Star-shaped triaryl borane compounds as well as preparation method and application thereof

A technology of star-shaped triarylborane and compound, applied in the field of fluorescent probes, can solve the problems of low reaction sensitivity, poor selectivity, long reaction time and the like

Active Publication Date: 2013-12-25
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Usually the first two types of fluorescent probes have the disadvantage of poor selectivity that is difficult to overcome, and it is difficult to become a fluorescent probe for highly selective recognition of fluoride ions
The recognition of the third type of fluorescent probe is to change the fluorescence of the system through the reaction bet

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
  • Star-shaped triaryl borane compounds as well as preparation method and application thereof
  • Star-shaped triaryl borane compounds as well as preparation method and application thereof
  • Star-shaped triaryl borane compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Preparation of 1,2-bis(4-(bis(2,4,6-trimethylphenyl)boryl)phenyl)acetylene (B-B)

[0067]

[0068] Add 500mg (1.487mmol) of bis(4-bromophenyl)acetylene and 10mL of freshly distilled tetrahydrofuran into a 25mL Schlenk bottle. After removing water and oxygen, place the system in a low-temperature bath at -78°C, and add 1.8mL of 2. 2M (3.96mmol) n-BuLi solution. Keep at -78°C, stir the reaction for 2 hours, and add 4 mL of 808 mg (3.01 mmol) bis(2,4,6-trimethylphenyl) boron fluoride-tetrahydrofuran (THF) solution dropwise. After the dropwise addition, the reaction system naturally rose to room temperature and reacted at room temperature for 24 hours. The reaction was quenched by adding water, THF was removed by rotary evaporation, and the aqueous phase was extracted three times with dichloromethane, and the organic phases were combined and washed three times with saturated brine and water respectively. The organic phase was dried with anhydrous sodium sulfate, spin-d...

Embodiment 2

[0070] Preparation of bis(4-(9-carbazole)phenyl)acetylene and 1-(4-bromophenyl)-2-(4-(9-carbazole)phenyl)acetylene

[0071]

[0072] Add 102.6mg (0.305mmol) bis(4-bromophenyl) acetylene, 130.3mg (0.799mmol) carbazole, 170mg (1.232mmol) anhydrous potassium carbonate, 38mg (0.594mmol) activated copper powder in a 50mL two-necked flask , 52mg (0.197mmol) of 18-crown-6 and 8mL of o-dichlorobenzene were passed through nitrogen for 15min, heated to 180°C under nitrogen atmosphere, and refluxed for 24h. The reaction system was cooled to room temperature, filtered under reduced pressure, and the filtrate was spin-dried, and separated by using petroleum ether / dichloromethane as an eluent chromatographic column (200-300 mesh silica gel) to obtain a white solid, bis(4-(9- Carbazole)phenyl)acetylene 45mg, yield 30%; 1-(4-bromophenyl)-2-(4-(9-carbazole)phenyl)acetylene 60mg, yield 46.6%. Increase the proportion of carbazole (>6eq), mainly to obtain bis(4-(9-carbazole)phenyl)acetylene; ...

Embodiment 3

[0076] Preparation of 1-(4-(bis(2,4,6-trimethylphenyl)boryl)phenyl)-2-(4-(9-carbazole)phenyl)acetylene (B-C)

[0077]

[0078] Add 155 mg (0.368 mmol) 1-(4-bromophenyl)-2-(4-(9-carbazole) phenyl) acetylene and 30 mL freshly distilled tetrahydrofuran into a 50 mL schlenk bottle, repeat vacuum pumping-nitrogen three times, and In a low-temperature bath at -78°C, 0.3mL of 2.2M (0.7mmol) n-butyllithium solution was added dropwise under a nitrogen atmosphere. Keep the low-temperature bath at -78°C, stir the reaction for 2 hours, and add 2 mL of 148 mg (0.558 mmol) bis(2,4,6-trimethylphenyl) boron fluoride-tetrahydrofuran solution dropwise. After the dropwise addition, the reaction system was allowed to rise to room temperature naturally, and reacted at room temperature for 24 h. The reaction was quenched by adding water, THF was removed by rotary evaporation, the aqueous phase was extracted three times with dichloromethane, the organic phases were combined, and washed three tim...

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 discloses star-shaped triaryl borane compounds. In the invention, star-shaped triaryl borane compounds with a rigid skeleton are synthesized through molecular design; and the invention also discloses a preparation method of the star-shaped triaryl borane compounds. In the compounds, the steric hindrance of the aryl substituent on the boron atom is great, thus effectively blocking the binding of the boron atom with other anions, so that the compounds have the advantages of specificity, high sensitivity and rapid response to fluoride ion detection; the compounds have a structural general formula as shown in the specification, wherein X is a positive integer, Y is zero or a positive integer and X + Y = 6; the compounds provided by the invention can carry out characteristic reaction with fluoride ions so as to specifically, rapidly and quantitatively detect fluoride ions with high sensitivity.

Description

technical field [0001] The invention belongs to the field of fluorescent probes, in particular to star-shaped triarylborane compounds and their preparation methods and applications. Background technique [0002] Anions in organisms play an important role in many aspects such as signal transduction and maintaining charge balance. Therefore, fluorescent probes that recognize anions are of great significance in biological research. Fluoride ions play an important role in ensuring human health, but once the fluoride ion content exceeds the range required by a healthy human body (1ppm), it will damage the health of the body and even cause fluorosis bone cancer. Therefore, fluoride ion recognition has always been a research hotspot. [0003] Fluorescent probes have the characteristics of easy detection, high sensitivity, and convenient use. Therefore, finding fluorescent probes with high selectivity for recognizing fluoride ions has always been the direction of chemists' efforts....

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): C07F5/02C09K11/06G01N21/64
Inventor 曾毅唐海云李嫕陈金平李迎迎
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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