PL442236A1 - 3,4-bis(4-bromophenyl)-7,14-bis(2,4,6-trimethylphenyl)dibenzo[bc,ef]coronene and method of its preparation - Google Patents

3,4-bis(4-bromophenyl)-7,14-bis(2,4,6-trimethylphenyl)dibenzo[bc,ef]coronene and method of its preparation

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Publication number
PL442236A1
PL442236A1 PL442236A PL44223622A PL442236A1 PL 442236 A1 PL442236 A1 PL 442236A1 PL 442236 A PL442236 A PL 442236A PL 44223622 A PL44223622 A PL 44223622A PL 442236 A1 PL442236 A1 PL 442236A1
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PL
Poland
Prior art keywords
mixture
bis
boiling
low
product
Prior art date
Application number
PL442236A
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Polish (pl)
Other versions
PL245648B1 (en
Inventor
Stanisław Krompiec
Angelika Mieszczanin
Marek Matussek
Aleksandra Fijołek
Szymon Rogalski
Cezary Pietraszuk
Karol Erfurt
Original Assignee
Uniwersytet Śląski W Katowicach
Uniwersytet Im. Adama Mickiewicza W Poznaniu
Politechnika Śląska
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Application filed by Uniwersytet Śląski W Katowicach, Uniwersytet Im. Adama Mickiewicza W Poznaniu, Politechnika Śląska filed Critical Uniwersytet Śląski W Katowicach
Priority to PL442236A priority Critical patent/PL245648B1/en
Publication of PL442236A1 publication Critical patent/PL442236A1/en
Publication of PL245648B1 publication Critical patent/PL245648B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/30—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by a Diels-Alder synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems

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

Abstract

Istotę zgłoszenia stanowi 3,4-bis(4-bromofenylo)-7,14-bis(2,4,6-trimetylofenylo)dibenzo[bc,ef]koronen przedstawiony wzorem 1, oraz sposób jego otrzymywania polegający na tym, że do reaktora wprowadza się 7,14-di-mezytylo-bisanten, dienofil w postaci 1,2-bis(p-bromofenylo)acetylenu oraz topnik w postaci trwałego do temperatury co najmniej 280°C eteru diarylowego, w proporcjach molowych od 1:1:1 do 1:20:40, następnie poprzez wytworzenie w reaktorze próżni usuwa się z mieszaniny i przestrzeni reakcyjnej tlen i lotne substancje, następnie w zamkniętym reaktorze ogrzewa się mieszaninę reakcyjną w temperaturze od 200°C do 260°C, przez co najmniej 1 godzinę, a po zakończeniu reakcji cykloaddycji produkt, to jest 3,4-bis(4-bromofenylo)-7,14-bis(2,4,6-trimetylofenylo)dibenzo[bc,ef]koronen wydziela się dwuetapowo, wpierw usuwa się topnik oraz nadmiarowy dienofil na drodze chromatografii kolumnowej na żelu krzemionkowym, za pomocą mieszaniny niskowrzącego węglowodoru lub mieszaniny takich niskowrzących węglowodorów z niskowrzącym, chlorowanym, nasyconym węglowodorem lub z mieszaniną takich niskowrzących, chlorowanych, nasyconych węglowodorów, w proporcjach objętościowych od 100:1 do 1:10, a następnie, kontynuując elucję izoluje się produkt chromatograficznie, na tej samej kolumnie za pomocą mieszaniny niskowrzącego, chlorowanego, nasyconego węglowodoru lub mieszaniny takich niskowrzących chlorowanych, nasyconych węglowodorów, z niskowrzącym węglowodorem lub z mieszaniną takich węglowodorów, w proporcjach objętościowych od 10:1 do 1:10. Surowy produkt korzystnie poddaje się finalnemu oczyszczaniu celem uzyskania produktu o czystości większej niż 98%. Produkt może być luminoforem, prekursorem nanografenów lub nanomateriałów dla organicznej elektroniki i fotowoltaiki, w tym materiałów transportujących dziury lub substratem do dalszych funkcjonalizacji, w tym sprzęgania, aminowania, cykloaddycji lub cyklo-dehydrokondensacji.The essence of the application is 3,4-bis(4-bromophenyl)-7,14-bis(2,4,6-trimethylphenyl)dibenzo[bc,ef]coronene presented by formula 1, and the method of its preparation consisting in 7,14-di-mesityl-bisanthene, a dienophile in the form of 1,2-bis(p-bromophenyl)acetylene and a flux in the form of diaryl ether stable to a temperature of at least 280°C are introduced, in molar proportions from 1:1:1 to 1:20:40, then by creating a vacuum in the reactor, oxygen and volatile substances are removed from the mixture and the reaction space, then the reaction mixture is heated in a closed reactor at a temperature from 200°C to 260°C for at least 1 hour, and after completing the cycloaddition reaction, the product, i.e. 3,4-bis(4-bromophenyl)-7,14-bis(2,4,6-trimethylphenyl)dibenzo[bc,ef]coronene, is isolated in two stages, first the flux is removed and excess dienophile by silica gel column chromatography with a mixture of a low-boiling hydrocarbon or a mixture of such low-boiling hydrocarbons with a low-boiling, chlorinated, saturated hydrocarbon or with a mixture of such low-boiling, chlorinated, saturated hydrocarbons in volume proportions from 100:1 to 1:10, and then, continuing elution, the product is isolated chromatographically on the same column using a mixture of a low-boiling, chlorinated, saturated hydrocarbon or a mixture of such low-boiling, chlorinated, saturated hydrocarbons, with a low-boiling hydrocarbon or with a mixture of such hydrocarbons, in volume proportions from 10:1 to 1 :10. The raw product is preferably subjected to final purification to obtain a product with a purity greater than 98%. The product can be a phosphor, a precursor of nanographenes or nanomaterials for organic electronics and photovoltaics, including hole transport materials, or a substrate for further functionalizations, including coupling, amination, cycloaddition or cyclo-dehydrocondensation.

PL442236A 2022-09-11 2022-09-11 3,4-bis(4-bromophenyl)-7,14-bis(2,4,6-trimethylphenyl)dibenzo[bc,ef]coronene and method of its preparation PL245648B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL442236A PL245648B1 (en) 2022-09-11 2022-09-11 3,4-bis(4-bromophenyl)-7,14-bis(2,4,6-trimethylphenyl)dibenzo[bc,ef]coronene and method of its preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL442236A PL245648B1 (en) 2022-09-11 2022-09-11 3,4-bis(4-bromophenyl)-7,14-bis(2,4,6-trimethylphenyl)dibenzo[bc,ef]coronene and method of its preparation

Publications (2)

Publication Number Publication Date
PL442236A1 true PL442236A1 (en) 2024-03-18
PL245648B1 PL245648B1 (en) 2024-09-09

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PL442236A PL245648B1 (en) 2022-09-11 2022-09-11 3,4-bis(4-bromophenyl)-7,14-bis(2,4,6-trimethylphenyl)dibenzo[bc,ef]coronene and method of its preparation

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PL (1) PL245648B1 (en)

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Publication number Publication date
PL245648B1 (en) 2024-09-09

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