Phosphorus-Nitrogen Compounds: Part 25. Syntheses, Spectroscopic, Structural and Electrochemical Investigations, Antimicrobial Activities, and Dna Interactions of Ferrocenyldiaminocyclotriphosphazenes

Abstract

The condensation reactions of hexachlorocyclotriphosphazene (N3P3Cl6) with mono (1 and 2) and bisferrocenyldiamines (3-5 and 7) resulted in the formation of tetrachloro mono- (8 and 9) and bisferrocenylspirocyclotriphosphazenes (10-13). In addition the tetramorpholino mono- (8a and 9a) and bisferrocenylphosphazenes (10a-12a) were obtained from the reactions of the corresponding tetrachlorophosphazenes (8-12) with excess morpholine. The structures of all the phosphazenes were determined using FTIR, MS, H-1, C-13, and P-31 NMR and 2-dimensional NMR techniques. The structures of 9a and 13 were determined by single crystal X-ray diffraction techniques. Cyclic voltammetric investigations of compounds 8a, 9a, and 11a revealed that ferrocene redox centers undergo reversible oxidation. These ferrocenylphosphazenes appear to be quite robust electrochemically. Interactions between the compounds 8a, 9a, 11a, and 12a and pBR322 plasmid DNA were investigated by agarose gel electrophoresis. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]