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Preparation method of truxene-based star-like compound

A technology of a compound, dibromoindanal, which is applied in the field of preparation of star compounds, can solve the problems of complex reaction, many synthesis steps, and low yield, and achieve good reaction selectivity, simple synthesis route, and mild reaction conditions Effect

Active Publication Date: 2017-08-18
江苏盛叶欣化工新材料有限公司
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  • Abstract
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Problems solved by technology

However, star compounds with a donor-acceptor structure still have shortcomings such as many synthetic steps, complex reactions, and low yields. Therefore, it is important to design and synthesize novel star compounds that are easy to synthesize with good energy / electron transfer processes. the meaning of

Method used

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  • Preparation method of truxene-based star-like compound
  • Preparation method of truxene-based star-like compound
  • Preparation method of truxene-based star-like compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Dissolve 2,7-dibromotriindaldehyde (0.7mmol, 605.49mg), BODIPY borate derivative (0.7mmol, 315.10mg), anhydrous sodium carbonate (12.64mmol, 1.34g) under argon atmosphere in tetrahydrofuran (60 mL), and a mixture of methanol and water (CH 3 OH / H 2 O=5mL / 5mL), add catalyst Pd (PPh 3 ) 4 (0.07mmol, 77.39mg), heated to reflux for 24 hours. After the reaction, the organic matter was extracted with dichloromethane and washed with saturated ammonium chloride solution. The organic layers were combined and dried over anhydrous sodium sulfate. Analysis, separation and purification yielded 233.25 mg of product TB (yield 30.07%). UV-vis (CH 2 Cl 2 ), λ max / nm[ε×10 -5 / (L·mol -1 cm -1 )]: 318 (0.192), 502 (0.219) (with figure 1 ); 1 H NMR (CDCl 3 , 600MHz, ppm) δ 10.15(s, 2H), 8.44-8.48(m, 1H), 8.25-8.28(m, 1H), 7.92-7.96(m, 3H), 7.44(d, J=6Hz, 2H) , 7.61(s, 1H), 6.02(s, 2H), 2.92-3.03(m, 6H), 2.09-2.24(m, 6H), 1.54(d, J=12Hz, 6H), 0.44-0.52(m, 26H).Emission Wavele...

Embodiment 2

[0032] Compound TB (0.15mmol, 166.22mg) and porphyrin derivative (0.15mmol, 144.36mg) were dissolved in dry tetrahydrofuran (40mL) under argon atmosphere, anhydrous sodium carbonate (2.7mmol, 286.17mg) was added, And add catalyst Pd(PPh 3 ) 4 (0.015mmol, 17.33mg), then add methanol and water mixture (CH 3 OH / H 2 O=1mL / 1 mL), the reaction system was reacted under reflux conditions for 24 hours. After the reaction, the organic matter was extracted with dichloromethane and washed with saturated ammonium chloride solution. After the organic layers were combined, they were dried over anhydrous sodium sulfate and reduced pressure The solvent was distilled off, and the product TBP was separated and purified by silica gel column chromatography with dichloromethane-petroleum ether as the eluent to obtain 73.5 mg (yield: 26.4%). UV-vis (CH 2 Cl 2 ), λ max / nm[ε×10 -5 / (L·mol -1 cm -1 )]: 329 (0.97319), 424 (6.55283), 502 (1.07515), 551 (0.26879), 593 (0.10195) (with figure 2 ...

Embodiment 3

[0034] The compound TBP (0.0217mmol, 40mg), fullerene (0.109mmol, 78.20mg) and sarcosine (0.217mmol, 19.33mg) were dissolved in dry toluene (30mL), and heated under reflux under argon for 12 hours After the reaction is over, the solvent is distilled off under reduced pressure and is separated and purified by silica gel column chromatography with dichloromethane-petroleum ether as an eluent to obtain the product TBP-C 60 It was 34.72 mg (61.51% yield). UV-vis (CH 2 Cl 2 ), λ max / nm[ε×10 -5 / (L·mol -1 cm -1 )]: 257 (1.32673), 316 (0.78043), 424 (3.56396), 502 (0.57231), 549 (0.14308), 590 (0.039020) (attached image 3 ); 1 H NMR (CDCl 3 , 600MHz, ppm) δ9.04-9.06(m, 4H), 9.00(t, J=3.0Hz, 2H), 8.96(s, 2H), 8.71-8.73(m, 1H), 8.53(t, J= 3.6Hz, 2H), 8.42-8.46(m, 1H), 8.29(s, 2H), 8.23(s, 2H), 8.09-8.14(m, 5H), 7.95(t, J=6.6Hz, 2H), 7.85(s, 1H), 7.74-7.80(m, 7H), 7.42-7.44(d, J=7.2Hz, 2H), 6.02(s, 2H), 5.05(s, 1H), 4.94-4.96(m, 1H), 4.21-4.22(m, 1H), 3.28-3.31(m, 2H), 3.04...

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Abstract

The invention discloses a structure and a preparation method of a truxene-based star-like compound (TBP-C60). The preparation method is implemented by the following steps: by taking 7,12-dibromo-truxene-aldehyde derivative as a raw material and taking tetrahydrofuran as a solvent, performing Suzuki reaction on the raw material, the solvent and a BODIPY borate derivative under the catalysis action of tetra(triphenylphosphine) palladium, thus obtaining a truxene-BODIPY binary system compound TB; then by taking the TB and a porphyrin borate derivative as raw materials, performing reaction under the catalysis action of the tetra(triphenylphosphine) palladium, thus obtaining a BODIPY-truxene-porphyrin ternary system compound TBP; then performing cycloaddition reaction on the TBP, sarcosine and fullerene through 1,3-dipole, thus obtaining the star-like compound TBP-C60 in which the truxene is used as a core and the porphyrin, the BODIPY and the fullerene are used as arms. The preparation method of the star-like compound is simple, mild in reaction condition and easy and convenient to operate, shows excellent energy transfer efficiency and high heat stability and can be used for a light absorption antenna, a solar panel, light-simulated biological photosynthesis and other aspects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of a star compound based on trisindene. Background technique [0002] Light-induced energy / electron transfer plays an important role in photochemical reactions, solar energy utilization, and photosynthetic mechanisms. The application of molecular models based on light-induced energy / electron transfer mechanisms in optical molecular devices, solar cells, and artificial photosynthesis has become a very active research field at home and abroad. Dye molecules with electron / energy donating and acceptor properties have shown broad application prospects in organic optoelectronic functional materials. In molecular models of different structural types, the unique three-dimensional star-like structure of star compounds is conducive to the regulation of the photoelectric properties and morphological characteristics of molecules, and multiple outwardly extending...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/022
Inventor 徐海军袁雪梅杜欣陶家宇姚烁
Owner 江苏盛叶欣化工新材料有限公司
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