I belong to a bio-organic laboratory and study organic chemistry and supramolecular chemistry almost every day. In my laboratory, I often experiment with my study theme. I will introduce you to my study theme.
In 1967, Charles John Pedersen, who worked for DuPont in the United States and received a Novel prize in chemistry in 1987, reported that crown ethers, which are a kind of the organic compounds, captured a metal cation. These compounds are cyclic compounds containing a number of ether chains and can capture a metal cation which a diameter of the cation is as large as the size of the crown ether ring. They are expected to be used as selective chemical sensors for a metal cation.
Our group has studied about a synthesis of crown ethers containing dye compounds for a long time. Because they contain dye compounds, a color of the solution containing a target molecule which our group wants to synthesize will change another color when a target molecule captures a certain metal cation. When a synthesis of the target molecule is succeeded, this compound will be expected to be used as an optical chemical sensor for a certain metal cation. A target molecule which I want to synthesize contains naphthoquinone skeletons as dye compounds. Therefore, my study theme is to synthesize a dye compound of crown ethers containing naphthoquinone structures.
To synthesize the target molecule, I made a synthetic design which consists of five steps and experimented along this design practically. First step was mesylation of diethylene glycol, second step was O-alkylation of p-nitrophenol, third step was reduction of two nitro group, fourth step was diazotization of two amino groups and final step was arylation of 1,4-naphothoquinone which is called Meerwein arylation. As the result of these steps, I could obtain the compounds which was generated from first to fourth step but I couldn’t obtain the target molecule which was generated by final step. Currently, I am carrying out final step under a variety of conditions again. If the target molecule was obtained by final step, I would analyze the ability of the target molecule which captures a metal cation.