Reaction #2507810

Reaction equation

diisopropyl azodicarboxylate

Pentacene maleimide

Pentacene Maleimide

triphenyl phosphine

11-bromo-1-undecanol

→

5d

N-(11-bromoundecyl) maleimide pentacene

11-bromoundecylmaleimide pentacene

Solvents

THF

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONAfter completion of the addition
2. 2
   OtherThe solvent is evaporated under reduced pressure
3. 3
   Filtrationthe precipitate is filtered
4. 4
   Washwashed with 1:1 ether-hexane
5. 5
   Otherdried
6. 6
   OtherCrystallization from benzene

Procedure

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.

Source