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Synthetic method of tetracene and pentacene compounds

A synthetic method and compound technology, which is applied in the field of synthesizing aryl-substituted or alkyl-substituted naphthacene and pentacene compounds, can solve the problems of large substrate limitations, low yield, and many steps, and achieve operational Convenience, high yield, and mild reaction conditions

Active Publication Date: 2016-03-02
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the methods have disadvantages such as many steps, low yield, great limitation on the substrate, and difficulty in introducing specific substituents at multiple positions on the tetracene or pentacene rings.

Method used

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  • Synthetic method of tetracene and pentacene compounds
  • Synthetic method of tetracene and pentacene compounds
  • Synthetic method of tetracene and pentacene compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of 5,12-diaryltetracene (5,12-diaryltetracene) from o-phthalaldehyde, phenylacetylene, and arylboronic acid

[0026] 1) Synthesis of raw material bispropargyl carbonate 1a

[0027]

[0028] Under the protection of argon, add phenylacetylene (120mmol, 13.2mL) and tetrahydrofuran (120mL) sequentially to a dry 250mL three-neck flask with a stirring bar, then cool to -78°C in a dry ice / acetone bath, and slowly add 2.5M n-Butyllithium / n-hexane solution (110mmol, 44mL), the dropwise addition was completed, and after stirring for 30 minutes, o-phthalaldehyde (50mmol, 6.71g) was added, reacted for 2 hours, and TLC detected that the reaction was completed; saturated NH 4 Quenched with Cl solution, extracted with ethyl acetate, anhydrous Na 2 SO 4 Dry, filter, spin dry, and separate by silica gel column chromatography, eluent: petroleum ether: acetone = 5:1, to obtain 17.03 g of yellow viscous liquid, yield 100%.

[0029]Add the diol (5mmol, 1.7g), dich...

Embodiment 2

[0033] Example 2: Synthesis of 5-phenyl-12-(p-chlorophenyl)naphthacene (5-(4-Chlorophenyl)-12-phenyltetracene)

[0034]

[0035] Under argon protection, bispropargyl carbonate 1a (0.2mmol, 91mg), p-chlorophenylboronic acid (0.8mmol, 125.1mg) and tetrahydrofuran (5mL) were successively added into a 25mL Schlenk reaction tube with a stirring bar to dissolve, and added Tetrakistriphenylphosphine palladium (0.01mmol, 12mg), react at 100°C for 3h, TLC detects that the reaction is complete; wash the reaction solution into a 100mL egg-shaped bottle with ethyl acetate, add an appropriate amount of silica gel, spin dry, and separate by silica gel column chromatography , 78.1mg of yellow solid was obtained, the yield was 94%. Melting point, 181-183°C; 1 HNMR (400MHz, CDCl 3 )δ8.31(s,1H),8.26(s,1H),7.77-7.75(m,2H),7.68-7.59(m,7H),7.53(d,J=6.0Hz,2H),7.47(d ,J=8.0Hz,2H),7.29-7.20(m,4H). 13 CNMR (100.6MHz, CDCl 3 )δ139.11,137.73,137.47,135.40,133.65,132.88,131.44,131.07,130.95,129.3...

Embodiment 3

[0036] Example 3: Synthesis of 5-phenyl-12-(p-trifluoromethylphenyl)naphthacene (5-phenyl-12-(4-(trifluoromethyl)phenyl)tetracene)

[0037]

[0038] Under argon protection, bispropargyl carbonate 1a (0.2mmol, 91mg), p-trifluoromethylphenylboronic acid (0.8mmol, 152mg) and tetrahydrofuran (5mL) were successively added into a 25mL Schlenk reaction tube with a stirrer to dissolve , add tetrakistriphenylphosphine palladium (0.01mmol, 12mg), react at 100°C for 3h, TLC detects that the reaction is complete; wash the reaction solution into a 100mL egg-shaped bottle with ethyl acetate, add an appropriate amount of silica gel, spin dry, and use silica gel column After chromatographic separation, 69.2 mg of yellow solid was obtained, with a yield of 77%. Melting point, 181-182°C; 1 HNMR (400MHz, CDCl 3 )δ8.32(s,1H),8.18(s,1H),7.92(d,J=8.0Hz,2H),7.79-7.76(m,2H),7.70-7.52(m,9H),7.30-7.23 (m,4H). 13 CNMR (100.6MHz, CDCl 3 )δ143.37(q, 5 J C-F =1.1Hz),139.02,137.84,135.01,131.96,13...

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Abstract

The invention relates to a synthesis method of tetracene and pentacene compounds. A plurality of double-acetylene propanol carbonate compounds are prepared from simple and available phthalic dicarboxaldehyde compound and aryl acetylene by using addition reaction of an alkynyl lithium reagent. The double-acetylene propanol carbonate compounds can react with an organic boronic acid in series in the presence of a catalytic amount of palladium reagent, so as to further synthetize the tetracene and pentacene compounds at good to excellent yield. The method has the characteristics of being available in raw materials, simple to operate, mild in condition, convenient and fast, excellent in yield and the like, and aryl and alkyl can be effectively led to skeletons of tetracene and pentacene by using the method.

Description

technical field [0001] The invention relates to a method for synthesizing substituted tetracene and pentacene by transition metal palladium catalysis, which is mainly used for synthesizing aryl-substituted or alkyl-substituted naphthacene and pentacene compounds simply and efficiently. Background technique [0002] Aromatic chemistry is an important part of the whole organic chemistry, and it is also the main building block of molecular engineering, crystal engineering, drug design, molecular electronics, and inorganic and organometallic chemistry. With the continuous development of material science research, polycyclic aromatic hydrocarbons have gradually become a hot spot in the research of organic materials. Due to the high delocalization of π electrons in their conjugated systems, polyphenyl aromatic fused ring compounds show good performance in many functional materials, such as photoluminescent materials, photosensitizers, organic superconducting materials, and liquid ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C15/62C07C1/32C07C25/22C07C22/08C07C17/26C07C43/205C07C43/225C07C41/30C07D333/16C07D333/12
Inventor 刘元红陈铭陈宜峰
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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