PL447556A1 - Racemic 1-2;5-6-dibenzo-8,11-cis-dihydro-8,11-[1',2'-bis[di(4-tert-butylphenyl)amino]phenyl]ethene-1',2'-diyl]-N,N'-(2-ethylhexyl)perylenediimide and method of its preparation - Google Patents

Racemic 1-2;5-6-dibenzo-8,11-cis-dihydro-8,11-[1',2'-bis[di(4-tert-butylphenyl)amino]phenyl]ethene-1',2'-diyl]-N,N'-(2-ethylhexyl)perylenediimide and method of its preparation

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Publication number
PL447556A1
PL447556A1 PL447556A PL44755624A PL447556A1 PL 447556 A1 PL447556 A1 PL 447556A1 PL 447556 A PL447556 A PL 447556A PL 44755624 A PL44755624 A PL 44755624A PL 447556 A1 PL447556 A1 PL 447556A1
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PL
Poland
Prior art keywords
bis
butylphenyl
ethylhexyl
cis
tert
Prior art date
Application number
PL447556A
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Polish (pl)
Other versions
PL248634B1 (en
Inventor
Stanisław Krompiec
Milena Jarosz
Krzysztof Zemlak
Bartłomiej Kula
Piotr Lodowski
Patrycja Filipek
Karol Erfurt
Piotr Latos
Original Assignee
Uniwersytet Śląski W Katowicach
Politechnika Śląska
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Application filed by Uniwersytet Śląski W Katowicach, Politechnika Śląska filed Critical Uniwersytet Śląski W Katowicach
Priority to PL447556A priority Critical patent/PL248634B1/en
Publication of PL447556A1 publication Critical patent/PL447556A1/en
Publication of PL248634B1 publication Critical patent/PL248634B1/en

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    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Przedmiotem zgłoszenia jest racemiczny 1-2;5-6-dibenzo-8,11-cis-dihydro-8,11-[1',2'-bis[di(4-tert-butylofenylo)amino]fenylo]eten-1',2'-diylo]-N,N'-(2-etyloheksylo)perylenodiimidu, przedstawiony wzorem 1, stanowiący pi-rozszerzoną pochodną perylenodiimidu oraz sposób jego otrzymywania polegający na tym, że przeprowadza się proces cykloaddycji 1,2-bis{4-[di(4-tert-butylofenylo)amino]fenylo} acetylen do wnęki N,N'-bis(2-etyloheksylo)-cis-dibenzoperylenodiimidu, w taki sposób, że do reaktora wprowadza się w dowolnej kolejności: - N,N'-bis(2-etyloheksylo)-cis-dibenzoperylenodiimid, -1,2-bis{4-[di(4-tert-butylofenylo)amino]fenylo}acetylen oraz - topnik-rozpuszczalnik, w postaci eteru diarylowego, w proporcjach molowych reagentów: N,N'-bis(2-etyloheksylo)-cis-dibenzoperylenodiimid : 1,2-bis{4-[di(4-tert-butylofenylo)amino]fenylo}acetylen : topnik-rozpuszczalnik od 1:1:1 do 1:10:20, następnie w reaktorze wytwarza się próżnię, po czym w zamkniętym reaktorze miesza się jego zawartość, a jednocześnie podgrzewa się do temperatury z przedziału od 150°C do 180°C, homogenizuje mieszaninę reakcyjną, a dalej w zamkniętym reaktorze prowadzi się reakcję cykloaddycji w temperaturze od 180°C do 260°C, przez czas od 1 do 120 godzin, następnie reaktor wraz z mieszaniną poreakcyjną ochładza się do temperatury z przedziału od zera do 60°C, po czym mieszaninę poreakcyjną rozpuszcza się w niskowrzącym, dichloro- lub trichloroalkanie lub ich mieszaninie, a produkt cykloaddycji to jest racemiczny 1-2;5-6-dibenzo-8,11-cis-dihydro-8,11-[1',2'-bis[di(4-tert-butylofenylo)amino]fenylo]eten-1',2'-diylo]-N,N'-(2-etyloheksylo)perylenodiimidu wydziela się z mieszaniny poreakcyjnej, chromatograficznie na żelu krzemionkowym, eluując wpierw topnik-rozpuszczalnik, dalej nieprzereagowany dienofil, tj. 1,2-bis {4-[di(4-tert-butylofenylo)amino]fenylo}acetylen, nieprzereagowany N,N'-bis(2-etyloheksylo)-cis-dibenzoperylenodiimid i finalnie surowy produkt, wszystko za pomocą mieszaniny niskowrzącego, di- lub trichlorowanego węglowodoru nasyconego z niskowrzącym alkanem, cykloalkanem lub ich mieszaniną. Finalnie cykloaddukt otrzymuje się z wydajnością do 35%, o czystości do >98%.The subject of the application is racemic 1-2;5-6-dibenzo-8,11-cis-dihydro-8,11-[1',2'-bis[di(4-tert-butylphenyl)amino]phenyl]ethene-1',2'-diyl]-N,N'-(2-ethylhexyl)perylene diimide, represented by formula 1, which is a pi-extended derivative of perylene diimide, and a method for obtaining it, which consists in carrying out a cycloaddition process of 1,2-bis{4-[di(4-tert-butylphenyl)amino]phenyl}acetylene to the N,N'-bis(2-ethylhexyl)-cis-dibenzoperylene diimide cavity in such a way that the following are introduced into the reactor in any order: N,N'-bis(2-ethylhexyl)-cis-dibenzoperylenediimide, -1,2-bis{4-[di(4-tert-butylphenyl)amino]phenyl}acetylene and - flux-solvent, in the form of a diaryl ether, in the molar proportions of the reagents: N,N'-bis(2-ethylhexyl)-cis-dibenzoperylenediimide : 1,2-bis{4-[di(4-tert-butylphenyl)amino]phenyl}acetylene : flux-solvent from 1:1:1 to 1:10:20, then a vacuum is created in the reactor, after which its contents are mixed in a closed reactor and at the same time heated to a temperature in the range of 150°C to 180°C, the reaction mixture is homogenized, and then the cycloaddition reaction is carried out in the closed reactor at a temperature from 180°C to 260°C, for a time of 1 to 120 hours, then the reactor together with the post-reaction mixture is cooled to a temperature in the range from zero to 60°C, then the post-reaction mixture is dissolved in low-boiling dichloro- or trichloroalkane or their mixture, and the cycloaddition product, i.e. racemic 1-2;5-6-dibenzo-8,11-cis-dihydro-8,11-[1',2'-bis[di(4-tert-butylphenyl)amino]phenyl]ethene-1',2'-diyl]-N,N'-(2-ethylhexyl)perylene diimide is separated from the post-reaction mixture by chromatography on silica gel, eluting first the flux-solvent, then the unreacted dienophile, i.e. 1,2-bis {4-[di(4-tert-butylphenyl)amino]phenyl}acetylene, unreacted N,N'-bis(2-ethylhexyl)-cis-dibenzoperylenediimide, and finally the crude product, all by means of a mixture of a low-boiling, di- or trichlorinated saturated hydrocarbon with a low-boiling alkane, cycloalkane, or a mixture thereof. The final cycloadduct is obtained in yields up to 35% and purity up to >98%.

