Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of preparation method of 10h-spiro[acridine-9,9`-fluorene] and its derivatives

A derivative, acridine technology, applied in the field of preparation of 10H-spiro[acridine-9,9'-fluorene] and its derivatives, can solve problems such as hindering the application of such compounds, complicated synthesis methods, etc., and achieves a suitable The effect of large-scale production, high yield and purity, and safe preparation process

Inactive Publication Date: 2020-05-29
SHIHEZI UNIVERSITY
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing synthetic methods are cumbersome, and dangerous reagents or transition metals are usually used in the preparation, which hinders the application of such compounds in optoelectronic materials

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
  • A kind of preparation method of 10h-spiro[acridine-9,9`-fluorene] and its derivatives
  • A kind of preparation method of 10h-spiro[acridine-9,9`-fluorene] and its derivatives
  • A kind of preparation method of 10h-spiro[acridine-9,9`-fluorene] and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0035] The invention provides a preparation method of 10H-spiro[acridine-9,9'-fluorene] and derivatives thereof, which is characterized in that, comprising the following steps:

[0036] Under protective atmosphere conditions, the imine compound, potassium fluoride, 18-crown-6 and phenyl mesylate compound are mixed for cycloaddition reaction to obtain 10H-spiro[acridine-9,9' - fluorene] and derivatives thereof;

[0037] Wherein, the imine compound has a structure shown in formula I:

[0038]

[0039] In formula I, R 1 Including hydrogen, methyl, methoxy or chlorine; R 3 including hydrogen or bromine;

[0040] The phenyl mesylate compound has the structure shown in formula II:

[0041]

[0042] In formula II, R 2 , R 2 ' and R 2 " independently includes hydrogen, methyl, methoxy, chloro or fluoro.

[0043] In the present invention, under protective atmosphere conditions, imine compounds, potassium fluoride, 18-crown-6 and phenyl mesylate compounds are mixed for cyc...

Embodiment 1

[0066] (1) At room temperature, add 25 mL of chloroform to a mixture of 5.0 mmol fluorenone and 8.5 mmol aluminum trichloride, add a mixed solution of 8.0 mmol aniline and 25.5 mmol triethylamine under stirring conditions, stir for 3.5 hours, add 4 mol / L of sodium hydroxide solution was quenched, the organic phase was extracted with dichloromethane, separated and purified by alumina column chromatography to obtain N-phenyl-9H-fluorene-9-imine (see Yan Liu et al. "Facile Synthesis of Triarylmethanimine Promoted by a Lewis Acid-Base Pair: Theoretical and Experimental Studies", Aust. J. Chem. 2012, 65, 1390-1395).

[0067] The reaction equation is:

[0068]

[0069] (2) Put the 25mL reaction tube into an infrared drying oven to dry for 30min, after cooling to room temperature, accurately weigh 0.1mmol of N-phenyl-9H-fluorene-9-imine obtained in step (1), and 0.45mmol of fluorine-9-imine Potassium and 0.45mmol 18-crown-6 were placed in the reaction tube, the system was evacua...

Embodiment 2

[0078] (1) N-(p-tolyl)-9H-fluoren-9-yl imine is prepared according to the method of Example 1, the difference is only that aniline is replaced by p-methylaniline;

[0079] The reaction equation is:

[0080]

[0081] (2) According to the scheme of Example 1, 24.8 mg of 2-methyl-10H-spiro[acridine-9,9'-fluorene] was prepared, the only difference being that N-phenyl-9H-fluorene-9-imine Replaced with N-(p-tolyl)-9H-fluoren-9-yl imine;

[0082] The reaction equation is:

[0083]

[0084] The obtained 2-methyl-10H-spiro[acridine-9,9'-fluorene] was a white solid with a yield of 72%, a purity of more than 99%, and a melting point of 225.2-227.1°C.

[0085] The analysis results are as follows:

[0086] 1 HNMR (400MHz, DMSO-d 6 )δ9.12(s, 1H), 7.92(d, J=7.5Hz, 2H), 7.37(td, J=7.4, 1.2Hz, 2H), 7.26–7.16(m, 4H), 7.05–6.99(m , 1H), 6.96–6.92(m, 1H), 6.88(d, J=2.5Hz, 2H), 6.45(ddd, J=8.3, 7.1, 1.4Hz, 1H), 6.08(dd, J=7.8, 1.4 Hz, 1H), 5.93(d, J=1.7Hz, 1H), 1.90(s, 3H);

[0087] ...

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

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention provides a preparation method of 10H-spiro[acridine-9,9'-fluorene] and a derivative thereof, and belongs to the technical field of organic synthesis. According to the invention, an iminecompound, potassium fluoride, 18-corona-6 and methanesulfonic acid ester compound are taken as raw materials to perform cycloaddition reaction, in the whole reaction, a 'one-pot method' is utilized to complete synthesis of 10H-spiro[acridine-9,9'-fluorene] and the derivative thereof with only one step; and compared with conventional methods, according to the invention, dangerous reagent or transition metal catalysis does not need to be used in the preparation process, and the preparation process is more safe and environment-friendly, and 10H-spiro[acridine-9,9'-fluorene] and the derivative thereof have relatively high yield and purity; in addition, the preparation method provided by the invention is low in production cost, simple in operation and suitable for large-scale production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 10H-spiro[acridine-9,9'-fluorene] and derivatives thereof. Background technique [0002] Traditional fluorescent red, green, and blue emitters cannot meet the requirements of high-efficiency, high-brightness, high-contrast, and long-life bright full-color displays. Therefore, organic triplet red, green, and blue light-emitting materials (phosphorescent materials) Research has been one of the important developments. In triplet blue light-emitting materials, arylamino-containing organic compounds are usually used as host materials, such as 4,4-N,N-dicarbazole-biphenyl (CBP), but this compound does not have enough triplet energy to perform efficient energy transfer. [0003] The inherent non-conjugated orthorhombic configuration of molecules with a spiro core makes it a potential for constructing highly photosensitive triplet and thermodynamically...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/20
CPCC07D221/20
Inventor 何林王伟华杜广芬顾承志
Owner SHIHEZI UNIVERSITY
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com