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1, 5, 9-trisubstituted coronene compound and synthesis method thereof

A compound and three-substitution technology, which is applied in the field of polycyclic aromatic hydrocarbons and their preparation, can solve the problems of single structure, harsh conditions, and low yield in the synthesis of perone, and achieve the effects of short synthesis steps, less environmental pollution, and convenient operation

Active Publication Date: 2017-04-19
SHANGHAI UNIV
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis methods of perone are currently reported, some methods have long steps, harsh conditions, low yield, and some have a single structure of synthetic perone
Although there are many synthetic methods of the parent perone, the 1,5,9-one has not been reported yet.

Method used

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  • 1, 5, 9-trisubstituted coronene compound and synthesis method thereof
  • 1, 5, 9-trisubstituted coronene compound and synthesis method thereof
  • 1, 5, 9-trisubstituted coronene compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Taking the synthesis of 1,5,9-tri(p-methylphenyl)cone as an example, its structural formula is as follows:

[0032]

[0033] The raw materials used and their synthetic methods are:

[0034] 1. Synthesis of 1,5,9-triiodotriphenylene

[0035] Dissolve 2g of 1,5,9-triaminotriphenylene (refer to Chem.Commun.2016,52,537-540 for the preparation method) in hydrochloric acid solution (30mL water, 15mL hydrochloric acid), cool to 0°C in an ice-salt bath, and use a constant Add 20mL of 1M sodium nitrite aqueous solution dropwise into the pressure dropping funnel. After the dropwise addition, stir in an ice-salt bath for 1 h, then pour 30 mL of a 1.5 M potassium iodide aqueous solution, and react at 65°C until the foam disappears and a black solid is formed. After cooling and suction filtration, the solid was washed successively with water, sodium thiosulfate solution, water and ethanol again. The solid was dissolved in 200 mL of THF, and the filtrate was obtai...

Embodiment 2

[0041] Embodiment 2: Taking the synthesis of 1,5,9-tris(p-methoxyphenyl)cone as an example, its structural formula is as follows:

[0042]

[0043] The raw materials used and the synthesis method are:

[0044] In step 2 of this embodiment, p-methylphenylacetylene is replaced with equimolar p-methoxyphenylacetylene, and other steps of this step are the same as in Example 1. The eluent ratio in all steps is adjusted to 1:1, other steps are the same as in Example 1, a yellow solid 1,5,9-tris(p-methoxyphenyl)cone is prepared, and its yield is: 19 %, melting point: 141-143°C.

[0045] The characterization data of the resulting product are as follows:

[0046] 1 H NMR (500MHz, CDCl 3 ): δ9.01(d, J=8.6Hz, 3H), 8.85(d, J=8.8Hz, 3H), 8.83(s, 3H), 7.85(d, J=8.3Hz, 6H), 7.24(d ,J=8.3,6H),4.02(s,9H); 13 C NMR (125MHz, CDCl 3 ): δ159.3, 138.8, 133.9, 132.0, 128.4, 127.4, 126.9, 126.1, 125.0, 123.3, 122.2, 114.1, 55.6; HRMS (DART) calcd for C 45 h 31 o 3 [M+H] + 619.2268,found...

Embodiment 3

[0047] Embodiment 3: Taking the synthesis of 1,5,9-tributylcone as an example, its structural formula is as follows:

[0048]

[0049] The raw materials used and the synthesis method are:

[0050] In step 2 of this example, 1g of 1,5,9-triiodotriphenylene, 57mg of bis(triphenylphosphine)palladium dichloride, 12.6mg of cuprous iodide, 488mg of 1-hexyne were added to the flask, 50 mL of triethylamine, the molar ratio of 1,5,9-triiodotriphenylene, bis(triphenylphosphine)palladium dichloride, cuprous iodide and 1-hexyne is 1:0.05:0.04:3.6. Under the protection of inert gas, react at 50°C for 12h. Then the solvent was evaporated, and the mixed solvent of petroleum ether and dichloromethane with a volume ratio of 10:1 was used as an eluent to separate by silica gel column chromatography to obtain light yellow oily liquid 1,5,9-trihexynetriphenylene, which produced Rate: 51%.

[0051] In step 3 of this example, 1,5,9-hexynyltriphenylene and 1,8-diazabicycloundec-7-ene were adde...

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Abstract

The present invention relates to a 1, 5, 9-trisubstituted coronene compound and a synthesis method thereof. The structural formula of the compound is shown in img file = 'dest _ path _ image 001. TIF 'wi = '109 'he = '108', wherein R represents H, C1-C18 alkyl, phenyl, 4-methylphenyl, 4-methoxy phenyl, benzyl, cyclohexyl, 4-trifluoromethylphenyl, thiophene, furan and the like. According to the technical scheme of the invention, the easily prepared 1, 5, 9-triamido triphenylene is subjected to diazotization and halogenation reaction to obtain the tri-halogenated triphenylene. After that, the tri-halogenated triphenylene is subjected to Sonogashira reaction with various alkynes to generate atriyne-triphenylene compounds. Finally, through the metal-catalyzed reaction and the cyclization reaction under the effect of an organic base, various 1, 5, 9-trisubstituted coronene compounds, novel in structure, can be obtained. According to the technical scheme of the invention, raw materials are easy for mass preparation. Meanwhile, the synthesis step is relatively short and the operation is convenient. The obtained trisubstituted coronene compound is good in thermal stability and chemical stability, and the trisubstituted coronene emits the relatively strong fluorescence within the range of 420-550 nm according to the fluorescence emission spectrum of the trisubstituted coronene compound. Therefore, the trisubstituted coronene is an excellent fluorescent material for preparing UV ultraviolet charge-coupled devices (UV-CCD) and organic light-emitting diodes (OLEDs), and has a wide application prospect in the field of electronic materials.

Description

technical field [0001] The invention relates to a polycyclic aromatic hydrocarbon compound and a preparation method thereof, in particular to a 1,5,9-trisubstituted pine compound and a preparation method thereof. Background technique [0002] Polycyclic aromatic hydrocarbons (PAHs) are aromatic compounds formed by coupling two or more six-membered benzene rings with two adjacent carbon atoms. The π electrons of fused-ring aromatic hydrocarbons are delocalized in the molecule. Due to the large conjugated system, the π-π interaction between molecules is strong, and its mechanical properties, magnetic properties, thermodynamic properties and electrical properties are unique, making it It has important research value in supramolecular, electrical conduction, superconductivity, magnetism, optical properties, photoelectric conversion, etc., and has broad application prospects in the field of electronic materials (field effect transistors, photodiodes, solar cells, liquid crystal m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/20C07C2/48C07C43/205C07C41/30
CPCC07C15/20C07C43/205
Inventor 谭启涛夏怀达周丹丹刘秉新许斌
Owner SHANGHAI UNIV
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