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Chloroquinoxaline compound

A kind of fluoroquinoxaline, substituted quinoxaline technology, applied in the field of fluoroquinoxaline compounds, can solve the problems such as no reports on preparation method and application

Inactive Publication Date: 2012-12-19
XIAN MODERN CHEM RES INST
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  • Abstract
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Problems solved by technology

[0004] Therefore, fluorine atoms are introduced into the electron-deficient unit of quinoxaline to prepare a new type of electricity-deficient unit, and the material prepared by polymerization of bromine at both ends of the structure and the electricity-rich unit is expected to obtain similar performance in the field of polymer photovoltaic cells. , but so far there have been no reports on the preparation methods and applications of such materials

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Compound A

[0048] Follow the reaction equation shown in Scheme 2.

[0049]

[0050] Reaction equation of Scheme 2 compound A

[0051] (1) Preparation of 4-fluoro-3,6-dibromo-1,2-phenylenediamine (compound 1)

[0052] 5-Fluoro-4,7-dibromo-2,1,3-benzothiadiazole (5 g, 0.016 mol) was dissolved in 150 ml of absolute ethanol, and NaBH was added in batches at 0 °C 4 (11.1g, 0.29mol), and then reacted at room temperature for 20h. After the reaction, concentrate to remove ethanol, add 160ml of water, extract with ethyl acetate, wash the organic phase with saturated brine, and finally anhydrous MgSO 4 dry. The crude product obtained after concentrating and removing the organic solvent was subjected to silica gel column chromatography with n-hexane / ethyl acetate (25:1) as the eluent to obtain 4-fluoro-3,6-dibromo-1,2-phenylenediamine 3.5 g (compound 1), yield 78%.

[0053] (2) Preparation of 1,2-bis(3-octyloxyphenyl)ethanedione (compound 2)

[0054] Add LiB...

Embodiment 2

[0059] Example 2: Compound B

[0060] Follow the reaction equation as shown in Scheme 3.

[0061]

[0062] Reaction equation of Scheme 3 compound B

[0063] (1) Synthesis of 6-fluoro-5,8-dithiophene-2,3-bis(3-octyloxyphenyl)quinoxaline (compound 3)

[0064] Compound A (0.821g, 1.15mmol), 2-tributyltinthiophene (0.918g, 2.46mmol) and Pd(PPh 3 ) Cl 2 (32mg, 0.046mmol) dissolved in 20ml toluene, N 2 Reflux reaction under protection for 12 hours. The toluene was concentrated, and the crude product was recrystallized from n-hexane to obtain 0.66 g of 6-fluoro-5,8-dithiophene-2,3-bis(3-octyloxyphenyl)quinoxaline (compound 3) as an orange solid. The rate is 80%.

[0065] (2) Synthesis of 6-fluoro-5,8-bis(5-bromothiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline (compound B)

[0066] Compound 3 (0.5g, 0.7mmol) and NBS (0.261g, 1.47mmol) were dissolved in DMF (20ml), heated to 40°C, kept for 7h, cooled, filtered, and the filter cake was washed with methanol to obtain 6-fluoro -...

Embodiment 3

[0069] Example 3: Compound C

[0070] Follow the reaction equation as shown in Scheme 4.

[0071]

[0072] Reaction equation of Scheme 4 compound Ⅳ

[0073] Using compound A and 4-hexyl-2-tributyltinthiophene as raw materials, compound C was prepared according to the method for synthesizing compound B with a yield of 65%.

[0074] NMR characterization data: 1 HNMR (500MHz, CDCl 3 , ppm): δ=7.91 (d, 1H), 7.72 (s, 1H), 7.55 (dd, 2H), 7.50 (S, 1H), 7.20 (td, 2H), 7.09 (M, 2H), 6.97 ( dt, 2H), 4.05 (q, 4H), 2.64 (td, 4H), 1.80 (m, 4H), 1.66 (m, 4H), 1.49 (dd, 4H), 1.4-1.25 (m, 28H), 0.9 ( m,12H).

[0075] Electrochemical test: use CHI660D electrochemical workstation, use glassy carbon electrode as working electrode, platinum wire electrode as counter electrode, AgAg + The electrode is the reference electrode, Bu 4 N·PF 6 As an electrolyte, in a solvent of acetonitrile / o-dichlorobenzene=1:5, the HOMO energy of compound C determined by cyclic voltammetry is -5.58eV, which...

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Abstract

The invention belongs to the organic chemical field, and discloses a chloroquinoxaline compound, a structural general formula of the conjugated polymer is shown as I. The compound introduces a fluorine atom with a strong electrosorption characteristic on quinoxaline, thereby the HOMO energy level of the material can be effectively reduced, and the open-circuit voltage of a polymer photovoltaic cell can be enhanced. By using cyclic voltammetry determination of the HOMO energy of the compound, compared with a non-chloroquinoxaline derivative, the HOMO energy level of a single fluoropolymer is lower by 0.02-0.15eV than that of the non-chloroquinoxaline, and the HOMO energy level of the double fluoro polymer is lower by 0.05-0.3eV than that of the non-chloroquinoxaline. The compound can be taken as an intermediate of a polymer photovoltaic material for preparing the polymer photoactivity material with excellent performance. By using cyclic voltammetry determination of the HOMO energy of the compound A-I, compared with the non-chloroquinoxaline derivative, the HOMO energy level of the single fluoropolymer is lower by 0.02-0.15eV than that of the non-chloroquinoxaline, and the HOMO energy level of the double fluoro polymer is lower by 0.05-0.3eV than that of the non-chloroquinoxaline.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a fluoroquinoxaline compound. Background technique [0002] Quinoxaline and its derivatives have attracted much attention in the field of optoelectronics as a new type of charge-deficient unit due to the structure containing two nitrogen atoms with strong nucleophilic ability. The formation of donor-acceptor-donor (D-A-D) type polymers through coupling reactions and power-rich units has been applied in polymer solar cells. [0003] The highest occupied orbital (HOMO) energy level of the electron-deficient unit is the main factor affecting the open-circuit voltage of polymer solar cells. It has become a method to increase the open-circuit voltage by introducing fluorine atoms with electron-absorbing ability on the electron-deficient unit to reduce the HOMO energy. effective means. For example, in a class of PTB series materials reported by Luping Yu et al. in 2009, when PTB4 was...

Claims

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Application Information

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IPC IPC(8): C07D241/42C07D409/14H01L51/46
CPCY02E10/549
Inventor 高潮武海梅王维平丛志远田地安忠维刘建群
Owner XIAN MODERN CHEM RES INST
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