PREPARATION, CRYSTALLINE-STRUCTURE, AND SPECTRAL PROPERTIES OF FLUORESCENT-PROBE 4,4=-BIS-1-PHENYLAMINO-8-NAPHTHALENESULFONATE

A method for the preparation and purification of the covalent dimers of 1-phenylamino- and 1-toluidylaminonaph-thalenesulfonic acids is described. X-ray analysis of the crystals of the potassium salt of the former (bis-ANS) showed this to be 4,4'-bis-1-phenylaminonaphthalene-8-sulfonate. By similarity of the NMR spectra and optical properties the second dimer is recognized to be 4,4'-bis-1-toluidylaminonaphthalene-8-sulfonic acid. NMR spectra, molar absorption coefficients, fluorescent lifetimes, and the detailed structural parameters derived from the x-ray data are presented. Some of the uses of the compounds as fluorescent probes in solutions and crystals of proteins are briefly discussed. © 1978, American Chemical Society. All rights reserved.