1. Synthesis, Metal Ion Complexation, and Emission Studies of Naphthalimide Based Fluoroionophores
Jeffrey E. Elbert, Department of Chemistry and Biochemistry, University of Northern Iowa, Cedar Falls, Iowa, 50614
Fluorescence enhancement of 4-substituted and imide-substituted alkylamino-1,8-naphthalimides upon addition of sub-ppm concentrations of transition metal ions is being investigated for potential use in a variety of systems including trace metal analysis in biochemical and environmental systems. Our study of the acyclic derivatives, including 1°-DETA, found no increase in metal ion selectivity or fluorescence enhancement with increased chain length or additional nitrogens. We are currently finishing synthetic and photochemical studies of 2° amino derivatives (2°-DETA and cyclam/cyclen derivatives), and beginning studies of imide substituted derivatives (Imide-DETA)
We are also studying the photoreaction/photodegradation of 44 in buffered suspensions as a model compound for the more substituted naphthalimides. Our initial observations of irradiations into the charge-transfer band ( nm) include 4-aminonphthalimide as a major product. This suggests an elimination in the excited state. We are currently changing reaction conditions to examine the effects of temperature, pH, and added nucleophiles on the product mixtures. We are also attempting to detect the alkene or alkene addition products by GC-MS.