Pentacene → Pentacene maleimide

HRID 1359897

Reaktionsgleichung

Reaktionsgleichung von HRID 1359897
[CH:1]1[C:22]2[C:5](=[CH:6][C:7]3[C:20]([CH:21]=2)=[CH:19][C:18]2[C:9](=[CH:10][C:11]4[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[C:23]1(=[O:29])[NH:27][C:26](=[O:28])[CH:25]=[CH:24]1>C1C(Cl)=CC=C(Cl)C=1>[CH:4]1[C:5]2[C:22](=[CH:21][C:20]3[C:7]([CH:6]=2)=[CH:8][C:9]2[C:18](=[CH:17][C:16]4[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:19]=3)[CH:1]=[CH:2][CH:3]=1.[C:26]1(=[O:28])[NH:27][C:23](=[O:29])[CH:24]=[CH:25]1

Komponenten

4

Edukt 2

HCID 8671PentaceneHCID 10935Maleimide

Produkt 1

HCID 86643198Pentacene maleimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 46851,4-DichlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A suspension of pentacene (287 mg, 1 mmole) and maleimide (1 mmole) in 4 mL of dichlorobenzene is heated to 160° C. for 4 hours. The mixture is cooled to room temperature and the precipitate is filtered, washed with toluene and dried. Recrystallization from dichlorobenzene affords pure samples of pentacene-maleimide adduct as white needles. N-(11-bromoundecyl) maleimide-pentacene adduct (5d): Pentacene-maleimide adduct (5c) (375 mg, 1 mmole) are added to a solution of triphenyl phosphine (393 mg. 1.5 mmole) and 11-bromo-1-undecanol (375 mg, 1.5 mmole) in 40 mL of anhydrous tetrahydrofuran. To this mixture a solution of diisopropyl azodicarboxylate (300 mg, 1.5 mmole) in 10 mL of anhydrous THF is added dropwise under a stream of nitrogen. After completion of the addition, the solution is stirred at room temperature for 18 hours. The solvent is evaporated under reduced pressure and the residue is titrated with diethyl ether and the precipitate is filtered, washed with 1:1 ether-hexane and dried. Crystallization from benzene affords the pure sample of 11-bromoundecylmaleimide-pentacene adduct 5d.

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationthe precipitate is filtered
  3. washwashed with toluene
  4. customdried
  5. customRecrystallization from dichlorobenzene

Quellen und Nachweise

ORD-Eintrag
ord-e8304dbf10f14e2eae7256474439bdc5
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879307B2

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