Uses
1-Acetylpyrene is suitable for use in a comparative study on the photoinitiating efficiency of pyrene, 1-acetylpyrene and 1-(bromoacetyl)pyrene for copolymerization of styrene with acrylonitrile. It may be used in the following studies:
- As a starting material in the synthesis of ethynlypyrene. 1-(1-chlorovinyl)pyrene was also isolated during this reaction.
- As a starting material in the synthesis of substituted pyrene derivatives incorporated heterocyclic and sugar moieties.
- Synthesis of (E)-pyrene oxime ester conjugates of carboxylic acids.
- Synthesis of tertiary alcohols based on 1-acetylpyrene.
- Synthesis of (E)-N-[1-(pyren-1-yl)ethylidene]chrysene-2-amine.
- Synthesis of 3,3-di(methylsulfanyl)-1-(1-pyrenyl)-2-propen-1-one.
General Description
1-Acetylpyrene is a pyrene derivative. Its synthesis has been reported. Its phytophysical properties have been studied using absolute fluorescence quantum yield measurement and time-dependent density functional theory (TD-DFT) calculations. Its ability to interact with human cytochromes P450 2A13, 2A6, and 1B1 and enzyme inhibition has been reported. Its function as an environment-sensitive fluorophore has been investigated.
Synthesis
Preparation of 1-acetylpyrene: pyrene was mixed with dichloromethane under dry condition according to 1 mmol:10 ml, stirred to dissolve, and anhydrous aluminum trichloride was added under dry condition; acetyl chloride was added into dichloromethane drop by drop in an ice-water bath, and the drop acceleration was controlled to be one drop in 3-5 seconds, and the ratio of acetyl chloride and dichloromethane was 7 mmol:10 ml; and then acetyl chloride was added into the pyrene solution with anhydrous aluminum trichloride drop by drop, the reaction was followed by TLC for 12h at room temperature. Then the acetyl chloride solution was added dropwise into the solution of pyrene and anhydrous aluminum trichloride, the ice water bath was withdrawn, and the reaction was stirred at room temperature for 12h, the reaction was tracked by TLC, and the unfolding agent was dichloromethane and petroleum ether at the ratio of 1:2 by volume, and the color of the solution was changed from dark green to dark green. The product was separated by silica gel column chromatography to obtain light yellow 1-acetylpyrene.
