PL433403A1 - 2,3-diphenyl-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of its preparation - Google Patents
2,3-diphenyl-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of its preparationInfo
- Publication number
- PL433403A1 PL433403A1 PL433403A PL43340320A PL433403A1 PL 433403 A1 PL433403 A1 PL 433403A1 PL 433403 A PL433403 A PL 433403A PL 43340320 A PL43340320 A PL 43340320A PL 433403 A1 PL433403 A1 PL 433403A1
- Authority
- PL
- Poland
- Prior art keywords
- ethylhexyl
- bis
- benzo
- diphenyl
- diphenylacetylene
- Prior art date
Links
- 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 5
- 125000005605 benzo group Chemical group 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 6
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 abstract 5
- -1 2-ethylhexyl Chemical group 0.000 abstract 4
- 238000006352 cycloaddition reaction Methods 0.000 abstract 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- 238000004587 chromatography analysis Methods 0.000 abstract 2
- 229910000071 diazene Inorganic materials 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- 239000011555 saturated liquid Substances 0.000 abstract 2
- 239000000741 silica gel Substances 0.000 abstract 2
- 229910002027 silica gel Inorganic materials 0.000 abstract 2
- LQIRQSNFLPMJLT-UHFFFAOYSA-N C(C)C(CC1=CC=2C=3C4=C1C=CC1=CC=CC(C5=CC=CC(=CC=2)C=35)=C14)CCCC Chemical group C(C)C(CC1=CC=2C=3C4=C1C=CC1=CC=CC(C5=CC=CC(=CC=2)C=35)=C14)CCCC LQIRQSNFLPMJLT-UHFFFAOYSA-N 0.000 abstract 1
- PXXHQTTXAFOJNY-UHFFFAOYSA-N C(C)C(CC1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)CCCC Chemical group C(C)C(CC1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)CCCC PXXHQTTXAFOJNY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 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
- 239000002243 precursor Substances 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
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Przedmiotem wynalazku jest 2,3-difenylo-N,N'-bis(2-etyloheksylo)benzo[ghi]perylenodiimid przedstawiony wzorem 1 oraz sposób jego otrzymywania, który polega na tym, że przeprowadza się proces cykloaddycji 1,2-difenyloacetylenu do wnęki N,N'-bis(2-etyloheksylo)perylenodiimidu z równoczesną eliminacją wodoru, w taki sposób, że do reaktora odpornego na nadciśnienie, korzystnie co najmniej do 5 atmosfer, wprowadza się - w dowolnej kolejności - N,N'-bis(2-etyloheksylo)perylenodiimid oraz 1,2-difenyloacetylen w proporcjach molowych od 1:2 do 1:50, reaktor zamyka się i wytwarza w nim próżnię, to jest ciśnienie o wartości nie wyższej niż 0,1 Pa, usuwając praktycznie tlen i inne lotne substancje, 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-etyloheksylo)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-etyloheksylo)benzo[ghi]perylenodiimid eluuje się za pomocą dichlorometanu, albo: b) nadmiarowy 1,2-difenyloacetylen usuwa się eluując go chromatograficznie, na żelu krzemionkowym, ciekłym, nasyconym węglowodorem lub mieszaniną nasyconych, ciekłych węglowodorów, a finalnie produkt, to jest 2,3-difenylo-N,N'-bis(2-etyloheksylo)benzo[ghi]perylenodiimid eluuje się za pomocą dichlorometanu. 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-ethylhexyl) benzo [gh] perylenediimide represented by the formula 1 and a method for its preparation which consists in carrying out the process of cycloaddition of 1,2-diphenylacetylene into the cavity N, N'-bis (2-ethylhexyl) perylenediimide with simultaneous elimination of hydrogen, such that the overpressure-resistant reactor, preferably at least up to 5 atmospheres, is fed - in any order - N, N'-bis (2 -ethylhexyl) 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, i.e. a pressure of not more than 0.1 Pa, practically removing oxygen and other volatile substances, and then the reaction is carried out at a temperature from 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-ethylhexyl) benzo [ghi] perylene diimide is isolated in two ways, i.e. 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 the unreacted diphenylacetylene residues and some impurities with a low-boiling, saturated liquid hydrocarbon or a mixture of liquid saturated hydrocarbons, and finally the product, i.e. 2,3-diphenyl-N, N'-bis (2-ethylhexyl) benzo [gh] perylene diimide is eluted with dichloromethane, or: b) the excess 1,2-diphenylacetylene is removed by chromatography on silica gel, with a liquid, saturated hydrocarbon or a mixture of saturated liquid hydrocarbons, the final product, i.e. 2,3-diphenyl-N, N'-bis (2-ethylhexyl) benzo [gh] perylene diimide, is eluted with dichloromethane. 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 |
