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Date of Award
Bachelor of Science (BS)
Department of Chemistry and Biochemistry
Kevin L. Caran
M-P,12,12, a triscationic amphiphile, was characterized for its antibacterial and colloidal properties as well as its ability to associate with sodium dodecyl sulfate (SDS). This amphiphile has a mesitylene core, one pyridinium headgroup, and two dimethyldodecylammonium tails. The critical aggregation concentration (CAC) for M-P,12,12 was determined by three different methods. According to isothermal titration calorimetry (ITC), the CAC is 2.54 mM, conductivity studies determined the CAC to be 2.07 and the degree of ionization to be 0.188, and nuclear magnetic resonance (NMR) spectroscopy yielded a CAC value of 1.73 mM. The NMR study of the water-insoluble solid formed by M-P,12,12 and SDS found that the two associate in an approximately 1 to 3 ratio of M-P,12,12 to SDS. In addition to this study, several reactions were undertaken to install either a caffeine or acridine headgroup onto the mesitylene core as well as to produce long-chain amines to be added to M-1,1. These reactions were variably efficient and may or may not warrant future work to optimize conditions.
McKenna, Kristin R., "The synthesis and colloidal characterization of several triscationic amphiphilic antibacterial agents" (2016). Senior Honors Projects, 2010-current. 192.