CN100509824C - Biphenyl(di-p-(5- pyrimidylethynyl)-phenyl)silane and synthetic method thereof - Google Patents
Biphenyl(di-p-(5- pyrimidylethynyl)-phenyl)silane and synthetic method thereof Download PDFInfo
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- CN100509824C CN100509824C CNB2007100427577A CN200710042757A CN100509824C CN 100509824 C CN100509824 C CN 100509824C CN B2007100427577 A CNB2007100427577 A CN B2007100427577A CN 200710042757 A CN200710042757 A CN 200710042757A CN 100509824 C CN100509824 C CN 100509824C
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- silane
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- ethynyl
- phenylbenzene
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Abstract
The present invention relates to biphenyl-[bis-para-(5-pyrimidinyl ethynyl)-phenyl] silane in the structure as shown. The compound is synthesized through the following steps: 1. reaction of biphenyl-(bis-para-5-ethynyl phenyl) silane and 5-bromo pyrimidine in tetrahydrofuran solvent under the action of palladium acetate, triphenyl phosphine, cuprous iodide and triethylamine, under stirring at 60-65 deg.c for 1-2 hr; and 2. vacuum distillation to eliminate solvent after reaction, and silica gel column chromatographic separation to obtain yellowish solid biphenyl-[bis-para-(5-pyrimidinyl ethynyl)-phenyl] silane product. The present invention has the advantages of simple operation, mild condition, high yield, etc.
Description
Technical field
The present invention relates to the adulterated tetraphenyl silane of a kind of pyrimidine and synthetic method, particularly phenylbenzene (two pairs-(5-pyrimidine ethynyl)-phenyl) silane and synthetic method thereof.
Background technology
In recent years, electroluminescent device of organic thin film has huge application potential owing to have advantages such as luminous efficiency height, rich color, simple in structure and driving voltage are low in flat pannel display and backlight field, has obtained research extensively and profoundly.In the multilayered structure of OLED, organosilicon polymer Chang Zuowei hole transmission layer.It is reported that the tetraphenyl-silicon alkane derivatives can be used as the OLED blue light emitting material, the adulterated alkynyl benzene of pyrimidine class thread-like molecule also has good blue light emitting character.
Because silicon has the 3d unoccupied orbital, the πDian Zi of delocalization aryl, alkynyl, heteroaryl etc. effectively, this makes silicoorganic compound have unique physics and chemical property, show material properties such as special electroconductibility and optical activity, have great application prospect at aspects such as semi-conductor, light LED materials.
Summary of the invention:
One of purpose of the present invention is to provide a kind of phenylbenzene (two pairs-(5-pyrimidine ethynyl)-phenyl) silane
Two of purpose of the present invention is to provide the synthetic method of this compound.
For achieving the above object, the reaction mechanism that the inventive method adopts is:
According to above-mentioned reaction mechanism, the present invention adopts following technical scheme:
A kind of phenylbenzene (two pairs-(5-pyrimidine ethynyl)-phenyl) silane is characterized in that the structure of this compound is:
The physical parameter of this compound:
Molecular formula: C
36H
24N
4Si
Structural formula:
Chinese named: phenylbenzene (two pairs-(5-pyrimidine ethynyl)-phenyl) silane
English name: diphenylbis (4-(pyrimidin-5-ylethynyl) phenyl) silane
Molecular weight: 540.69
Outward appearance: light yellow solid
Fusing point: 119～121 ℃
Proton nmr spectra (500MHz, CDCl
3): δ: 9.156 (s, 2H), 8.872 (s, 4H), 7.599-7.534 (m, 12H), 7.498-7.466 (m, 2H), 7.432-7.401 (m, 4H)
Carbon-13 nmr spectra (125MHz, CDCl
3): δ: 159.05,157.14,136.71,136.66,136.16,133.21,131.40,130.45,128.52,123.48,120.16,96.50,83.73;
Infrared spectra (KBr, υ max): 3066,2219,1632,1592,1540,1490cm
-1
Mass spectrum (EI, m/z): 540 (M
+), 463,386,361.
The synthetic method of above-mentioned phenylbenzene (two to (5-pyrimidine ethynyl) phenyl) silane, it is characterized in that these method concrete steps are as follows: phenylbenzene (two pairs of acetylene phenyl) silane, 5-bromo pyrimi piperidine and the triethylamine mol ratio by 1.00:2.10～5.00:1.00～15.00 is dissolved in the tetrahydrofuran (THF), the palladium, triphenylphosphine and the cuprous iodide that add catalyst levels again, be heated to 60～65 ℃, stirring reaction 1～2 hour; Reaction finishes the back underpressure distillation except that desolvating, and promptly gets faint yellow solid phenylbenzene (two pairs-(5-pyrimidine ethynyl)-phenyl) silane through silica gel column chromatography.
