PL431010A1 - Method of preparing 1,2-diarylbenzo[ghi]perylenes - Google Patents
Method of preparing 1,2-diarylbenzo[ghi]perylenesInfo
- Publication number
- PL431010A1 PL431010A1 PL431010A PL43101019A PL431010A1 PL 431010 A1 PL431010 A1 PL 431010A1 PL 431010 A PL431010 A PL 431010A PL 43101019 A PL43101019 A PL 43101019A PL 431010 A1 PL431010 A1 PL 431010A1
- Authority
- PL
- Poland
- Prior art keywords
- perylene
- saturated
- diarylbenzo
- cycloaddition
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 150000002979 perylenes Chemical class 0.000 title 1
- -1 phenyl 9,9-dibutylfluoren-2-yl Chemical group 0.000 abstract 6
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- 150000002430 hydrocarbons Chemical class 0.000 abstract 4
- 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 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- 238000006352 cycloaddition reaction Methods 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000011555 saturated liquid Substances 0.000 abstract 2
- 239000000758 substrate Substances 0.000 abstract 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 206010020772 Hypertension Diseases 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 239000002086 nanomaterial Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 238000000859 sublimation Methods 0.000 abstract 1
- 230000008022 sublimation Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000002061 vacuum sublimation Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem wynalazku jest sposób otrzymywania 1,2-diarylobenzo[ghi]perylenów o wzorze ogólnym 1, polegający na tym, że przeprowadza się proces cykloaddycji wybranego 1,2-diaryloacetylenu do wnęki perylenu z równoczesną eliminacją wodoru, w taki sposób, że do reaktora odpornego na nadciśnienie, wprowadza się - w dowolnej kolejności - perylen oraz 1,2-diaryloacetylen, w którym grupę arylową stanowi aryl wybrany spośród: fenyl 9,9-dibutylofluoren-2-yl, 9,9-dioktylofluoren-2-yl, N-oktylokarbazol-3-yl, p-tert-butylofenyl, 4-(N,N-di(4-tert-butylofenylo)amino))fenyl, 1-naftyl, N-(2-etyloheksylo)ftaloimid-4-yl, w proporcjach molowych od 1,5:1 do 20:1, następnie reaktor zamyka się i wytwarza w nim próżnię, to jest ciśnienie o wartości nie wyższej niż 0,1 Pa, usuwając praktycznie tlen i lotne substancje, na przykład rozpuszczalniki, po czym prowadzi się reakcję w temperaturze od 250 do 300°C, przez czas nie krótszy niż 12 godzin, a po zakończeniu reakcji cykloaddycji 1,2-diarylobenzo[ghi]perylen wydziela się dwuetapowo: nadmiarowy perylen usuwa się na drodze próżniowej sublimacji w znany sposób, a z pozostałości po sublimacji izoluje się produkty chromatograficznie, na kolumnie z żelem krzemionkowym, przy czym najpierw eluuje się pozostałości nieprzereagowanych substratów i niektóre zanieczyszczenia za pomocą niskowrzącego, nasyconego, ciekłego węglowodoru lub mieszaniny ciekłych węglowodorów nasyconych, korzystnie za pomocą pentanu lub heksanu, po czym finalnie produkt końcowy eluuje się za pomocą niskowrzącego, nasyconego, ciekłego węglowodoru lub mieszaniny ciekłych węglowodorów nasyconych, zmieszanych z dichlorometanem lub chloroformem w proporcjach objętościowych rozpuszczalnik węglowodorowy/rozpuszczalnik chlorowany od 1:10 do 50:1. Produkty reakcji mogą być luminoforami, prekursorami nanografenów lub nanomateriałów dla organicznej elektroniki lub substratami dla dalszych cykloaddycji lub cyklo-dehydrokondensacji.The subject of the invention is a process for the preparation of 1,2-diarylbenzo [gh] perylene of the general formula 1, consisting in carrying out the cycloaddition process of selected 1,2-diaryl acetylene into the perylene cavity with simultaneous elimination of hydrogen, in such a way that the resistant reactor is for hypertension, introduce - in any order - perylene and 1,2-diaryl acetylene, in which the aryl group is an aryl selected from: phenyl 9,9-dibutylfluoren-2-yl, 9,9-dioctylfluoren-2-yl, N- octylcarbazol-3-yl, p-tert-butylphenyl, 4- (N, N-di (4-tert-butylphenyl) amino)) phenyl, 1-naphthyl, N- (2-ethylhexyl) phthalimid-4-yl, in in molar proportions from 1.5: 1 to 20: 1, then the reactor is closed and a vacuum is created in it, i.e. a pressure of not more than 0.1 Pa, practically removing oxygen and volatile substances, for example solvents, and then carrying out the reaction is carried out at a temperature of 250 to 300 ° C for a period of not less than 12 hours, and after the completion of the 1,2-diarylbenzo [gh] perils cycloaddition reaction n is separated in two stages: the excess perylene is removed by vacuum sublimation in a known manner, and the products after sublimation are isolated by chromatography on a silica gel column, first eluting the residues of unreacted substrates and some impurities with low-boiling, saturated, liquid hydrocarbon or a mixture of saturated liquid hydrocarbons, preferably with pentane or hexane, then finally the final product is eluted with a low-boiling saturated liquid hydrocarbon or a mixture of liquid saturated hydrocarbons mixed with dichloromethane or chloroform in the proportions by volume hydrocarbon solvent / chlorinated solvent from 1 : 10 to 50: 1. The reaction products can be phosphors, nanographs or nanomaterials precursors for organic electronics, or substrates for further cycloaddition or cyclo-dehydrocondensation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL431010A PL238586B1 (en) | 2019-08-30 | 2019-08-30 | Method for the preparation of 1,2-diarylbenzo [gh] perylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL431010A PL238586B1 (en) | 2019-08-30 | 2019-08-30 | Method for the preparation of 1,2-diarylbenzo [gh] perylene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL431010A1 true PL431010A1 (en) | 2021-03-08 |
| PL238586B1 PL238586B1 (en) | 2021-09-13 |
Family
ID=75107755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL431010A PL238586B1 (en) | 2019-08-30 | 2019-08-30 | Method for the preparation of 1,2-diarylbenzo [gh] perylene |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL238586B1 (en) |
-
2019
- 2019-08-30 PL PL431010A patent/PL238586B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL238586B1 (en) | 2021-09-13 |
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