triazolyl quinoline copper complex having an AIE property and a preparing method thereof are disclosed, belonging to the technical field of metal organic complexes. The triazolyl-containing 2-substituted-8-hydroxyquinoline copper complex is synthesized, and is characterized by IR spectrum, 1H NMR, <13>C NMR and element analysis, and optical properties of a ligand and the complex are studied. Theaggregation induced emission (AIE) intensity of the complex is highest when the complex is in a CH3CN / water solvent mixture and the water content is 60%, and a solid-state fluorescence property is good.

Description

technical field [0001] The invention belongs to the technical field of metal-organic complexes, and in particular relates to a triazolylquinoline copper complex with AIE properties and a preparation method thereof. Background technique [0002] "Aggregation-induced emission" (aggregation-induced emission, AIE) was first proposed by Academician Tang Benzhong of Hong Kong University of Science and Technology in 2001. The so-called aggregated luminescence means that the fluorescent molecules have almost no fluorescence in the single molecule state, but the luminous efficiency is greatly improved in the aggregated state. This property is opposite to the aggregation-caused quenching (ACQ) property of traditional fluorescent molecules. That is, most organic light-emitting materials can have very good light-emitting properties in solution, but in the aggregated state, they often show a phenomenon that the luminous efficiency is greatly reduced or even does not emit light. The main...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/10C09K11/06
CPCC07D401/10C09K11/06C09K2211/188
Inventor 刘杰苗慧乔瑞刘昭第
Owner FUYANG NORMAL UNIVERSITY