Document Type

Poster

Publication Date

2016

Disciplines

Biochemistry | Chemical and Pharmacologic Phenomena | Medicine and Health Sciences | Organic Chemicals | Pharmaceutical Preparations

Abstract

Palladium is often used in the synthesis of Active Pharmaceutical Ingredients (APIs), although it is toxic to ingest. As it is difficult to remove, it is imperative to develop optimal palladium sensors that can be utilized in quality control of pharmaceutical synthesis in order to ensure that all residual palladium catalyst is removed from APIs. The goal of this project is to study a novel series of phenolic fluorophores in order see which, if any, are capable of functioning as palladium sensors. Through a Tsuji-Trost substitution reaction, palladium functions as a catalyst that facilitates the removal of the allyl group from these phenolic compounds and produces a fluorescent molecule that can be quantified. The fluorescence signals of these product compounds were measured over using a Carey Eclipse Fluorimeter in the organic chemistry laboratory at Wabash College. Each phenolic compound was introduced to seven different solutions of varying concentrations of palladium and immediately placed in the Fluorimeter for analysis. The initial rates of the deallylation reaction were measured over 15 minutes, which tells us at what concentrations of palladium the phenolic compound can be distinguished from the blank and be considered an effective palladium sensor. The lower limits of detection amongst these four compounds allowed us to determine the effects that additional functional groups had on the palladium sensing capabilities of these fluorophores. The unsubstituted compound fluoresced more and at an increased initial rate than either the bromo- or methoxy-substituted compounds at every concentration of palladium. However, the unsubstituted compound also fluoresced more over time in the absence of palladium, which is not ideal for a palladium sensor, while the substituted compounds only fluoresced in the presence of palladium. Future work should be directed towards introducing weakly electron-withdrawing groups to the unsubstituted compound in order to optimize its palladium sensing capabilities.

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