Synthesis and photochemistry of cyclam-4

CHED 466

Rebecca L. Wilson, acceber@uni.edu and Jeffery E. Elbert. Department of Chemistry and Biochemistry, University of Northern Iowa, McCollum Science Hall, Cedar Falls, IA 50614

The purpose of this research was to develop a highly-selective, highly-sensitive fluorescence-based sensor for sub-ppm levels of transition metals. N-butyl-4-(1,4,8,11-tetraazacyclotradecane)-1,8-napthalimide (cyclam-4) was synthesized and tested in various conditions in an attempt to quench fluorescence and create a metal tracer. The four nitrogens of the unique ring structure were hypothesized to increase fluorescence quenching as well as serve as a highly-selective tracer. The addition of cyclam to the 4-position of a 1,8-naphthalimide fluoroionophore did not quench fluorescence with the addition of metals as effectively as expected. It is possible that the cyclam ring is selective for a metal that has not been tested to date. The results suggest that Cu2+ has the strongest complexing ability with the cyclam ring.