A surfactant is an amphiphile which consists of a hydrophobic and hydrophilic end. In nonpolar solvents containing a small amount of water surfactants can form reverse micelles. Extensive research has been done using fluorescent probes to study several properties of these amphiphilic aggregates including mechanism of formation, critical micelle concentration, aggregate number and size, nanopolarity, and viscosity. Dr. Langner's group at RIT proposed the structure of a difluorometric, ratiometric probe that can transverse the membrane of a reverse micelle created in a system of decane/water/AOT/butyl alcohol. This probe has a dansyl and a coumarin portion making it amphiphilic and could advance future studies in the formation of reverse micelles and the kinetics of their interactions with other compounds. Use of a difluorometric probe helps eradicate the limitations of previously utilized single fluorophore-containing probes involving both their interactions with the aqueous medium, and pinpointing the location in the reverse micelle system. My research focused on the synthesis and combination of the dansyl chloride and the 7-amino-4-methyl coumarin species through derivatization chemistry of an acid chloride into an amide. This thesis will serve to highlight various synthetic methods employed by previous undergraduate students in the Collison group as well as my work towards the synthesis of the difluorometric compound which can serve as a probe for various amphipathic systems including reverse micelles. The derivatization chemistry to successfully synthesize this molecule is covered in detail and two difluorometric probes with varying hydrocarbon chain lengths are reported.
Library of Congress Subject Headings
Molecular probes; Micelles; Surface active agents--Analysis
Department, Program, or Center
School of Chemistry and Materials Science (COS)
Raymond, Danielle, "Synthesis of a difluorometric cross-membrane molecular probe for studying amphipathic systems" (2012). Thesis. Rochester Institute of Technology. Accessed from
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