PL430592A1 - Method of naphtho-, anthraceno- and phenanthro[1,2,3,4-ghi]perylenes preparation - Google Patents
Method of naphtho-, anthraceno- and phenanthro[1,2,3,4-ghi]perylenes preparationInfo
- Publication number
- PL430592A1 PL430592A1 PL430592A PL43059219A PL430592A1 PL 430592 A1 PL430592 A1 PL 430592A1 PL 430592 A PL430592 A PL 430592A PL 43059219 A PL43059219 A PL 43059219A PL 430592 A1 PL430592 A1 PL 430592A1
- Authority
- PL
- Poland
- Prior art keywords
- perylene
- mmol
- phenanthro
- ghi
- several times
- Prior art date
Links
- VUFURXZETIQKNL-UHFFFAOYSA-N octacyclo[20.8.0.02,11.03,8.04,29.012,21.013,18.025,30]triaconta-1,3(8),4,6,9,11,13,15,17,19,21,23,25(30),26,28-pentadecaene Chemical class C1=CC=C2C=CC3=C4C5=CC=CC=C5C=CC4=C(C=C4)C5=C6C4=CC=CC6=C1C2=C35 VUFURXZETIQKNL-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 abstract 6
- 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 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- DHFMFICBVHCWGQ-UHFFFAOYSA-N (1-trimethylsilylnaphthalen-2-yl) trifluoromethanesulfonate Chemical compound C1=CC=C2C([Si](C)(C)C)=C(OS(=O)(=O)C(F)(F)F)C=CC2=C1 DHFMFICBVHCWGQ-UHFFFAOYSA-N 0.000 abstract 1
- XBHPFCIWRHJDCP-UHFFFAOYSA-N (2-trimethylsilylphenyl) trifluoromethanesulfonate Chemical compound C[Si](C)(C)C1=CC=CC=C1OS(=O)(=O)C(F)(F)F XBHPFCIWRHJDCP-UHFFFAOYSA-N 0.000 abstract 1
- OSZYFPWWHQEAGW-UHFFFAOYSA-N (3-trimethylsilylnaphthalen-2-yl) trifluoromethanesulfonate Chemical compound C1=CC=C2C=C(OS(=O)(=O)C(F)(F)F)C([Si](C)(C)C)=CC2=C1 OSZYFPWWHQEAGW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000006352 cycloaddition reaction Methods 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 1
- 238000000859 sublimation Methods 0.000 abstract 1
- 230000008022 sublimation Effects 0.000 abstract 1
- 238000005092 sublimation method Methods 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 sposób otrzymywania nafto-, lub antraceno- lub fenantro[1,2,3,4-ghi]perylenu, przedstawionych odpowiednio wzorami 1, 2 i 3, stanowiących π-rozszerzone pochodne perylenu, polegający na tym, że do reaktora wprowadza się perylen, mieszaninę stopionego sukcynonitrylu z 1,2-dimetoksyetanem w stosunku objętościowym od 3:1 do 1:3, w ilości od 5 do 50 ml na 1 mmol perylenu, oraz reagent generujący aryn w postaci fluorku cezu w ilości od 2 do 8 mmoli na 1 mmol perylenu, a następnie dodaje się prekursor arynu w postaci triflatu 2-trimetylosililofenylu lub triflatu 1-trimetylosililo-2-naftylu lub triflatu 3-trimetylosililo-2-naftylu, w ilości od 2 do 8 mmoli na 1 mmol perylenu, z szybkością nie większą niż 20 mmoli na minutę, dalej zawartość reaktora miesza się w temperaturze od 30°C do 80°C, w atmosferze gazu obojętnego, przez co najmniej dwie godziny. Korzystnie, po zakończeniu reakcji cykloaddycji, chłodzi się zawartość reaktora do temperatury nie wyższej niż 50°C, następnie odparowuje się lotne frakcje, pozostałość przemywa kilka razy niskowrzącym ciekłym nasyconym węglowodorem, następnie kilka razy wodą, po czym suszy przemyty osad w dowolny sposób, a pozostałość poddaje procesowi sublimacji pod ciśnieniem poniżej 1 mmHg, usuwając w ten sposób nieprzereagowany perylen, zaś surowe produkty pozostałe po sublimacji przemywa się kilkukrotnie niskowrzącym eterem, otrzymując oczyszczone produkty końcowe, w postaci nafto- lub antraceno- lub fenantro[1,2,3,4-ghi]perylenu o czystości większej niż 97% i wydajności do 95%.The subject of the invention is a method for obtaining naphtho- or anthracene- or phenanthro[1,2,3,4-ghi] perylene, represented by formulas 1, 2 and 3, respectively, which are π-expanded derivatives of perylene, consisting in introducing into the reactor perylene, a mixture of molten succinitrile with 1,2-dimethoxyethane in a volume ratio of 3:1 to 1:3, in an amount of 5 to 50 ml per 1 mmol of perylene, and a reagent generating arynes in the form of cesium fluoride in an amount of 2 to 8 mmol per 1 mmol of perylene, and then an aryne precursor in the form of 2-trimethylsilylphenyl triflate or 1-trimethylsilyl-2-naphthyl triflate or 3-trimethylsilyl-2-naphthyl triflate is added, in an amount of 2 to 8 mmol per 1 mmol of perylene, with at a rate of not more than 20 mmol per minute, the reactor contents are then stirred at a temperature of 30°C to 80°C, under an inert gas atmosphere, for at least two hours. Preferably, after completing the cycloaddition reaction, the contents of the reactor are cooled to a temperature not higher than 50°C, then the volatile fractions are evaporated, the residue is washed several times with a low-boiling liquid saturated hydrocarbon, then several times with water, and then the washed precipitate is dried in any way, and the residue is subjected to a sublimation process at a pressure below 1 mmHg, thus removing unreacted perylene, and the raw products remaining after sublimation are washed several times with low-boiling ether, obtaining purified final products in the form of naphtha-, anthracene- or phenanthro[1,2,3, 4-ghi]perylene with purity greater than 97% and yield up to 95%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL430592A PL238683B1 (en) | 2019-07-13 | 2019-07-13 | Method of naphtho-, anthraceno- and phenanthro[1,2,3,4-ghi]perylenes preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL430592A PL238683B1 (en) | 2019-07-13 | 2019-07-13 | Method of naphtho-, anthraceno- and phenanthro[1,2,3,4-ghi]perylenes preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL430592A1 true PL430592A1 (en) | 2021-01-25 |
| PL238683B1 PL238683B1 (en) | 2021-09-20 |
Family
ID=74222290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL430592A PL238683B1 (en) | 2019-07-13 | 2019-07-13 | Method of naphtho-, anthraceno- and phenanthro[1,2,3,4-ghi]perylenes preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL238683B1 (en) |
-
2019
- 2019-07-13 PL PL430592A patent/PL238683B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL238683B1 (en) | 2021-09-20 |
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