PL430584A1 - 1,2-difenylobenzo[1,2-j]koronen oraz sposób jego otrzymywania - Google Patents
1,2-difenylobenzo[1,2-j]koronen oraz sposób jego otrzymywaniaInfo
- Publication number
- PL430584A1 PL430584A1 PL430584A PL43058419A PL430584A1 PL 430584 A1 PL430584 A1 PL 430584A1 PL 430584 A PL430584 A PL 430584A PL 43058419 A PL43058419 A PL 43058419A PL 430584 A1 PL430584 A1 PL 430584A1
- Authority
- PL
- Poland
- Prior art keywords
- diphenylbenzo
- mixture
- mmol
- perylene
- coronene
- Prior art date
Links
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 title abstract 8
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 abstract 4
- ZMABPNOKZBGINZ-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(C=2C=3C4=C1C=CC1=CC=CC(C5=CC=CC(=CC=2)C=35)=C14)C1=CC=CC=C1 Chemical group C1(=CC=CC=C1)C1=C(C=2C=3C4=C1C=CC1=CC=CC(C5=CC=CC(=CC=2)C=35)=C14)C1=CC=CC=C1 ZMABPNOKZBGINZ-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 abstract 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 abstract 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 abstract 1
- -1 2 -trimethylsilylphenyl Chemical group 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 230000005526 G1 to G0 transition Effects 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 238000006352 cycloaddition reaction Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 abstract 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000011555 saturated liquid Substances 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 abstract 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem wynalazku jest 1,2-difenylobenzeno[1,2-j]koronen przedstawiony wzorem 1. Istotę wynalazku stanowi również sposób otrzymywania 1,2-difenylobenzo[1,2-j]koronenu przedstawionego wzorem 1, polegający na tym, że do odizolowanego od dostępu światła reaktora wprowadza się 1,2-difenylobenzo[ghi]perylen, mieszaninę stopionego sukcynonitrylu z 1,2-dimetoksyetanem w stosunku objętościowym mieszaniny od 3:1 do 1:3, w ilości od 5 do 20 ml tej mieszaniny na 1 mmol 1,2-difenylobenzo[ghi]perylenu, oraz reagent generujący aryn w postaci fluorku cezu w ilości od 2 do 8 mmoli na 1 mmol 1,2-difenylobenzo[ghi]perylenu, następnie do mieszaniny reakcyjnej wprowadza się prekursor benzynu w postaci triflatu 2-trimetylosililofenylu w ilości od 2 do 8 mmoli na 1 mmol 1,2-difenylobenzo[ghi]perylenu, po czym zawartość reaktora miesza się w temperaturze od 40 do 100°C, w atmosferze gazu obojętnego, przez co najmniej 12 godzin. Korzystnie, po zakończeniu reakcji cykloaddycji, chłodzi się zawartość reaktora do temperatury nie wyższej niż 50°C i odparowuje lotne frakcje, zaś pozostałość przemywa się kilka razy ciekłym, nasyconym węglowodorem alifatycznym, następnie kilka razy wodą, po czym przeprowadza się dalsze oczyszczanie metodą chromatografii kolumnowej w układzie faz normalnych, gdzie faza stacjonarna to żel krzemionkowy, faza ruchoma to mieszanina rozpuszczalników, a mianowicie nasyconego, ciekłego węglowodoru z chlorkiem metylenu w stosunku objętościowym od 10 do 1 do 1 do 10, otrzymując w efekcie czysty produkt w postaci 1,2-difenylobenzo[1,2-j]koronenu.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL430584A PL238584B1 (pl) | 2019-07-13 | 2019-07-13 | 1,2-difenylobenzo[1,2-j]koronen oraz sposób jego otrzymywania |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL430584A PL238584B1 (pl) | 2019-07-13 | 2019-07-13 | 1,2-difenylobenzo[1,2-j]koronen oraz sposób jego otrzymywania |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL430584A1 true PL430584A1 (pl) | 2021-01-25 |
| PL238584B1 PL238584B1 (pl) | 2021-09-13 |
Family
ID=74222267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL430584A PL238584B1 (pl) | 2019-07-13 | 2019-07-13 | 1,2-difenylobenzo[1,2-j]koronen oraz sposób jego otrzymywania |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL238584B1 (pl) |
-
2019
- 2019-07-13 PL PL430584A patent/PL238584B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL238584B1 (pl) | 2021-09-13 |
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