Preparation of 9,10-Phenanthrene Oxide and its Derivatives
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Authors
Hyatt, Chaz B.
Issue Date
2013
Type
Thesis
Language
en_US
Keywords
Alternative Title
Abstract
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.
Description
27 p.
Citation
Publisher
Kalamazoo College
License
U.S. copyright laws protect this material. Commercial use or distribution of this material is not permitted without prior written permission of the copyright holder. All rights reserved.