1-Aminopyrene → HCID 21464477, compound

Participants

Reaction Steps

Dyes 2a, 2d and 3 were obtained from Eastman, and the following dyes were prepared as described previously: 2c (8); 2g (9). The syntheses of 2e, 2f, 2h, 2I and 2j were modeled after the sulfonation procedures described in (10). Thus, for 2f, a solution of finely powdered 1-aminopyrene (869 mg, 4 mmol) in 10 ml chlorosulfonic acid was stirred under argon atmosphere for 10 hours at room temperature. The solution was poured on 30 g of crushed ice and the crude product was collected by filtration, washed with 20 mL cold water and dried under argon to give 1.4 g of 8-amino-1,3,6-pyrenetrisulfonylchloride (69%). Hydrolysis of this chloride in basic water (NaOH, pH 8) gave a solution of 2f (8-amino-1,3,6-pyrenetrisulfonate). Analogous procedures were used to prepare 2g-2j, except replacing the 1-aminopyrene with the appropriate substituted pyrene starting material.

Provenance & Evidence