Organic dye compounds with quinolinium ion skeleton structures and preparation method and application thereof

A technology of skeleton structure and organic dyes, which is applied in organic dyes, organic compounds/hydrides/coordination complex catalysts, organic chemistry, etc., can solve the problems of complex operation and difficulty in adjusting the luminescent properties of compounds, and achieve improvement The effect of electrical properties

Active Publication Date: 2018-04-27
THE HONG KONG POLYTECHNIC UNIV SHENZHEN RES INST
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] The object of the present invention is to provide an organic dye compound with a quinolinium ion skeleton structure and a preparation method thereof, aiming at solving the problem that the prior art does not have an organic dye compound with a quinolinium ion skeleton structure for organic chemical catalysts; and , the existing preparation methods of organic dye compounds, the operation is relatively complicated, and the compound is difficult to realize the problem that the luminescence properties can be adjusted

Method used

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  • Organic dye compounds with quinolinium ion skeleton structures and preparation method and application thereof
  • Organic dye compounds with quinolinium ion skeleton structures and preparation method and application thereof
  • Organic dye compounds with quinolinium ion skeleton structures and preparation method and application thereof

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preparation example Construction

[0033] And, the embodiment of the present invention provides a method for preparing an organic dye compound with a quinolinium ion skeleton structure, comprising the following steps:

[0034] S01. Provide diazonium salts 1a, 1b, and 1c with quinoline structures shown in formulas 1a, 1b, and 1c, trimethylsilyl alkyne derivatives and monovalent gold complexes shown in formula 2, respectively;

[0035] S02. Dissolve the 1a, 1b, and 1c respectively in an organic solvent, add the trimethylsilyl alkyne derivative 2, use the monovalent gold complex as a catalyst, and perform catalysis under visible light irradiation and room temperature conditions The cycloaddition reaction generates the general structural formula as the quinolinium ion skeleton structure organic dye compound shown in the following structures I, II, and III, and the reaction formula is as follows respectively,

[0036]

[0037] In the above step S01, the diazonium salts 1a, 1b, and 1c with quinoline structures rep...

Embodiment 1

[0058] Embodiment 1: the synthesis of organic dye I-1

[0059]

[0060] With quinoline structure diazonium salt 1a (0.6mmol), (4-methoxyphenylethynyl) trimethylsilane 2a (0.5mmol), Ph 3 PAuCl (0.05 mmol) and acetonitrile (5 mL) were mixed in a 20 mL glass test tube and sealed with a rubber stopper. The air in the test tube was removed by the freeze-thaw pump circulation method and flushed with nitrogen. After the mixture in the test tube returned to room temperature, the test tube was placed under the irradiation of a blue LED light source to react for 16 hours. After the reaction was completed, the solvent was removed, and the product was obtained as an orange solid after chromatographic separation, and the yield was 69%.

[0061] 1 H NMR (400MHz, MeOD) δ9.12(d, J=9.0Hz, 1H), 9.02(d, J=8.5Hz, 1H), 8.92(d, J=8.9Hz, 1H), 8.43(d, J =8.2Hz,1H),8.24(d,J=7.2Hz,1H),8.17(t,J=7.6Hz,1H),8.04(t,J=7.6Hz,1H),7.72(m,2H), 7.48-7.32(m,3H),7.06(d,J=8.7Hz,2H),3.90(s,3H),0.14(s,9H).

...

Embodiment 2

[0063] Embodiment 2: the synthesis of organic dye 1-2

[0064]

[0065] Refer to Example 1 for specific operation, yellow solid, yield 68%.

[0066] 1 H NMR (400MHz, MeOD) δ9.16(d, J=9.0Hz, 1H), 9.04(d, J=8.4Hz, 1H), 8.94(d, J=8.9Hz, 1H), 8.46(d, J =8.3Hz, 1H), 8.25(d, J=7.1Hz, 1H), 8.18(t, J=7.3Hz, 1H), 8.06(t, J=7.7Hz, 1H), 7.77-7.66(m, 2H ),7.66-7.58(m,1H),7.52(m,4H),7.39-7.26(m,1H),0.12(s,9H).

[0067] 13 C NMR(101MHz,MeOD)δ150.61,147.87,142.81,139.97,138.26,137.85,135.24,134.94,133.12,131.88,131.20,130.51,130.26,130.19,129.92,127.91,126.40,126.28,119.46,1.88.

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Abstract

The invention provides organic dye compounds with quinolinium ion skeleton structures. The organic dye compound comprises a quinolinium ion skeleton structure, a trimethylsilyl group bonded to the quinolinium ion skeleton structure through a carbon-silicon single bond and a substituent group connected to the quinolinium ion skeleton structure through a carbon-carbon bond. The organic dye compoundswith quinolinium ion skeleton structures have general structural formulas I, II and III.

Description

technical field [0001] The invention belongs to the technical field of organic dyes, and in particular relates to an organic dye compound with a quinolinium ion skeleton structure and a preparation method and application thereof. Background technique [0002] Due to the characteristics of high sensitivity, adjustable properties and strong practicability, the phenomenon of luminescence (fluorescence or phosphorescence) of organic molecules has been widely used in the fields of synthetic chemistry, material science, chemical biology and biomedical science, and has become an academic research field. , an indispensable means or tool in technology development and product manufacturing. Therefore, designing and synthesizing new organic dyes and studying their optical properties and application prospects have become a hot field of scientific research in recent years. In this field, most of the current research focuses on the design and modification of derivatives of existing lumin...

Claims

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Application Information

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IPC IPC(8): C09B57/00C07F7/10C09K11/06B01J31/02C07D295/192
CPCC09K11/06C07D295/192C07F7/0814C07F7/083C09B57/00B01J31/0275C09K2211/1029B01J35/39
Inventor 黄文健邓杰仁励晋谦
Owner THE HONG KONG POLYTECHNIC UNIV SHENZHEN RES INST
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