Synthesis of N,N',N"-Triaryl Derivatives of Tris(3-aminopropyl)amine and Their Study as Fluorescent Detectors of Metal Cations

Palladium-catalyzed arylation of tris(3-aminopropyl)amine (TRPN) with several halogen-substituted naphthalene, anthracene, phenanthrene, and pyrene was studied. As a result, corresponding N,N,N"-triaryl derivatives were synthesized, and the best yields of the target compounds were obtained in the reactions with 1-chloro- and 9-bromoanthracenes. Fluorescence spectra of these compounds were studied in the presence of metal cations which showed that complete or very strong quenching of emission was observed upon the addition of Cu(II), Al(III), Cr(III) perchlorates in the case of 1-naphthyl-, 2-anthryl-, and 9-phenanthrenyl derivatives of TRPN. For 1-pyrenyl derivative complete quenching of fluorescence took place only in the presence of copper cations. For a number of other metal cations, slight changes in the emission intensity were observed with hypsochromic shifts of the maximum by approximately 10 nm. The characteristic changes in the absorption spectra of compounds 2, 5, 8 were observed in the presence of Cu(II), Al(III), and Cr(III) cations, which make these compounds promising for fluorescent and spectrophotometric detection of Cu(II), Al(III), and Cr(III) cations.