Date of Award

Fall 12-2019

Degree Type

Honors College Thesis


Chemistry and Biochemistry

First Advisor

Karl Wallace

Advisor Department

Chemistry and Biochemistry


Siderophores are molecules capable of binding ferric ions with high affinity (Ka = 1052). This thesis outlines our attempts to synthesize an artificial siderophore, which incorporates a signaling group to help monitor the uptake of ferric ions. The artificial siderophore is a tripodal molecular receptor synthesized in a five-step procedure with a proposed final sixth step. Rhodamine 6G azide (95.0% yield) was formed from rhodamine 6G and the synthesis of 2-azidoethanamine was modified from the literature. The tripodal arm portion of the sensor was successfully synthesized by protecting the catechol of 2,3-dihydroxybenzaldehyde to form 3-formyl-1,2-phenylene dimethanesulfonate (98.8% yield). The reduction of the aldehyde in the previous compound to a primary alcohol formed 3-(hydroxymethyl)-1,2-phenylene dimethanesulfonate (86.6% yield), which then underwent a nucleophilic substitution to yield 3-(bromomethyl)-1,2-phenylene dimethanesulfonate (80.0% yield). The product of the nucleophilic substitution then successfully underwent a bimolecular nucleophilic substitution to yield the mesyl protected tripodal arm (76.8% yield).