Three novel tris(macrocycle)s having fluorescent residues at their distal termini have been prepared and studied. The compounds are of the form 2), and dansyl (3). Compounds 2 and 3 were found to transport Na + at rates similar to those of other tris(macrocyclic)s but 1 was not an ionophore in the bilayer as assessed by 23 Na NMR analysis. The latter failure may be due to a hydrogen-bond blockade leading to a globular conformation adopted by the hydraphile. The fluorescence maximum of 3 was determined in a variety of solvents and in a phospholipid bilayer. The polarity experienced by the dansyl group in the bilayer was intermediate between that observed in methanol and ethanol. Fluorescence depth quenching using doxylsubstituted lipids showed that the dansyl headgroups of 3 were 14 Å from the bilayer's midplane or separated by about 28 Å. Fluorescence energy transfer between 2 and 3 showed that these two hydraphiles were not appreciably aggregated in the bilayer.