Chiral N-Substituted Perylene-3,4-dicarboximides as Fluorescent Labeling Reagents

Chiral N-substituted perylene-3,4-dicarboximides have been synthesized. These optically pure compounds were sufficiently soluble in acetonitrile used as fluorescent labeling reagents. Their excitation and emission maxima were observed at λ 500 and 550 nm in acetonitrile, respectively. Enantiomers in a racemic mixture could be analyzed by these reagents. Racemic Ibuprofen and alanine methyl ester were nicely separated by (R)-N-(2-hydroxy-1-phenylethyl)- and (R)-N-(α-carboxyphenethyl)perylene-3,4-dicarboximides in HPLC, respectively. The detection limits (S/N > 3) of Ibuprofen and alanine methyl ester were 1 and 13 pmol, respectively.