Toluene → 3,8-Bis(biphen-4-yl)fluoranthene

HRID 1725155

Reaktionsgleichung

Reaktionsgleichung von HRID 1725155
BrC1C=CC2[C:6]3[C:11]([C:12]4[C:17]=2[C:16]=1[CH:15]=[CH:14][CH:13]=4)=[CH:10][C:9](Br)=[CH:8][CH:7]=3.[CH:19]1[C:33]2=[C:34]3[C:26]([C:27]4[C:32]2=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][CH:24]=[CH:23][C:22]3=[CH:21][CH:20]=1.BrBr.[C:37]1([CH3:43])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)(Cl)Cl>[C:40]1([C:23]2[CH:24]=[CH:25][C:26]3[C:27]4[C:32]([C:33]5[C:34]=3[C:22]=2[CH:21]=[CH:20][CH:19]=5)=[CH:31][C:30]([C:15]2[CH:14]=[CH:13][C:12]([C:11]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:17][CH:16]=2)=[CH:29][CH:28]=4)[CH:41]=[CH:42][C:37]([C:43]2[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=2)=[CH:38][CH:39]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 9154FluorantheneHCID 24408BromineHCID 807833,8-Dibromofluoranthene

Produkt 1

HCID 575621093,8-Bis(biphen-4-yl)fluorantheneAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1 g of 3,8-dibromofluoranthene, prepared by dibromination of fluoranthene in chloroform with elemental bromine, was dissolved under protective gas in 100 ml of dried toluene and degassed repeatedly. 19.4 g of potassium carbonate dissolved in 47 ml of ethanol/water (1:1 parts by volume) and 1 g of 4-biphenylboronic acid were added and degassed again. Subsequently, 0.32 g of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) was added under protective gas and the mixture was stirred at 80° C. for 16 hours. The reaction mixture was filtered and dried. Yield: 14% as a yellowish solid. λmax,em (toluene)=479 nm, quantum yield (toluene): 74%.

Aufarbeitung

  1. customdegassed repeatedly
  2. dissolution19.4 g of potassium carbonate dissolved in 47 ml of ethanol/water (1:1 parts by volume)
  3. addition1 g of 4-biphenylboronic acid were added
  4. customdegassed again
  5. additionSubsequently, 0.32 g of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) was added under protective gas
  6. filtrationThe reaction mixture was filtered
  7. customdried
  8. customλmax,em (toluene)=479 nm, quantum yield (toluene)

Quellen und Nachweise

ORD-Eintrag
ord-d0c8c191593c4ec19f462db2062298cd
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07488856B2

Verknüpfte Notizen

Wird geladen…