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

Iso-indigo derivative and applications of the iso-indigo derivative

A derivative, isoindigo technology, which is used in bis-indo-indocyanine indigo dyes, electrolytic capacitors, photovoltaic power generation, etc., can solve the problems of high price and complicated preparation process, and achieve low cost, easy preparation and cost reduction. Effect

Inactive Publication Date: 2011-09-14
EAST CHINA UNIV OF SCI & TECH
View PDF1 Cites 11 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The photosensitizing dye with the best photoelectric conversion efficiency so far is bipyridyl ruthenium complex (about 11.5%), because ruthenium is a rare metal, expensive, and its preparation process is more complicated

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
  • Iso-indigo derivative and applications of the iso-indigo derivative
  • Iso-indigo derivative and applications of the iso-indigo derivative
  • Iso-indigo derivative and applications of the iso-indigo derivative

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0036] The method for preparing target compound (compound shown in I formula) provided by the present invention, its main synthetic route is as follows:

[0037]

[0038] Among them: Ar 1 , Ar 2 , R 1 and R 2 has the same meaning as described above. The method comprises the steps of:

[0039] (1) In alkaline and catalyst [such as Pd 2 (dba) 3 etc.] and the presence of inert gas, compound A and (HO) 2 B-Ar 2 -CHO was placed in an aprotic polar solvent [such as tetrahydrofuran (THF), etc.], and kept at reflux for at least 10 hours, cooled, evaporated to remove the solvent, and the residue was dissolved in dichloromethane, washed with water, and the dichloromethane layer was washed with no dried over sodium sulfate, spin-dried, and subjected to silica gel column chromatography to obtain compound B;

[0040] (2) Also in alkaline and catalyst [such as Pd 2 (dba) 3 etc.] and the presence of inert gas, compound B and Ar 1 B(OH) 2 Repeat step (1) to obtain compound C; ...

Embodiment 1

[0059]

[0060] Add 533mg (2.36mmol) of compound 1, 500mg (2.36mmol) of compound 2, 15mL of glacial acetic acid and 0.1mL of concentrated hydrochloric acid into a 25mL two-neck round bottom flask, and heat to reflux for 24 hours. After cooling and suction filtration, the solid was washed with water, ethanol and ethyl acetate respectively, and vacuum-dried to obtain a brown solid (compound 3), with a yield of 90%.

[0061] 1 H NMR ((CD 3 ) 2 NCOD), δ: 10.7 (bs, 2H), 9.14 (d, J=8.7Hz, 2H), 7.22-7.15 (m, 4H). 1.35-1.15 (m, 6H), 0.86 (t, 3H). 13 C NMR (CDCl 3 ), δ: 170.3, 147.2, 134.0, 132.3, 127.0, 125.3, 122.6, 113.9.

[0062]

[0063] 420 mg (1 mmol) of compound 3 and 824 mg (6 mmol) of potassium carbonate were added to a 50 mL two-neck round bottom flask under argon protection, and 0.384 mL (2.2 mmol) of 1-bromooctane was injected with a syringe, and reacted at 100° C. for 18 hours. After cooling, it was poured into 200ml of water, stirred for 2 hours, and a gray-re...

Embodiment 2

[0077]

[0078] In a 50mL dry flask, add 322mg (0.5mmol) A-1, 15mg Pd 2 (dba) 3 , 10mg P(o-tyl) 3 and 0.5g of potassium phosphate, under the protection of argon, inject 12mL of tetrahydrofuran with a syringe. Heat to 70°C, inject 98mg (0.7mmol) of furanboronic acid aldehyde dissolved in 10mL tetrahydrofuran, raise the temperature to 85°C after the addition, and stir for 20h. Cool to room temperature, spin off the solvent, dissolve the residue with dichloromethane, wash with water, dry the dichloromethane layer with anhydrous sodium sulfate, spin dry, perform silica gel column chromatography, the developing solvent is petroleum ether / dichloromethane=2 / 1 To 1 / 1 (V / V), 168 mg of brown solid (compound B-2) was obtained, yield 51%.

[0079] 1 H NMR (CDCl 3 , 400MHz), δ: 9.70(s, 1H), 9.25(d, J=8Hz, 1H), 9.08(d, J=8Hz, 1H), 7.43(dd, J 1 =8Hz,J 2 =8Hz, 1H), 7.37(d, J=4Hz, 1H), 7.22(s, 1H), 7.18(dd, J 1 =12Hz,J 2 =8Hz, 1H), 6.98(d, J=4Hz, 1H), 6.93(s, 1H), 3.84(t, 2H), 3.74...

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 an iso-indigo derivative and applications of the iso-indigo derivative. The is formed by chemical modification on iso-indigo (matrix), i.e., one end is connected with different electron donating groups, while the other is connected with carboxyl groups which are electron withdrawing groups and used for being adsorbed on TiO2, therefore a series of electronic push-pull type compounds. As the matrix of the iso-indigo derivative serves as a conjugated system, the iso-indigo derivative has a good plane structure; as the iso-indigo derivative is connected with the electrondonating groups and the electron withdrawing groups, the electrons are easy to transfer in an excitated state, so that the iso-indigo derivative generate unique photoelectrochemical properties and can be used as a photosensitizer of dye sensitized solar cells.

Description

technical field [0001] The present invention relates to a derivative of isoindigo and its application. Background technique [0002] With the rapid development of human industrial civilization, mineral resources such as coal, oil and natural gas are increasingly depleted, and the resulting energy crisis and environmental pollution have become serious problems that need to be solved urgently. Therefore, people urgently need to find other new alternative energy sources. Dye-sensitized solar cells (B.O'Regan, M. Nature, 1991, 353, 737-740), because of its low cost, it has potential practical value. [0003] Dye-sensitized solar cells (DSSCs) are usually composed of semiconductor oxide nanoporous membranes, dye sensitizers, redox electrolytes, and Pt electrodes, among which dye sensitizers with broad spectrum, high molar extinction coefficient, and low cost are the key components of the entire DSSC. core part of the system. So far, the photosensitive dye with the best photo...

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): C09B7/02C09B67/28C07D403/04C07D409/14C07D405/14C09K11/06H01G9/042H01G9/20H01L51/42H01L51/46
CPCY02E10/50Y02E10/542Y02E10/549
Inventor 花建丽应伟江王兵郭福领武文俊曲大辉田禾
Owner EAST CHINA UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com