Reaktion #2421

Reaktionsgleichung

N,N'-diphenyl-1,4-phenylenediamine

4-iodochlorobenzene

18-crown-6 ether

potassium carbonate

1,2-dichlorobenzene

→

grey-white solid

N,N'-diphenyl-N,N'-di-(4-chlorophenyl)-1,4-phenylenediamine

Lösungsmittel

hexane

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 1 L, three-necked, round-bottomed flask, equipped with an overhead stirrer, a nitrogen inlet and a reflux condenser
2. 2
   SonstigeWith a slow purge of nitrogen through the condenser
3. 3
   Sonstigethe reaction vessel was placed in an oil bath
4. 4
   Sonstigethe stirred reaction
5. 5
   FiltrationThe hot reaction mixture was filtered through a bed
6. 6
   Filtrationof filtering aid, which
7. 7
   Waschenwas washed with toluene (50 mL)
8. 8
   Einengenthe filtrate was concentrated on a rotavapor under reduced pressure
9. 9
   SonstigeThe solvent residue was further removed with a Kugelrohr apparatus
10. 10
    Sonstigeto afford a dark brown viscous oil

Vorschrift

A 1 L, three-necked, round-bottomed flask, equipped with an overhead stirrer, a nitrogen inlet and a reflux condenser, was charged with N,N'-diphenyl-1,4-phenylenediamine (13.0 g, 0.05 mol), 4-iodochlorobenzene (31.0 g, 0.13 mol), copper bronze powder (12.7 g, 0.20 mol), 18-crown-6 ether (2.6 g, 0.10 mol), powdered potassium carbonate (50.1 g. 0.36 mol) and 1,2-dichlorobenzene (120 mL). With a slow purge of nitrogen through the condenser, the reaction vessel was placed in an oil bath and the stirred reaction was heated at 200° C. for 20 hours. The hot reaction mixture was filtered through a bed of filtering aid, which was washed with toluene (50 mL), and the filtrate was concentrated on a rotavapor under reduced pressure. The solvent residue was further removed with a Kugelrohr apparatus to afford a dark brown viscous oil. Flash chromatography on a silica gel column (5×25 cm, 5% CH2Cl2 in hexane as eluent) afforded 9.6 g of grey-white solid. The crude product was further washed with toluene and acetone to provide 6.1 g (25%) of off-white powdered material. The polymer of this example is useful for hole transport materials in light-emitting diode devices.

Quelle