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Boron-nitride doped coronene compound and preparation method thereof

A compound and boron nitrogen technology, which is applied in the field of polycyclic aromatic hydrocarbon compounds and their preparation, can solve the problems of inability to synthesize alkoxy-free boron nitride compounds, unfavorable derivative expansion of conjugated systems, limited application and the like, and achieves short synthesis steps. , easy to operate, less environmental pollution

Inactive Publication Date: 2017-09-15
SHANGHAI UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

But above-mentioned method can only synthesize the borazine compound that hexaalkoxy group replaces, and can't synthesize the borazine compound that does not have alkoxy group replacement
Due to the presence of alkoxy groups, some intrinsic properties of boronazide compounds will inevitably be changed. For example, the solid accumulation of this type of compound lacks strong intermolecular π force, and the strong force is polycyclic aromatic hydrocarbons. As an extremely important prerequisite for electronic materials, it limits its application in molecular devices; at the same time, these alkoxy groups are also not conducive to the derivative expansion of further conjugated systems

Method used

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  • Boron-nitride doped coronene compound and preparation method thereof
  • Boron-nitride doped coronene compound and preparation method thereof
  • Boron-nitride doped coronene compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Example 1: 1,5,9-Triaza-2,6,10-triphenylboronidine

[0022]

[0023] 218.7 mg of triamine-based compound, the preparation method is referred to Chem. Commun. 2016, 52, 537-540, dissolved in o-dichlorobenzene (22 mL), 508.2 mg of phenyldichloroboron, 485.7 mg of triethylamine were added under nitrogen, and refluxed 24h. After the reaction, the o-dichlorobenzene was evaporated under reduced pressure, and then the solvent was evaporated. The mixed solvent with a volume ratio of petroleum ether and dichloromethane of 1:1 was used as the eluent to separate by silica gel column chromatography to obtain a white solid compound 1,5. ,9-triazide-2,6,10-triphenylboronidine 261mg, the yield is 61%, melting point: >300℃.

[0024] The obtained 1,5,9-triaza-2,6,10-triphenylboronidine was characterized as follows: IR (KBr, cm -1 ): 3385, 3044, 1599, 1484, 1422, 1328, 1247, 700; 1 H NMR (500MHz, CDCl 3 ):δ8.77(d,J=8.0Hz,3H),8.42(s,3H),8.03(dd,J=7.8Hz,1.5Hz,6H),7.86(d,J=8.0Hz,3H),...

Embodiment 2

[0025] Example 2: 1,5,9-Triaza-2,6,10-tris(4-methylphenyl)boronidine

[0026]

[0027] Adopt a synthetic method similar to Example 1, replace phenylboron dichloride with equimolar 4-methylphenylboron dichloride (refer to J.Org.Chem.2000,65,9125-9128 for preparation method), The ratio of the eluent was adjusted to 2:1, and other steps were the same as in Example 1 to obtain a white solid compound 1,5,9-triaza-2,6,10-tris(4-methylphenyl)boronidine 258.2mg , its yield is 56%, melting point: >300 ℃.

[0028] The obtained 1,5,9-triaza-2,6,10-tris(4-methylphenyl)boronidine was characterized as follows: IR(KBr,cm -1 ): 3741, 3385, 3008, 1599, 1422, 1324, 815; 1 H NMR (500MHz, CDCl 3 )δ8.70(d, J=7.9Hz, 3H), 8.27(s, 3H), 7.91(d, J=7.5Hz, 6H), 7.75(d, J=8.0Hz, 3H), 7.44(d, J=7.4Hz, 6H), 2.54(s, 9H); 13C NMR (125 MHz, CDCl 3 )δ141.0,138.8,136.7,135.4,134.5,133.9,129.2,123.9,116.9,115.8,21.8; 11 B NMR (160MHz, CDCl 3 ):δ35.9; HRMS(DART Positive)m / z calcd forC 39 H 31 10 B 3...

Embodiment 3

[0029] Example 3: 1,5,9-Triaza-2,6,10-tris(4-trifluoromethylphenyl)boronidine

[0030]

[0031] The synthesis method similar to Example 1 was adopted, and equimolar 4-trifluoromethylphenylboron dichloride was used for phenylboron dichloride (refer to J.Org.Chem. 2000, 65, 9125-9128 for the preparation method) Replacement, other steps are the same as in Example 1, to obtain a pale yellow solid compound 1,5,9-triazide-2,6,10-tris(4-trifluoromethylphenyl)boronidine 352.2mg, its yield is 54%, melting point: >300 ℃.

[0032] The obtained 1,5,9-triazide-2,6,10-tris(4-trifluoromethylphenyl)boronamidine was characterized as follows: IR (KBr, cm -1 ): 3402, 3038, 1599, 1327, 1118, 1063, 828, 695; 1 H NMR (500MHz, CD 3 COCD 3 ): δ9.68(s,3H),8.28(d,J=7.9Hz,3H),8.02(d,J=7.4Hz,6H),7.84(d,J=7.9Hz,3H),7.80(d ,J=7.5Hz,6H); 19 F NMR (470MHz, CD 3 COCD 3 ):δ-62.9(s,CF 3 ); 13 C NMR (125MHz, CD 3 COCD 3 ): δ145.6,141.7,135.6, 134.9,134.2,130.5(q, 2 J C-F =31.6Hz), 125.8(q, 1 J ...

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Abstract

The invention relates to a boron-nitrogen doped pine compound and a preparation method thereof. The structural formula of the compound is: in the formula, R is phenyl, methylphenyl, tert-butylphenyl, trifluoromethylphenyl, bis(trifluoromethyl)phenyl, mesityl, naphthyl, etc.; R' is H, C4-C18 alkyl, phenyl, methylphenyl, methoxyphenyl, fluorophenyl, trifluoromethylphenyl, tert-butylphenyl, naphthyl, benzyl, ring Hexyl, pyridyl, thienyl or 2,4,6-trimethylphenyl, etc. The boron-nitrogen-doped pine compound of the present invention has good thermal stability, and the fluorescence emission spectrum in an organic solvent has strong fluorescence in the range of 380-500 nm, and its band gap can be opened after boron-nitrogen doping , and has great application prospects in the fields of hydrogen storage, biomedicine, coordination chemistry, catalysis, and electronic devices.

Description

technical field [0001] The invention relates to a polycyclic aromatic hydrocarbon compound and a preparation method thereof, in particular to a boron-nitrogen doped pinamidine compound and a preparation method thereof. Background technique [0002] Polycyclic aromatic hydrocarbons (PAHs) are aromatic compounds formed by the coupling of 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. It has important research value in supramolecular, electrical conductivity, 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 crys...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/02
Inventor 谭启涛张涛夏怀达陈欢欢刘秉新许斌
Owner SHANGHAI UNIV
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