pyren-1-amine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-aminopyrene (5 g), potassium carbonate (15 g) and ethyl 6-bromohexanoate (10 g) in 60 mL acetonitrile was refluxed for 24 hours. The solvent was removed and the product was purified by a silica gel column eluting with EtOAc/hexane. was refluxed for 24 hours The solvent was removed the product was purified by a silica gel column eluting with EtOAc/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-aminopyrene (5 g), potassium carbonate (15 g) and ethyl 6-bromohexanoate (10 g) in 60 mL acetonitrile was refluxed for 24 hours. The solvent was removed and the product was purified by a silica gel column eluting with EtOAc/hexane. was refluxed for 24 hours The solvent was removed the product was purified by a silica gel column eluting with EtOAc/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-aminopyrene (5 g), potassium carbonate (15 g) and ethyl 6-bromohexanoate (10 g) in 60 mL acetonitrile was refluxed for 24 hours. The solvent was removed and the product was purified by a silica gel column eluting with EtOAc/hexane. was refluxed for 24 hours The solvent was removed the product was purified by a silica gel column eluting with EtOAc/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,6-dioxaoctanedioic acid (0.28 mmol) was dispersed in 100 ml of dichloromethane (CH2Cl2) in which 0.1 ml of oxalyl chloride ((COCl)2) and 15 μl of DMF were added, to prepare a solution. After the solution was stirred at ambient temperature for 4 hours, volatiles were removed from the solution and the residue was re-dissolved in a small amount of dichloromethane. After the solution was added slowly to dichloromethane solution in which 152 mg (0.70 mmol) of 1-aminopyrene and 0.2 ml (1.4 mmol) of triethylamine were dissolved, the solution was reacted at ambient temperature for 4 hours and the volatiles were removed. And then, the resulting product was partitioned between water and dichloromethane and the organic phase was separated and washed with water; the solvent was removed from the obtained organic phase; and then, re-crystallization was carried out with a solvent combination of dichloromethane and methanol. The target product, a pyrene compound of 3,6-dioctanedioic acid was obtained (reddish green solid, yield: 65%). were added to prepare a solution volatiles were removed from the solution the residue was re-dissolved in a small amount of dichloromethane were dissolved the solution was reacted at ambient temperature for 4 hours the volatiles were removed And then, the resulting product was partitioned between water and dichloromethane the organic phase was separated washed with water the solvent was removed from the obtained organic phase and then, re-crystallization

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. the following dyes were prepared the crude product was collected by filtration washed with 20 mL cold water dried under argon

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-aminopyrene (5 g), potassium carbonate (15 g) and ethyl 6-bromohexanoate (10 g) in 60 mL acetonitrile was refluxed for 24 hours. The solvent was removed and the product was purified by a silica gel column eluting with EtOAc/hexane. was refluxed for 24 hours The solvent was removed the product was purified by a silica gel column eluting with EtOAc/hexane