PL447556A 2024-01-20 2024-01-20 Racemic 1-2;5-6-dibenzo-8,11-cis-dihydro-8,11-[1',2'-bis[di(4-tert-butylphenyl)amino]phenyl]ethene-1',2'-diyl]-N,N'-(2-ethylhexyl)perylenediimide and method for obtaining it PL248634B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL447556A PL248634B1 (en) 2024-01-20 2024-01-20 Racemic 1-2;5-6-dibenzo-8,11-cis-dihydro-8,11-[1',2'-bis[di(4-tert-butylphenyl)amino]phenyl]ethene-1',2'-diyl]-N,N'-(2-ethylhexyl)perylenediimide and method for obtaining it

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Application Number Priority Date Filing Date Title
PL447556A PL248634B1 (en) 2024-01-20 2024-01-20 Racemic 1-2;5-6-dibenzo-8,11-cis-dihydro-8,11-[1',2'-bis[di(4-tert-butylphenyl)amino]phenyl]ethene-1',2'-diyl]-N,N'-(2-ethylhexyl)perylenediimide and method for obtaining it

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PL447556A1 true PL447556A1 (en) 2025-07-21
PL248634B1 PL248634B1 (en) 2026-01-05

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL441531A1 (en) * 2022-06-23 2023-12-27 Uniwersytet Śląski W Katowicach 2,3-bis(4-(N,N-di(4-tert-butylphenyl)amino)phenyl)-N,N'-bis(2 ethylhexyl)benzo[ghi]perylenediimide and method of its obtaining

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL441531A1 (en) * 2022-06-23 2023-12-27 Uniwersytet Śląski W Katowicach 2,3-bis(4-(N,N-di(4-tert-butylphenyl)amino)phenyl)-N,N'-bis(2 ethylhexyl)benzo[ghi]perylenediimide and method of its obtaining

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ANETA KURPANIK I IN.: "Chemistry – A European Journal 2020, 21, 12150-12157", „APEX STRATEGY REPRESENTED BY DIELS-ALDER CYCLOADDITIONS – NEW OPPORTUNITIES FOR THE SYNTHESES OF FUNCTIONALISED PAHS" *
ANETA KURPANIK I IN.: "Molecules 2020, 25, 5373", „DIELS-ALDER CYCLOADDITION TO THE BAY REGION OF PERYLENE AND ITS DERIVATIVES AS AN ATTRACTIVE STRATEGY FOR PAH CORE EXPANSION: THEORETICAL AND PRACTICAL ASPECTS" *

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