Phenylbenzene of the present invention (two to (5-pyrimidine ethynyl) phenyl) silane, owing to contain pyrimidine heterocyclic and alkynyl benzene skeleton in its molecular structure, it is the adulterated aryl-silane of a kind of novel pyrimidine with big pi-conjugated system, should have favorable conductive and luminescent properties, be a kind of potential electroluminescent material.
That the inventive method has is simple to operate, mild condition, productive rate advantages of higher.
Embodiment:
Embodiment one: in 25mL single port bottle; add 30mg phenylbenzene (two pairs of acetylene phenyl) silane, 30mg5 bromo pyrimi piperidine, 1.8mg palladium, 4.0mg triphenylphosphine, 0.8mg cuprous iodide, 22 μ L triethylamines, 5mL tetrahydrofuran (THF); be heated to 60～65 ℃ under the nitrogen protection; stirred 1 hour; filter the back underpressure distillation except that desolvating; through purification by silica gel column chromatography; developping agent is sherwood oil and the ethyl acetate volume ratio mixed solvent by 2:1; obtain 30mg phenylbenzene (two pairs-(5-pyrimidine ethynyl)-phenyl) silane, productive rate 71%.
Embodiment two: in 100mL single port bottle, add 300mg phenylbenzene (two pairs of acetylene phenyl) silane, 400mg5-bromo pyrimi piperidine, 30mg palladium, 70mg triphenylphosphine, 12mg cuprous iodide, 300 μ L triethylamines, 30mL tetrahydrofuran (THF); Be heated to 60～65 ℃ under the nitrogen protection, stirred 1 hour, filter the back underpressure distillation except that desolvating; through purification by silica gel column chromatography; developping agent be sherwood oil and ethyl acetate by the volume ratio mixed solvent of 2:1, obtain 291mg phenylbenzene (two pairs-(5-pyrimidine ethynyl)-phenyl) silane, productive rate 69%.
Embodiment three: in 250mL single port bottle, add 3g phenylbenzene (two pairs of acetylene phenyl) silane, 5g5-bromo pyrimi piperidine, 350mg palladium, 820mg triphenylphosphine, 100mg cuprous iodide, 3.5mL triethylamine, 60mL tetrahydrofuran (THF); Be heated to 60～65 ℃ under the nitrogen protection, stirred 2 hours, filter the back underpressure distillation except that desolvating; through purification by silica gel column chromatography; developping agent be sherwood oil and ethyl acetate by the volume ratio mixed solvent of 2:1, obtain 2.86g phenylbenzene (two pairs-(5-pyrimidine ethynyl)-phenyl) silane, productive rate 68%.
Claims (2)
1. a phenylbenzene (two pairs-(pyrimidine-5-base-ethynyl)-phenyl) silane is characterized in that the structure of this compound is:
2. the synthetic method of a phenylbenzene according to claim 1 (two pairs-(pyrimidine-5-base-ethynyl)-phenyl) silane, it is characterized in that this method has following steps: phenylbenzene (two pairs of acetylene phenyl) silane, 5-bromo pyrimi piperidine and the triethylamine mol ratio by 1.00:2.10～5.00:1.00～15.00 is dissolved in the tetrahydrofuran (THF), the palladium, triphenylphosphine and the cuprous iodide that add catalyst levels again, be heated to 60～65 ℃, stirring reaction 1～2 hour; Reaction finishes the back underpressure distillation except that desolvating, and promptly gets faint yellow solid phenylbenzene (two pairs-(pyrimidine-5-base-ethynyl)-phenyl) silane through silica gel column chromatography.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100427577A CN100509824C (en) | 2007-06-26 | 2007-06-26 | Biphenyl(di-p-(5- pyrimidylethynyl)-phenyl)silane and synthetic method thereof |
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|---|---|---|---|
| CNB2007100427577A CN100509824C (en) | 2007-06-26 | 2007-06-26 | Biphenyl(di-p-(5- pyrimidylethynyl)-phenyl)silane and synthetic method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101077876A CN101077876A (en) | 2007-11-28 |
| CN100509824C true CN100509824C (en) | 2009-07-08 |
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| CNB2007100427577A Expired - Fee Related CN100509824C (en) | 2007-06-26 | 2007-06-26 | Biphenyl(di-p-(5- pyrimidylethynyl)-phenyl)silane and synthetic method thereof |
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2007
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Granted publication date: 20090708 Termination date: 20120626 |