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Method for preparing benzogermanole compound through naphthyl lithium induced intramolecular cyclization reaction, product and application

A technology of benzogermanole and compound, which is applied in the field of naphthalene lithium-induced intramolecular cyclization reaction to prepare benzogermanole compound, which can solve the problems of low practical value and poor atom economy, and achieve high-efficiency solid-state luminescence and simple storage , The effect of material structure stability

Pending Publication Date: 2022-04-19
HANGZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The first object of the present invention is to provide a method for preparing benzogermanole by intramolecular cyclization reaction, which can overcome the problems of poor atom economy and low practical value of the original method without noble metal catalysis. , providing a method for synthesizing benzogermanole compounds with low cost, mild reaction conditions and high yield

Method used

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  • Method for preparing benzogermanole compound through naphthyl lithium induced intramolecular cyclization reaction, product and application
  • Method for preparing benzogermanole compound through naphthyl lithium induced intramolecular cyclization reaction, product and application
  • Method for preparing benzogermanole compound through naphthyl lithium induced intramolecular cyclization reaction, product and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the synthesis of benzogermanole compound 2:

[0041]

[0042] A mixture of particulate lithium metal (28 mg, 4.0 mmol) and naphthalene (512 mg, 4.0 mmol) in THF (4 mL) was stirred at room temperature under an argon atmosphere for 5 hours to give a solution of LiNaph in tetrahydrofuran.

[0043] 2 mL of a solution of LiNaph in THF was added to a solution of compound 1 (282 mg, 1 mmol) in THF (2 mL) under argon atmosphere at 0°C. After stirring for 5 min, the reaction mixture was washed with H 2 O quenching. The mixture was washed with CH 2 Cl 2 The extract was dried over sodium sulfate, and concentrated under reduced pressure. The product was purified by column chromatography using petroleum ether (PE) as eluent to afford 203 mg of compound 2 as a white solid, yield 72%. Compound 2: 1 HNMR (400MHz, CD 2 Cl 2 )δ7.56-7.48(m,4H),7.38-7.30(m,4H),7.26-7.20(m,2H),0.65(s,6H). 13 CNMR (100MHz, CDCl 3 )δ148.25,147.83,140.79,139.56,137.99,132.02,129.48,1...

Embodiment 2

[0044] Embodiment 2: the synthesis of benzogermanole compound 3:

[0045]

[0046] Same as Example 1, except that compound 1 was replaced by compound 3, and the obtained product, benzogermanole compound 4, was a white solid with a yield of 75%. 1 HNMR (400MHz, CD 2 Cl 2)δ7.54(d,J=4Hz,1H),7.44-7.40(m,3H),7.31-7.30(m,2H),7.20-7.16(m,1H),6.92-6.90(m,2H), 3.82(s,3H),0.64(s,6H). 13 C NMR (100MHz, CDCl 3 )δ159.11,148.58,147.23,140.42,135.89,132.26,131.97,129.46,127.99,126.55,124.82,114.36,55.48,-2.09.HRMS-ESI:m / z:calcd.for C 17 h 19 GeO([M+H] + ):313.0645. Found: 313.0635.

Embodiment 3

[0047] Embodiment 3: the synthesis of benzogermanole compound 6:

[0048]

[0049] Same as Example 1, except that compound 1 was replaced by compound 5, and the obtained product, benzogermanole compound 6, was a light yellow solid with a yield of 89%. 1 H NMR (400MHz, Acetone-d 6 )δ7.57-7.55(m,1H),7.43-7.39(m,3H),7.28-7.27(m,2H),7.15-7.11(m,1H),6.75(d,J=4Hz,2H), 2.97(s,6H),0.62(s,6H). 13 C NMR (100MHz, CDCl 3 )δ149.07,147.66,140.23,133.66,131.91,129.40,127.91,126.04,124.42,112.76,40.68,-1.99.HRMS-ESI:m / z:calcd.for C 18 h 22 GeN([M+H] + ):326.0962. Found: 326.0965.

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Abstract

The invention discloses a method for preparing a benzogermanole compound through naphthyl lithium induced intramolecular cyclization reaction, a product and application. The method mainly comprises the following steps of: reacting lithium naphthyl with (o-germanium phenyl) acetylene in tetrahydrofuran or diethyl ether at the temperature of between-78 and 0 DEG C for 5 to 30 minutes to generate a lithiated benzogermanle intermediate; and further carrying out Negishi coupling reaction with an electrophilic reagent, and separating by a chromatographic column to obtain a series of functional germanium-containing conjugated molecules containing the benzogermanle structure. Through selection of aryl substituent groups, the light-emitting wavelength of the benzogermanole compound is regulated and controlled, and high-purity and high-quantum-yield blue light emission is realized. The method is simple, efficient, wide in substrate range and easy to functionalize. The method has the advantages of mild reaction conditions, simple operation, atom economy and easy industrialization.

Description

technical field [0001] The invention relates to the technical fields of fine chemical industry and organic synthesis, in particular to a method for preparing a benzogermanole compound through an intramolecular cyclization reaction induced by naphthyl lithium. Background technique [0002] In recent years, efforts have been made to develop novel π-conjugated materials containing main group elements such as silicon, boron, nitrogen, phosphorus, and sulfur, including small molecules, oligomers, and polymers. These hybrid organic light-emitting materials are widely used in many fields such as organic field-effect transistors, organic photovoltaics, organic light-emitting diodes, biological imaging and labeling, and tumor photodiagnosis and treatment. Among them, silicon has empty 3d orbitals, and the orbital energy of functional molecules can be adjusted through the interaction of silicon σ electrons and conjugated systems. Therefore, silicon-containing π-conjugated systems (suc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/30C09K11/06
CPCC07F7/30C09K11/06C09K2211/1096C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1033C09K2211/1029C09K2211/1092
Inventor 卢华项小双周志宽
Owner HANGZHOU NORMAL UNIVERSITY
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