PL433408A1 - 2,3-diphenyl-N,N'-bis(2,6-diisopropylphenyl)benzo[ghi]perylenediimide and method of its preparation - Google Patents
2,3-diphenyl-N,N'-bis(2,6-diisopropylphenyl)benzo[ghi]perylenediimide and method of its preparationInfo
- Publication number
- PL433408A1 PL433408A1 PL433408A PL43340820A PL433408A1 PL 433408 A1 PL433408 A1 PL 433408A1 PL 433408 A PL433408 A PL 433408A PL 43340820 A PL43340820 A PL 43340820A PL 433408 A1 PL433408 A1 PL 433408A1
- Authority
- PL
- Poland
- Prior art keywords
- diisopropylphenyl
- bis
- saturated
- benzo
- diphenyl
- Prior art date
Links
- 125000005605 benzo group Chemical group 0.000 title abstract 3
- KJOLVZJFMDVPGB-UHFFFAOYSA-N perylenediimide Chemical compound C=12C3=CC=C(C(NC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 KJOLVZJFMDVPGB-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 8
- 229930195733 hydrocarbon Natural products 0.000 abstract 8
- 150000002430 hydrocarbons Chemical class 0.000 abstract 8
- 239000004215 Carbon black (E152) Substances 0.000 abstract 5
- 239000011555 saturated liquid Substances 0.000 abstract 5
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 3
- 238000009835 boiling Methods 0.000 abstract 3
- 229910000071 diazene Inorganic materials 0.000 abstract 3
- 239000007788 liquid Substances 0.000 abstract 3
- -1 2,6-diisopropylphenyl Chemical group 0.000 abstract 2
- DYWJOZXDMINJGX-UHFFFAOYSA-N CC(C)C(C=CC=C1C(C)C)=C1C1=CC2=CC=C(C=CC=C34)C3=C2C2=C1C=CC1=CC=CC4=C21 Chemical group CC(C)C(C=CC=C1C(C)C)=C1C1=CC2=CC=C(C=CC=C34)C3=C2C2=C1C=CC1=CC=CC4=C21 DYWJOZXDMINJGX-UHFFFAOYSA-N 0.000 abstract 2
- 238000004587 chromatography analysis Methods 0.000 abstract 2
- 238000006352 cycloaddition reaction Methods 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- QASNXPHSCPXRGE-UHFFFAOYSA-N 1-[2,6-di(propan-2-yl)phenyl]perylene Chemical group CC(C)C1=CC=CC(C(C)C)=C1C1=CC=C(C=CC=C23)C2=C1C1=C2C3=CC=CC2=CC=C1 QASNXPHSCPXRGE-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000010790 dilution Methods 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- 238000010828 elution Methods 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 239000000499 gel Substances 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 239000002086 nanomaterial Substances 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 238000000859 sublimation Methods 0.000 abstract 1
- 230000008022 sublimation Effects 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 238000002061 vacuum sublimation Methods 0.000 abstract 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
Przedmiotem wynalazku jest 2,3-difenylo-N,N'-bis(2,6-diizopropylofenylo)benzo[ghi]perylenodiimid przedstawiony wzorem 1 oraz sposób jego otrzymywania polegający na tym, że do reaktora odpornego na nadciśnienie wprowadza się N,N'-bis(2,6-diizopropylofenylo)perylenodiimid oraz 1,2-difenyloacetylen w proporcjach molowych od 1:2 do 1:50, reaktor zamyka się i wytwarza w nim próżnię, po czym prowadzi się reakcję w temperaturze od 260 do 310°C, przez czas nie krótszy niż 24 godziny, a po zakończeniu reakcji cykloaddycji 2,3-difenylo-N,N'-bis(2,6-diizopropylofenylo)benzo[ghi]perylenodiimid wydziela się w dwojaki sposób, to jest albo: a) nadmiarowy 1,2-difenyloacetylen usuwa się za pomocą próżniowej sublimacji w znany sposób, a z pozostałości po sublimacji izoluje się produkt chromatograficznie, na kolumnie z żelem krzemionkowym, przy czym najpierw eluuje się pozostałości nieprzereagowanego difenyloacetylenu i niektóre zanieczyszczenia za pomocą niskowrzącego, nasyconego, ciekłego węglowodoru lub mieszaniny ciekłych węglowodorów nasyconych, a finalnie produkt, to jest 2,3-difenylo-N,N'-bis(2,6-diizopropylofenylo)benzo[ghi]perylenodiimid eluuje się za pomocą niskowrzącego, nasyconego, ciekłego węglowodoru zmieszanego z dichlorometanem lub chloroformem lub mieszaniny ciekłych węglowodorów nasyconych, zmieszanych z dichlorometanem lub chloroformem, w proporcjach objętościowych rozpuszczalnik węglowodorowy/rozpuszczalnik chlorowany od 1:1 do 1:100, albo: b) nadmiarowy 