Date of Award

11-1-2023

Language

English

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

College/School/Department

Department of Chemistry

Dissertation/Thesis Chair

John T Welch

Committee Members

Jeremy I Feldblyum, Ting Wang, Gabriele Fuchs

Subject Categories

Chemistry

Abstract

Fluorine atom was widely applied in the organic chemistry and medicinal chemistry due to its strong electronegativity and lipophilicity. Fluorine atom, trifluoromethyl (CF3) moiety, trifluoromethyl sulfenyl (CF3S) moiety, pentafluoromethylsulfenyl (SF5) moiety have already been applied in the medicinal chemistry. These fluorinated groups brought the good chemical stability, oral stability, low toxicity, and longer half-life compared with the analogs. Fluorine containing compounds can be synthesized via radical reaction, electrophilic fluorinated source as well as nucleophilic sources. Additionally, the fluorinated compounds can also be synthesized via chlorofluoro-oxidation and SN2 reactions. In our lab, we introduced the super fluorine rich moiety (trans-CF3SF4 group) to different substrate. trans-CF3SF4Cl was synthesized in our lab with the chlorofluoro-oxidation process with CF3SSCF3. We firstly synthesized the fluorinated amines, and herein we reported that trans-CF3SF4 group alter the chemical features of the traditional amines compounds such as basicity and lipophilicity. Additionally fluorinated groups help the formation of alpha helix structure of peptoid, thus we also reported the synthesis of fluorine group containing peptide-peptoid sequences. Fluorinated groups were used in the synthesis of nucleoside compounds, and the fluorinated group provided the better chemical stability and oral absorption. Compared with C5’-fluorinated nucleoside we synthesized the analog containing trans-CF3SF4 group. Introduction of fluorinated group can be a challenge. Cross metathesis is an atom-economic and efficient method of introduction of functional group. Fluorinated groups can be introduced to various substrate via cross metathesis. Herein we reported the successful cross metathesis of fluorine-rich olefins, and the method provides an ideal method to expand the categories of fluorinated compounds. Fluorinated moieties were applied in the synthesis of polymers because of its high surface energy providing the good hydrophobicity. Wide variety of fluorinated polymers are synthesized and applied in the daily life. Our lab reported an important fluorinated polyacrylate and the tested results showed good thermal stability and hydrophobicity, and these features implies the further applications of our fluorinated polymers.

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