PL441530A1 - 2,3-bis(9,9-dibutylfluoren-2-yl)-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of its obtaining - Google Patents
2,3-bis(9,9-dibutylfluoren-2-yl)-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of its obtainingInfo
- Publication number
- PL441530A1 PL441530A1 PL441530A PL44153022A PL441530A1 PL 441530 A1 PL441530 A1 PL 441530A1 PL 441530 A PL441530 A PL 441530A PL 44153022 A PL44153022 A PL 44153022A PL 441530 A1 PL441530 A1 PL 441530A1
- Authority
- PL
- Poland
- Prior art keywords
- bis
- ethylhexyl
- flux
- solvent
- dibutylfluoren
- 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 4
- -1 9,9-dibutylfluoren-2-yl Chemical group 0.000 title abstract 3
- 125000005605 benzo group Chemical group 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 239000002904 solvent Substances 0.000 abstract 4
- 238000006352 cycloaddition reaction Methods 0.000 abstract 3
- 150000001993 dienes Chemical class 0.000 abstract 3
- 239000000758 substrate Substances 0.000 abstract 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 2
- 238000004587 chromatography analysis Methods 0.000 abstract 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 150000001987 diarylethers Chemical class 0.000 abstract 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003480 eluent Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000002086 nanomaterial Substances 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
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/10—Cyclisation
- C07B37/12—Diels-Alder reactions
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem zgłoszenia jest 2,3-bis(9,9-dibutylofluoren-2-ylo)-N,N'-bis(2-etyloheksylo)benzo[ghi]perylenodiimid przedstawiony wzorem 1 oraz sposób jego otrzymywania pokazany na schemacie 1, polegający na tym, że do reaktora odpornego na nadciśnienie, korzystnie co najmniej do 2 atmosfer, wprowadza się w dowolnej kolejności: N,N'-bis(2-etyloheksylo)perylenodiimid będący dienem, -1,2-bis(9,9-dibutylofluoren-2-ylo)acetylen będący dienofilem, -topnik-rozpuszczalnik, w postaci eteru diarylowego, najkorzystniej eteru di-para-tolilowego lub di-fenylowego, w proporcjach molowych dien:dienofil od 10:1 do 1:10, zaś topnik-rozpuszczalnik od 1 do 10 moli na 1 mol użytego dienofila, w reaktorze wytwarza się próżnię, to jest ciśnienie o wartości nie wyższej niż 0,01 Pa, usuwając w ten sposób powietrze i lotne substancje, a reakcję prowadzi się w zamkniętym reaktorze w temperaturze od 260 do 300°C przez czas nie krótszy niż 48 godzin, a po zakończeniu reakcji cykloaddycji 2,3-bis(9,9-dibutylofluoren-2-ylo)-N,N'-bis(2-etyloheksylo)benzo[ghi]perylenodiimid wydziela się chromatograficznie na żelu krzemionkowym, eluując wpierw topnik-rozpuszczalnik, dalej nieprzereagowany substrat acetylenowy, następnie produkt i finalnie nieprzereagowany dien - wszystko za pomocą chlorowanego, niskowrzącego węglowodoru. Odzyskane w trakcie chromatografii substraty oraz topnik-rozpuszczalnik podlegają recyklingowi - mogą być użyte do kolejnych reakcji cykloaddycji. Recyklingowi podlega także eluent stosowany do chromatografii. Produkt reakcji może być luminoforem, prekursorem nanografenów lub nanomateriałów dla organicznej elektroniki, składnikiem warstw aktywnych, na przykład w diodach typu OLED lub substratem dla dalszych cykloaddycji lub cyklo-dehydrokondensacji.The subject of the application is 2,3-bis(9,9-dibutylfluoren-2-yl)-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide presented by formula 1 and the method of its preparation shown in scheme 1, consisting in in that the reactor resistant to overpressure, preferably to at least 2 atmospheres, is introduced in any order: N,N'-bis(2-ethylhexyl)perylene diimide, which is a diene, -1,2-bis(9,9-dibutylfluorene- 2-yl)acetylene being a dienophile, -flux-solvent, in the form of diaryl ether, most preferably di-para-tolyl or di-phenyl ether, in molar proportions of diene:dienophile from 10:1 to 1:10, and the flux-solvent from 1 to 10 moles per 1 mole of dienophile used, a vacuum is created in the reactor, i.e. a pressure of not more than 0.01 Pa, thus removing air and volatile substances, and the reaction is carried out in a closed reactor at a temperature of 260 to 300°C for not less than 48 hours, and after completing the cycloaddition reaction, 2,3-bis(9,9-dibutylfluoren-2-yl)-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide secretes chromatographically on silica gel, eluting first the flux-solvent, then the unreacted acetylene substrate, then the product and finally the unreacted diene - all using a chlorinated, low-boiling hydrocarbon. The substrates and flux-solvent recovered during chromatography are recycled - they can be used for subsequent cycloaddition reactions. The eluent used for chromatography is also recycled. The reaction product can be a phosphor, a precursor of nanographenes or nanomaterials for organic electronics, a component of active layers, for example in OLEDs, or a substrate for further cycloadditions or cyclo-dehydrocondensations.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL441530A PL247454B1 (en) | 2022-06-23 | 2022-06-23 | 2,3-bis(9,9-dibutylfluoren-2-yl)-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of obtaining it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL441530A PL247454B1 (en) | 2022-06-23 | 2022-06-23 | 2,3-bis(9,9-dibutylfluoren-2-yl)-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of obtaining it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL441530A1 true PL441530A1 (en) | 2023-12-27 |
| PL247454B1 PL247454B1 (en) | 2025-07-07 |
Family
ID=89452893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL441530A PL247454B1 (en) | 2022-06-23 | 2022-06-23 | 2,3-bis(9,9-dibutylfluoren-2-yl)-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and method of obtaining it |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL247454B1 (en) |
-
2022
- 2022-06-23 PL PL441530A patent/PL247454B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL247454B1 (en) | 2025-07-07 |
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