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Dinaphthosilole organic photoelectric functional material and synthesis method thereof

A technology of photoelectric functional materials and organic photoelectric materials, which is applied in the direction of luminescent materials, silicon organic compounds, organic chemistry, etc., can solve the problems of harsh synthesis conditions of silicon-containing materials and limited research reports, and achieve simple methods, high stereoselectivity, The effect of high yield

Inactive Publication Date: 2017-03-29
TIANJIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the research reports on silicon-bridged acene ladder π-conjugated molecules, especially silicon-bridged acene biphenyl, are limited, and the synthesis conditions of silicon-containing substances are generally harsh, and the synthesis of such substances is a big challenge. and daunting task

Method used

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  • Dinaphthosilole organic photoelectric functional material and synthesis method thereof
  • Dinaphthosilole organic photoelectric functional material and synthesis method thereof
  • Dinaphthosilole organic photoelectric functional material and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Embodiment 1, the preparation of a dinaphthosilole organic photoelectric functional material, the steps are as follows:

[0024] Step 1, Synthesis of 1,2,4,5-tetraiodobenzene: Put 2.56g (11.2mmol) of periodic acid into a 250mL two-necked bottle, add 60mL of concentrated sulfuric acid while stirring, then slowly add 5.58g (33.6mmol ) KI, after 30 min, the temperature was lowered to 0° C., 1 mL (11.2 mmol) of benzene was slowly added thereto, and the reaction was carried out at room temperature for 24 hours. The reaction solution in the bottle was poured on ice, filtered, and washed with methanol to obtain a crude product. Recrystallized with 2-methoxyethanol to obtain 1,2,4,5-tetraiodobenzene with a yield of 71%.

[0025] Step 2, the synthesis of zirconium heterocyclopentadiene: under the protection of nitrogen, add 3.79g (13mmol) CpZr to the 200mL reaction tube 2 Cl 2 , and then added 50 mL of tetrahydrofuran, cooled to -78 ° C, added 10 mL (25 mmol) of n-butyllithiu...

Embodiment 2

[0032] Embodiment 2, the preparation of a dinaphthosilole organic photoelectric functional material, the steps are as follows:

[0033] Step 1, the synthesis method of 1,2,4,5-tetraiodobenzene is the same as that of Example 1.

[0034] Step 2, the synthesis of zirconium heterocyclopentadiene: under the protection of nitrogen, add 3.79g (13mmol) CpZr to the 200mL reaction tube 2 Cl 2 , and then added 50 mL of tetrahydrofuran, cooled to -78 ° C, added 10 mL (25 mmol) of n-butyllithium, and reacted at -78 ° C for 1 hour. Add 2.88 mL (20 mmol) of 4-octyne, return to room temperature, and stir for 3 hours to obtain zirconium cyclopentadiene.

[0035]Step 3. Synthesis of diiodonaphthalene b: Cool the zirconium heterocyclopentadiene to 0°C, add 1.18g (12mmol) cuprous chloride, 3.0ml (18mmol) DMPU and 10.56g (20mmol) 1,2,4 , 5-tetraiodobenzene, heat up to 50 ° C, react for 1 hour, add dilute hydrochloric acid to wash, add ether to extract, the organic phase is washed with saturated...

Embodiment 3

[0041] Embodiment 3, the preparation of a dinaphthosilole organic photoelectric functional material, the steps are as follows:

[0042] Step 1, synthesizing 1,2,4,5-tetraiodobenzene, the synthesis method is the same as that of Example 1.

[0043] Step 2, synthesizing zirconium heterocyclopentadiene, its synthetic method is identical with embodiment 2.

[0044] Step 3. Synthesis of diiodonaphthalene b: Cool the zirconium heterocyclopentadiene to 0°C, add 1.18g (12mmol) cuprous chloride, 6.336g (12mmol) DMPU, 1,2,4,5-tetraiodo Benzene, heat up to 50°C, react for 1 hour, add dilute hydrochloric acid to wash, add ether to extract, the organic phase is washed with saturated sodium bicarbonate solution, dried, filtered, and the solvent is removed by rotary evaporation. Separation and purification by column chromatography, using pure n-hexane as the eluent, yielded 1.83 g (yield 33.6%) of diiodonaphthalene b.

[0045] Step 4. Synthesis of binaphthalene b: under nitrogen protection,...

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Abstract

The invention discloses a dinaphthosilole organic photoelectric functional material. The functional material is synthesized mainly through the following steps: synthesizing a zirconium heterocycle performing water-free and oxygen-free reaction on bis-substituted internal alkyne under the catalytic action of a metallocene zirconium complex; under the catalytic action of cuprous chloride, reacting with tetraiodo-benzene to generate diiodo-naphthalene; synthesizing a dinaphthalene under the lithiation action of n-butyllithium; and finally synthesizing the dinaphthosilole photoelectric material under the lithiation action of tert-butyllithium. In the synthesis process, the method for preparing the diiodo-naphthalene through coupling reaction of heterocyclopentadiene and polyarylated iodide is simple and high in yield; through the activation action of the n-butyllithium, the dinaphthalene can be synthesized from the bimolecular diiodo-naphthalene; and the metallocene zirconium complex is used as a homogeneous olefin polymerization catalyst, so that the catalytic activity and the olefin polymerization stereoselectivity are high. The synthesized dinaphthosilole is of great use in the fields of conductive high-polymer materials, liquid crystal materials and biological active substances.

Description

technical field [0001] The invention relates to the field of organic photoelectric functional materials, in particular to a dinaphthosilole organic photoelectric functional material and a synthesis method thereof. Background technique [0002] With the application of organic photoelectric functional materials in various fields such as light-emitting diodes, solar cells, field effect transistors, electrical storage, and biochemical sensors, organic photoelectric functional materials have shown a rapid development trend in recent years. With the further development of organic optoelectronic functional materials, the difficulty of research mainly lies in the discovery and synthesis of π-conjugated molecules. In recent years, silicon-containing organic photoelectric functional materials have received extensive attention, and related studies have reported the synthesis of many novel and excellent organic photoelectric functional materials. Among them, silole is silacyclopentadie...

Claims

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Application Information

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IPC IPC(8): C07F7/08C09K11/06
CPCC07F7/0807C07F7/0827C09K11/06C09K2211/1096
Inventor 曲红梅张辉李君秋陈旭申海蛟
Owner TIANJIN UNIV
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