|---|---|---|---|
| PL433403A PL241962B1 (en) | 2020-03-31 | 2020-03-31 | 2,3-diphenyl-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL433403A PL241962B1 (en) | 2020-03-31 | 2020-03-31 | 2,3-diphenyl-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL433403A1 true PL433403A1 (en) | 2021-10-04 |
| PL241962B1 PL241962B1 (en) | 2023-01-02 |
Family
ID=78055910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL433403A PL241962B1 (en) | 2020-03-31 | 2020-03-31 | 2,3-diphenyl-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of its preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL241962B1 (en) |
-
2020
- 2020-03-31 PL PL433403A patent/PL241962B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL241962B1 (en) | 2023-01-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Amosova et al. | Addition of selenium dibromide to divinyl sulfide: Spontaneous rearrangement of 2, 6-dibromo-1, 4-thiaselenane to 5-bromo-2-bromomethyl-1, 3-thiaselenolane | |
| BRPI0516136A (en) | method and equipment for developing a group (iii) metal nitride film and group (iii) metal nitride film | |
| US20120181488A1 (en) | Method for the production of metal oxide-containing layers | |
| Hazarika et al. | Metal free synthesis of quinoxalines from alkynes via a cascade process using TsNBr2 | |
| Della Rosa et al. | Comparison of the reactivity between 2-and 3-nitropyrroles in cycloaddition reactions. A simple indole synthesis | |
| Trofimov et al. | Reactions of 2-phenylpyrrole with bromobenzoylacetylene on metal oxides active surfaces | |
| Winkler et al. | Gas-phase pyrolysis of heterocyclic compounds, part 1 and 2: flow pyrolysis and annulation reactions of some sulfur heterocycles: thiophene, benzo [b] thiophene, and dibenzothiophene. A product-oriented study | |
| Jiang et al. | Efficient ipso-nitration of arylboronic acids with iron nitrate as the nitro source | |
| PL441532A1 (en) | 2,3-bis(4-bromophenyl)-N,N'-bis(2-ethylhexyl)benzo[ghi]perylene diimide and method of its preparation | |
| PL433403A1 (en) | 2,3-diphenyl-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of its preparation | |
| Zeitter et al. | Pentacene to octacene: the limit of fourfold TIPS-ethynylation | |
| He et al. | Solubility and stability investigation of Titan aerosol analogs: New insight from NMR analysis | |
| Dai et al. | Distinct molecule adsorption behaviors on warped nanographene C80H30: A theoretical study | |
| Ender et al. | Mechanistic insights of seeded diamond growth from molecular precursors | |
| KR101586290B1 (en) | Method for reducing the aluminium content of neopentasilane | |
| Kuvychko et al. | Understanding polyarene trifluoromethylation with hot CF3 radicals using corannulene | |
| PL441530A1 (en) | 2,3-bis(9,9-dibutylfluoren-2-yl)-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of its obtaining | |
| KR102714372B1 (en) | Method for producing thin inorganic films | |
| PL433408A1 (en) | 2,3-diphenyl-N,N'-bis(2,6-diisopropylphenyl)benzo[ghi]perylenediimide and method of its preparation | |
| Xu et al. | Reactions of fluoroalkanesulfonyl azides with trimethylsilyl enol ethers | |
| PL442237A1 (en) | 1,2-bis(4-bromophenyl)benzo[ghi]perylene and method of its preparation | |
| PL433407A1 (en) | 2,3-bis[N-(2-ethylhexyl)phthalimido-4-yl]-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and its preparation | |
| KR20250087522A (en) | Silicon-containing film precursor, composition for forming silicon-containing film, method for producing sulfur-containing siloxane, and method for producing silicon-containing film | |
| Gerasov et al. | Reactions of t-Boc-Protected Amines with Difluorocarbene | |
| RU2015128392A (en) | METHOD FOR HYDROPHOBIZATION OF THE INTERNAL SURFACE OF THE SUBSTRATE |