Reaction #2383776

Reaction equation

8,15-bis(p-biphenylyl)-8,15-dihydro-8,15-dihydroxybenzo[a]-pentacene

hydrogen iodide

sodium hydrogencarbonate

→

deep purple amorphous solid

Yield 51.0%

8,15-bis(p-biphenylyl)benzo[a]pentacene

Yield 51.0%

Solvents

isopropyl ether

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGthe obtained mixture was stirred for 10 minutes
2. 2
   OtherThe formed precipitates
3. 3
   Otherwere separated by filtration
4. 4
   Washwashed once with ion-exchanged water, once with a saturated aqueous solution of sodium disulfite
5. 5
   OtherThe washed precipitates
6. 6
   Otherwere dried
7. 7
   Temperatureunder heating at a reduced pressure and 0.84 g (the yield: 51%) of a light purple solid of 8,15-bis(p-biphenylyl)benzo[a]pentacene
8. 8
   Otherwas obtained
9. 9
   OtherThe obtained product was purified by sublimation at 320° C. under 4.0×10−6 Torr for 2 hours

Procedure

In 150 ml of isopropyl ether and 75 ml of dichloromethane, 1.5 g (2.3 mmole) of 8,15-bis(p-biphenylyl)-8,15-dihydro-8,15-dihydroxybenzo[a]-pentacene was suspended. To the obtained suspension, 40 ml of a 57% aqueous solution of hydrogen iodide was added under the refluxing condition and the obtained mixture was stirred for 5 minutes. After the reaction was completed, the reaction solution was added to 500 ml of a saturated aqueous solution of sodium hydrogencarbonate and the obtained mixture was stirred for 10 minutes. The formed precipitates were separated by filtration and washed once with ion-exchanged water, once with a saturated aqueous solution of sodium disulfite and then three times with ion-exchanged water. The washed precipitates were dried under heating at a reduced pressure and 0.84 g (the yield: 51%) of a light purple solid of 8,15-bis(p-biphenylyl)benzo[a]pentacene was obtained. The obtained product was purified by sublimation at 320° C. under 4.0×10−6 Torr for 2 hours and 450 mg of a deep purple amorphous solid was obtained.

Source