Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of indoline compound and its application

A compound, indoline technology, applied in the field of dye compounds, can solve problems such as limited application, narrow light capture range, and poor planarity of compounds

Active Publication Date: 2020-05-26
HEBEI NORMAL UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still two important defects in the existing indoline compounds: 1) the light-harvesting range of the compound is still narrow; 2) the compound is poor in planarity, resulting in weak self-assembly ability, making it suitable as a hole transport material or Lower mobility / conductivity for electron transport materials
These two problems directly affect the performance of organic molecules based on indoline compounds in the above devices, limiting their application in the above devices

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 indoline compound and its application
  • A kind of indoline compound and its application
  • A kind of indoline compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1 is synthesized (R 1 =R 2 =CH 3 )

[0026]

[0027] Add 5.00g (23.26mmol) of compound 1 and 6.64g (28.99mmol) of compound 2 into a 250mL single-necked flask, add 150mL of methanol, install a water trap and stir at reflux at 70° for 24 hours to stop the reaction. After the solvent was spin-dried, the reactant was washed with water several times, extracted with ethyl acetate, and the ethyl acetate layer was spin-dried and purified by column chromatography to obtain 5.5 g of oily compound 2. 1 HNMR (500Hz, CDCl 3 ): 7.61(s,1H),7.54(d,J=8.0Hz,1H),7.15(d,J=8.0Hz,1H),3.94(s,3H),2.35(s,3H).

[0028]

[0029] Add 2.29g (1.00mmol) compound 2 and 1.57g (1.00mmol) compound 3, Cu powder 0.64g (1.00mmol), 1.9gCuI (1.00mmol), K 2 CO 3 Solid 2.07g (1.5mmol), 50mL o-dichlorobenzene, heated to 180° under nitrogen protection, refluxed and stirred for 24-48 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. use CH 2 Cl...

Embodiment 2

[0036] Embodiment 2 is synthesized (R 1 =CH 3 , R 2 =C 8 h 17 )

[0037]

[0038] Add 1.00 g of compound 5 into a single-necked round bottom flask, take 10 mL of n-octylmagnesium bromide, stir and reflux for 12 h under deoxygenation and nitrogen protection, wash the reaction solution with saturated ammonium chloride solution and extract with ethyl acetate, spin dry and pass through the column Purification yielded 0.60 g of compound 8. 1 H NMR (500Hz, CDCl 3 ): 7.89(s, 1H), 7.18(d, J=7.5Hz, 1H), 7.12(d, J=8.5Hz, 1H), 6.99-7.02(m, 2H), 6.88(t, J=7.5Hz ,1H),6.24(d,J=8.5Hz,1H),4.53(t,J=8.5Hz,1H),3.98(t,J=8.5Hz,1H),2.40(s,3H),2.06-2.08 (m,1H),1.80-1.85(m,5H),1.46-1.52(m,10H),1.31-1.38(m,18H),0.90(t,J=8.5Hz,6H).

[0039]

[0040] Add 0.11g of compound 8 to a 25mL single-necked bottle, add 0.4g of cation exchange resin Amberlyst 15, add 15mL of toluene and install a water separator device, stir and reflux for 12h, the reactant is suction filtered, the filtrate is spin-d...

Embodiment 3

[0041] Embodiment 3 applies compound 7 to synthetic sensitizing dyes

[0042]

[0043] Add 0.51g of compound 7 to a 100mL single-necked bottle, and use CH 2 Cl 2 Dissolve, add 0.41g N-bromosuccinimide solution dissolved in acetonitrile to a constant pressure dropping funnel under ice bath, react in the dark for 3 hours, wash the reaction solution with water, extract with ethyl acetate, spin dry, and purify by column to obtain 0.43g of compound 10 , yield 66.48%. 1 H NMR (500Hz, Acetone-d6): 7.25-7.28 (m, 2H), 7.12 (s, 1H), 6.99 (d, J=8.0Hz, 1H), 6.70 (d, J=8.0Hz, 1H), 4.70(t, J=8.5Hz, 1H), 3.98(t, J=8.5Hz, 1H), 2.29(s, 3H), 2.05-2.14(m, 2H), 1.98-2.01(m, 2H), 1.82 -1.87(m,2H),1.70(s,3H),1.43(s,3H).

[0044]

[0045] Dissolve 0.2g (0.54mmol) of compound 10 in dry THF into a 50mL three-neck flask, stir the reaction substrate under nitrogen protection until the temperature drops to -78°, slowly add 2mL of n-BuLi dropwise and stir for 1-2h, Slowly add 0.51g (2.71mmol) t...

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 an indoline compound. The compound has a structure shown in formula (I): in formula (I): R 1 for C 1 ~C 12 Hydrocarbyl or C 1 ~C 12 Alkoxy or C 4 ~C 20 Heterocyclyl, wherein the heteroatom of said heterocyclyl is N, S or O; R 2 for C 1 ~C 12 Hydrocarbyl. The compound mentioned in the invention can be used as an intermediate for synthesizing various sensitizing dyes, hole-transporting materials and electron-transporting materials.

Description

technical field [0001] The invention relates to a dye compound and its use, in particular to an indoline compound and its use. 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. Organic thin-film solar cells, such as dye-sensitized solar cells, perovskite solar cells, and organic polymer cells, have potential practical value due to their low cost. In the above-mentioned photovoltaic devices, organic molecules, as sensitizing dyes, hole transport materials, and electron transport materials, greatly affect the performance of the devices. [0003] Indoline compounds are widely used in the above materials due to their good fluorescence properties and suitable ener...

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): C07D471/06C07D519/00C09K11/06H01G9/20H01L51/50H01L51/54
CPCH01G9/2059C09K11/06C07D471/06C07D519/00C09K2211/1081C09K2211/1059C09K2211/1029C09K2211/1007H10K85/655H10K85/6572H10K50/15H10K50/16Y02E10/542
Inventor 刘博王亚军张凤玉张晓敏
Owner HEBEI NORMAL UNIV