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Star molecule of truxene-perylene-series derivative and preparation method thereof

A technology of trisindene and its derivatives, which is applied in the fields of organic and fine chemicals, can solve problems such as the scarcity of star-shaped N-type organic semiconductors, and achieve the effects of improving solubility, thermal stability, and film formation

Inactive Publication Date: 2012-01-18
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, the current conjugated molecules of peryleneimides are basically limited to linear conjugated organic molecules, and star-shaped conjugated molecules are still blank, and star-shaped N-type organic semiconductors are even scarcer. Star-shaped molecules with perylene derivatives as conjugated branched chains can fill this gap

Method used

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  • Star molecule of truxene-perylene-series derivative and preparation method thereof
  • Star molecule of truxene-perylene-series derivative and preparation method thereof
  • Star molecule of truxene-perylene-series derivative and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0028] The preparation of embodiment 1 intermediate 1

[0029]

[0030] In a 50mL flask, add 400mg of tripolyindene borate (compound Tr), 610mg of N,N'-bis(3-pentyl)-1-bromo-3,4,9,10 perylene imide, and Potassium 800mg, Pd(PPh 3 ) 2 Cl 2 40mg, chloroform 25mL, under argon atmosphere, heated to reflux for 6h. After the reaction was completed, 475 mg of a red solid was obtained through column chromatography separation, with a yield of 60%. 1 H-NMR (400MCDCl 3 ): δ=8.69(m, 18H), 8.19-8.06(m, 6H), 7.66(s, 3H), 7.54(s, 3H), 5.30(m, 6H), 3.03(m, 6H), 2.30- 1.57(m, 30H), 1.06-0.57(m, 96H).

Embodiment 2

[0031] The preparation of embodiment 2 compound 2

[0032]

[0033] In a 250mL flask, add compound 1 475mg, 100mL tetrahydrofuran, solar simulator (AM1.5, 100mW / cm 2 ) irradiation, add elemental iodine 5mg, react at room temperature for 6h. Tetrahydrofuran was distilled off under reduced pressure, and 426 mg of compound 2 was obtained by column chromatography, with a yield of 90%. 1 H-NMR (400M CDCl 3 ): δ=10.62(d, 9H), 9.67(s, 3H), 9.35(d, 6H), 9.12(d, 6H), 5.38(m, 6H), 3.82(m, 6H), 3.15(m, 6H), 2.54(m, 12H), 2.18(m, 12H), 1.18-0.72(m, 84H), 0.37(m, 18H).

Embodiment 3

[0034] The preparation of embodiment 3 compound 3

[0035]

[0036] In a 50mL flask, add tripolyindene borate (compound Tr) 400mg, 1-bromoperylenetetracarboxylate 832mg, potassium hydroxide 820mg, Pd (PPh 3 ) 2 Cl 2 40mg, chloroform 25mL, under argon atmosphere, heated to reflux for 6h. After the reaction was completed, 3540 mg of the compound was obtained through column chromatography separation, with a yield of 60%. 1 H-NMR (400M CDCl 3 ): δ=8.46(s, 3H), 8.35(m, 6H), 8.21(s, 3H), 8.15(m, 6H), 7.96(s, 3H), 7.58(m, 3H), 7.48(m, 6H ), 4.38-4.23(m, 24H), 2.98(s, 6H), 2.01-1.79(m, 30H), 1.69-1.39(m, 24H), 1.26-0.93(m, 72H), 0.66(m, 30H ).

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Abstract

The invention discloses a star molecule of truxene-perylene-series derivative and a preparation method thereof, belonging to the fields of organic chemical industry and fine chemistry industry. The star molecule mainly comprises truxene-perylene imide, truxene-perylene tetraformic ether and truxene-perylene anhydride. The preparation method comprises the following steps of: undergoing a coupling reaction on 2,7,12-triboric acid ester-5,5,10,10,15,15-hexaalkyl-truxene serving as a raw material and 1-bromine-3,4,9,10 perylene imide to obtain a coupling product of truxene and perylene imide, and undergoing a closed ring reaction under illumination to obtain a star molecule of the truxene-perylene imide; undergoing a coupling reaction on 2,7,12-triboric acid ester-5,5,10,10,15,15-hexaalkyl-truxene serving as a raw material and 1-bromine-3,4,9,10 perylene tetraformic ether to obtain a coupling product of truxene and perylene tetraformic ether, and undergoing a closed ring reaction under illumination to obtain a star molecule of the truxene-perylene tetraformic ether; hydrolyzing the truxene-perylene tetraformic ether to obtain truxene-perylene anhydride; and reacting the truxene-perylene anhydride with organic amine to generate truxene-perylene imide. By adopting the series of compounds, the conjugated systems of perylene imide and the like are expanded remarkably, and a novel material is provided for the research of organic semiconductors.

Description

technical field [0001] The present invention relates to a class of star-shaped molecules of tripolyindenoperylene derivatives and a preparation method thereof. The series of star-shaped molecules include: tripolyindenoperyleneimide, tripolyindenoperylene tetracarboxylate, Trimeric indenoperylene anhydride. It belongs to the field of organic chemical industry and fine chemical industry. Background technique [0002] Organic semiconductors, also known as organic charge transport materials, usually refer to conjugated materials composed of organic molecules with a conjugated structure whose conductivity is between conductors and insulators. Compared with inorganic semiconductors, organic semiconductors have the following advantages: [0003] (1) Organic semiconductors can be prepared in large quantities through chemical reactions at low cost. [0004] (2) There are many types of organic molecules, and the chemical structure is easy to change, which is beneficial to the desig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22C07D493/22C07C69/76C07C67/333
Inventor 肖义谢元朋
Owner DALIAN UNIV OF TECH
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