1,2-difenyloacetylen usuwa się eluując go chromatograficznie, na kolumnie z żelem krzemionkowym, ciekłym, nasyconym węglowodorem lub mieszaniną nasyconych, ciekłych węglowodorów, a finalnie produkt, to jest 2,3-difenylo-N,N'-bis(2,6-diizopropylofenylo)benzo[ghi]perylenodiimid eluuje się za pomocą niskowrzącego, nasyconego, ciekłego węglowodoru zmieszanego z dichlorometanem lub chloroformem lub mieszaniny ciekłych węglowodorów nasyconych, zmieszanych z dichlorometanem lub chloroformem, proporcjach objętościowych rozpuszczalnik węglowodorowy/rozpuszczalnik chlorowany od 1:1 do 1:100. Produkt reakcji może być luminoforem, prekursorem nanografenów lub nanomateriałów dla organicznej elektroniki, składnikiem warstw aktywnych, na przykład w OLED-ach lub substratem dla dalszych cykloaddycji lub cyklo-dehydrokondensacji.The subject of the invention is 2,3-diphenyl-N, N'-bis (2,6-diisopropylphenyl) benzo [gh] perylene diimide represented by the formula 1, and a method for its preparation consisting in introducing N, N 'into an overpressure-resistant reactor -bis (2,6-diisopropylphenyl) perylene diimide and 1,2-diphenylacetylene in molar proportions from 1: 2 to 1:50, the reactor is closed and a vacuum is created in it, and the reaction is carried out at a temperature of 260 to 310 ° C , for a time not shorter than 24 hours, and after the cycloaddition reaction is completed, 2,3-diphenyl-N, N'-bis (2,6-diisopropylphenyl) benzo [ghi] perylene diimide is isolated in two ways, that is either: a) the excess 1,2-diphenylacetylene is removed by vacuum sublimation in a known manner, and the product is isolated from the sublimation residue by chromatography on a silica gel column, first eluting unreacted diphenylacetylene residues and some impurities with a low-boiling, saturated liquid hydrocarbon NS or mixtures of saturated liquid hydrocarbons and finally the product, i.e. 2,3-diphenyl-N, N'-bis (2,6-diisopropylphenyl) benzo [gh] perylene diimide, is eluted with a low-boiling saturated liquid hydrocarbon mixed with dichloromethane or with chloroform or a mixture of saturated liquid hydrocarbons mixed with dichloromethane or chloroform, in the proportions by volume hydrocarbon solvent / chlorinated solvent from 1: 1 to 1: 100, or: b) the excess 1,2-diphenylacetylene is removed by chromatography elution on a gel column silica, liquid, saturated hydrocarbon or a mixture of saturated liquid hydrocarbons, and the final product, i.e. 2,3-diphenyl-N, N'-bis (2,6-diisopropylphenyl) benzo [ghi] perylene diimide, is eluted with low boiling, saturated , liquid hydrocarbon mixed with dichloromethane or chloroform, or a mixture of liquid saturated hydrocarbons mixed with dichloromethane or chloroform, the proportions by volume of dilution hydrocarbon solvent / chlorinated solvent from 1: 1 to 1: 100. The reaction product may be a phosphor, a nanografen or nanomaterials precursor for organic electronics, a component of active layers, for example in OLEDs, or a substrate for further cycloaddition or cyclo-dehydrocondensation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL433408A PL241965B1 (en) | 2020-03-31 | 2020-03-31 | 2,3-diphenyl-N,N'-bis(2,6-diisopropylphenyl)benzo[ghi]perylenediimide and method of its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL433408A PL241965B1 (en) | 2020-03-31 | 2020-03-31 | 2,3-diphenyl-N,N'-bis(2,6-diisopropylphenyl)benzo[ghi]perylenediimide and method of its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL433408A1 true PL433408A1 (en) | 2021-10-04 |
| PL241965B1 PL241965B1 (en) | 2023-01-02 |
Family
ID=78055936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL433408A PL241965B1 (en) | 2020-03-31 | 2020-03-31 | 2,3-diphenyl-N,N'-bis(2,6-diisopropylphenyl)benzo[ghi]perylenediimide and method of its preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL241965B1 (en) |
-
2020
- 2020-03-31 PL PL433408A patent/PL241965B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL241965B1 (en) | 2023-01-02 |
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