Metal iridium-carbene complex with photocatalytic performance as well as preparation method and application thereof

A carbene complex, metal iridium technology, applied in indium organic compounds, platinum group organic compounds, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of difficult industrial production, harsh reaction conditions, etc. Catalytic effect, high photocatalytic efficiency

Inactive Publication Date: 2020-08-18
CHANGZHOU INST OF TECH
View PDF0 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the technical problems of harsh reaction conditions and difficult industrial production in the traditional addition reaction of terminal alkyne compounds and isatin derivatives, a metal ir...

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Metal iridium-carbene complex with photocatalytic performance as well as preparation method and application thereof
  • Metal iridium-carbene complex with photocatalytic performance as well as preparation method and application thereof
  • Metal iridium-carbene complex with photocatalytic performance as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0039] Another aspect of the embodiments of the present invention provides a method for preparing the above metal iridium-carbene complex with photocatalytic properties, comprising the following steps:

[0040] (1) Synthesis of carbene precursor pyridine-imidazolium bromide:

[0041]

[0042] Mix N-(2,4,6-trimethylphenyl)imidazole and 2-bromopyridine as shown in the structure of formula I, seal, heat up and stir the reaction under solvent-free conditions, cool to room temperature after the reaction, and obtain The first crude product, the first crude product is taken out and washed with an ether solvent and suction filtered to obtain the carbene precursor pyridine-imidazolium bromide shown in the structure of formula II;

[0043] (2) Synthesis of metal iridium-carbene complexes:

[0044]

[0045] i) Dissolve the carbene precursor pyridine-imidazolium bromide salt prepared in step (1) in a halogenated hydrocarbon solvent, then add silver oxide solids, and react for 1 h a...

Embodiment 1

[0059] (1) Synthesis of carbene precursor pyridine-imidazolium bromide:

[0060]

[0061] In a high-temperature reaction tube equipped with a magnetic stirring bar, add 18.6 grams (100 mmol) of N-(2,4,6-trimethylphenyl) imidazole solid as shown in the structure of formula I, and then add 16.5 grams (105 mmol) of 2-bromopyridine, mix well, then seal the tube, heat up to 180°C, melt and stir for 18 hours under solvent-free conditions, cool to room temperature after the reaction, and obtain the first crude product, scrape the first crude product Take it out and put it into a centrifuge tube, add diethyl ether and shake and wash the first crude product 5 times (30mL×5 times each time), filter with suction, and obtain 30.9 grams of milky white powder after drying, which is the carbene precursor shown in the structure of formula II Pyridine-imidazolium bromide, yield 90wt%;

[0062] The reaction of step (1) is a solvent-free reaction. At high temperature, the N-(2,4,6-trimethylp...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to a metal iridium-carbene complex with photocatalytic performance as well as a preparation method and application thereof, the molecular formula of the metal iridium-carbene complex is C34H36Cl2IrN6PF6, and the metal iridium-carbene complex is a mononuclear-hexadentate coordination compound of a monoclinic system and belongs to a P21/c space group; the preparation method comprises the following steps: firstly, preparing carbene precursor pyridine-imidazole bromide from N-(2, 4, 6-trimethylphenyl) imidazole and 2-bromopyridine, then reacting with silver oxide to prepare asilver-carbene intermediate complex, and finally reacting with iridium trichloride and potassium hexafluorophosphate to prepare the metal iridium-carbene complex. The complex is applied to an addition reaction of a terminal alkyne compound and an isatin derivative, a visible light source is additionally arranged, and the addition reaction can be well carried out at room temperature by weak organic base; the metal iridium-carbene complex disclosed by the invention is relatively high in efficiency when being used as a photocatalyst for the addition reaction, and the yield of an addition productis 82 wt% or above.

Description

technical field [0001] The invention relates to the technical field of synthesis and application of transition metal complexes, in particular to a metal iridium-carbene complex with photocatalytic performance and its preparation method and application. Background technique [0002] The N-heterocyclic carbene (NHC) structure has a high activity because the oxidation state of the carbene carbon atom is +2, and there are only 6 valence electrons around the carbene carbon atom, which does not reach the stable structure of the octet law. As a special reaction intermediate, cyclocarbene has very high reactivity and can form stable complexes with almost all metals. As a very strong electron donor, the carbene ligand can increase the electron density of the central metal, and the central metal can also have a certain feedback π bond to the carbene carbon atom, so that the carbene metal complex can exist stably and has high catalytic activity. . This enables the N-heterocyclic carb...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07F15/00B01J31/22C07D209/38
CPCB01J31/1815B01J35/004B01J2231/341B01J2531/827C07D209/38C07F15/0033
Inventor 吴泽颖孟佳瑶向梅张震威魏雪姣丁琳琳王玮
Owner CHANGZHOU INST OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap