Preparation of 9,10-Phenanthrene Oxide and its Derivatives
Sensors are very important in everyday life as well as for scientists in the lab. They can be sensing dangerous chemicals to help save someone’s life, or they can perform tasks to help scientists learn, such as measure the fluorescence of a molecule. 1,10-phenanthroline is a bidentate nitrogen ligand that readily binds to metals and is useful in coordination chemistry. Derivatives of 1,10-phenanthroline can be useful in almost any type of chemistry, because they bind so readily to metals. Fluorescence sensors can help determine how the 1,10-phenanthroline derivatives bind, or whether or not the molecule is bound through the nitrogens at the 1- and 10-positions. This is tested by measuring the fluorescence of both the derivatives of 1,10-phenanthroline and phenanthene, a molecule of similar structure lacking the nitrogens at the 1- and 10- positions, and comparing them. Derivatives of these two molecules can be formed via an epoxide to fit the needs of many situations. Different experimental conditions were tested and the best way to form the 1,10-phenanthroline-5,6-epoxide is with a pH of 8.6- 8.8, use quality bleach (Clorox), and to not let the reaction go for too long. These conditions were applied to forming 9,10-phenanthrene and were successful, though in only a 42% yield. Further work needs to be done to synthesize pure derivatives of 9,10- phenanthrene oxide and compare their fluroescencies to similar derivatives of 1,10- phenanthroline-5,6-epoxide.