Monofunctional amines substituted fluorenylidene bridged cyclotriphosphazenes: 'Turn-off' fluorescence chemosensors for Cu2+ and Fe3+ ions

Abstract

In the present work, the reaction of 2,2,4,4-tetra(anilino)-6,6-dichlorocyclotriphosphazene (4) and 2,2,4,4-tetra(2-naphthylamino)-6,6-dichlorocyclotriphosphazene (5) with 4,4'-(9-fluorenylidene)diphenol, FDP, (6) and 4,4'-(9-fluorenylidene)dianiline FDA (7) were studied in THF and new aniline (8 and 9) and 2-naphthylamine (10 and 11) substituted FDP-bridged cyclotriphosphazenes and aniline (12) and 2-naphthylamine (13) substituted FDA-bridged cyclotriphosphazene derivatives were obtained. All newly synthesized monofunctional amines substituted fluorenylidene bridged cyclotriphosphazenes (8-13) were fully characterized by elemental analysis, H-1 and P-31 NMR spectroscopies, MALDI-TOF mass spectrometry and UV-Vis electronic absorption spectra. The florescence properties of the synthesized new compounds were studied. The chemosensory behavior of the compounds against to metal ions was also investigated. The obtained fluorenylidene bridged 2-naphthylamine substituted cyclotriphosphazenes (10, 11 and 13) showed fluorescence chemosensor behavior with high selectivity for Fe3+ and Cu2+ ions in the solution. (C) 2015 Elsevier Ltd. All rights reserved.