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Linear acene compound based on triptycene and synthesis and application thereof

A compound, the technology of triptycene, applied in the field of linear acene compounds and their synthesis and application, can solve the lack of trimer molecular design, performance research and application, and research on the synthesis and application of acene trimer compounds Issues not reported

Active Publication Date: 2021-02-02
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the design, performance research and application of trimer molecules are very lacking.
[0005]There is no report on the synthesis and application of acene-based trimer compounds with tripletene as the core core extending vertically

Method used

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  • Linear acene compound based on triptycene and synthesis and application thereof
  • Linear acene compound based on triptycene and synthesis and application thereof
  • Linear acene compound based on triptycene and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] This embodiment synthesizes compound 2-1 and 3-1-1

[0078] Synthesis of compound 1-1

[0079] Under the condition of nitrogen protection, triptycene (1.0g, 3.9mmol), phthalic anhydride (3.7g, 24.9mmol) and 50mL tetrachloroethylene were added to a 100mL three-necked flask, and after stirring evenly, the trichloro Aluminum chloride (6.5 g, 48.7 mmol) was added slowly. Heated to reflux at 115°C for 16h. After the reaction was complete, it was cooled to room temperature, poured into 5% hydrochloric acid in ice water, and stirred for 30 min. The solid was filtered, washed with water, and dried in vacuo. The obtained crude product was dissolved in 100 mL of acetonitrile, filtered, and the filtrate was spin-dried to obtain triptylenonic acid derivative 1-1 (2.3 g), with a yield of 84%. Triptylenonic acid derivative 1-1 is a mixture of two stereoisomers, which is directly used in the next reaction.

[0080]

[0081] Synthesis of Compound 2-1

[0082] Compound 1-1 (1g,...

Embodiment 2

[0085] This embodiment synthesizes compound 3-1-1

[0086] Synthesis of compound 3-1-1

[0087] Under the condition of nitrogen protection, triisopropylsilylacetylene (4.2mL, 18.7mmol) was dissolved in 10mL ether, cooled to 0°C, and then 3.3mL n-butyllithium (2.5M) was slowly dissolved in 30min Drop into the mixture and stir at 0°C for 1h. Then, a mixed suspension of compound 2-1 (0.5 g, 0.78 mmol) in tetrahydrofuran (10 mL) was added in one portion, and then the mixture was raised to room temperature and stirred for 12 h. After the reaction was complete, 10 mL of a saturated stannous chloride solution of 10% hydrochloric acid was added dropwise to the reaction solution, and stirring was continued for 1 h. The liquid was separated, and the upper organic phase was dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation. Using pure petroleum ether as the developer for column chromatography separation, the light yellow product 3-1-1 (319 mg) was ...

Embodiment 3

[0090] This embodiment synthesizes compound 3-1-3

[0091] Synthesis of compound 3-1-3

[0092] Under nitrogen protection, 2,6-diisopropylbromobenzene (4.5g, 18.7mmol) was dissolved in 10mL of ether, cooled to 0°C, and then 3.3mL of n-butyllithium (2.5 M) slowly drop into the mixture, and stir at 0°C for 1 h. Then, a mixed suspension of compound 2-1 (0.5 g, 0.78 mmol) in tetrahydrofuran (10 mL) was added in one portion, and then the mixture was raised to room temperature and stirred for 12 h. After the reaction was complete, 10 mL of a saturated stannous chloride solution of 10% hydrochloric acid was added dropwise to the reaction liquid, and stirring was continued for 1 h. The liquid was separated, and the upper organic phase was dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation. Using pure petroleum ether as the developer for column chromatography separation, the light yellow product 3-1-3 was obtained.

[0093]

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Abstract

The invention discloses a linear acene compound based on triptycene and synthesis and application thereof. The structural formula of the compound is shown as T-X, wherein in the structural formula, the substituted position is 2-position or 3-position; if yes, the benzene ring is of a benzoquinone structure; i is a natural number of 0-5; R is a substituted or non-substituted silyl ethynyl group, asubstituted or non-substituted alkyl ethynyl group, a substituted or non-substituted alkoxy ethynyl group, a substituted or non-substituted aryl ethynyl group, a substituted or non-substituted heterocyclic aryl ethynyl group, a substituted or non-substituted heterocyclic ethynyl group, a substituted or non-substituted silane group, a substituted or non-substituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic aryl group, a substituted or unsubstituted heterocyclic group or a hydrogen atom; and when R is a hydrogen atom, i is not 0. According to the invention, the triptycene is used as a parent nucleus for the first time to design and synthesize the trimer of the linear acene compound, and theapplication of the triptycene in organic photoelectric devices is researched.

Description

technical field [0001] The invention relates to the technical field of organic materials, in particular to a triptycene-based linear acene compound and its synthesis and application. Background technique [0002] Three-dimensional materials with C3 symmetry have attracted much attention recently because of their significance in sensors, photoelectric conversion, energy storage, and supramolecular self-assembly. A notable feature of this type of material is that the molecular structure contains three structural units that are 120° to each other, so this type of molecule generally has a large intramolecular free volume (intramolecular free volume), which is ideal for preparing molecular cages and two-dimensional polymers. (2D polymers) important structural unit. Among them, tripterene is one of the most common three-dimensional material building blocks. It is an aromatic hydrocarbon synthesized by Diels–Alder reaction of anthracene and benzyne. In the three-dimensional mole...

Claims

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Application Information

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IPC IPC(8): C07C50/22C07F7/08C07C15/20C07C43/166C07C15/56C07D333/08C07D213/16C07C51/09C07C65/34C07C46/00C09K11/06H01L51/50H01L51/54
CPCC07C50/22C07F7/0805C07C15/20C07C43/166C07C15/56C07D333/08C07D213/16C07C51/09C07C65/34C07C46/00C09K11/06C09K2211/1011C09K2211/1029C09K2211/1092C07C2603/90H10K85/624H10K85/654H10K85/655H10K85/40H10K50/00H10K50/11H10K2101/10Y02E10/549
Inventor 张磊张国伟
Owner BEIJING UNIV OF CHEM TECH
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