Date of Award

1-2016

Document Type

Thesis

Degree Name

Master of Science (MS)

College/School

College of Science and Mathematics

Department/Program

Chemistry and Biochemistry

Thesis Sponsor/Dissertation Chair/Project Chair

Saliya A. de Silva

Committee Member

John L. Isidor

Committee Member

David W. Konas

Abstract

The development of novel fluorescent sensors for cations is an area of current interest. Most of these sensors are large organic molecules that have a low solubility in water and are not suitable to be used as sensors in water. The goal of this study is to develop a new sensor by attaching an ionic liquid group to make it water-soluble. We have used a well-known photoinduced electron transfer (PET) sensor for protons as our first test. This sensor is based on a chromophore-spacer-receptor design that is based on an anthracene chromophore and a morpholine proton receptor. The sensor is nonfluorescent at high pH due to PET between the tertiary nitrogen atom of the receptor and the chromophore. The PET can be quenched by protonation of the nitrogen atom leading to a fluorescent signal at low pH. As this sensor is not water-soluble all fluorescence studies have been carried out in methanol water mixtures. In this study, we have attached a methyl imidazolium group to the anthracene to make this sensor a water-soluble ionic liquid. The new sensor was prepared by selectively functionalizing the 9 and 10 positions of an anthracene and the fluorescence studies of the new ionic liquid based sensor were carried out in water.

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