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, ¹H, ¹³C, and ³¹P 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.

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GRAPHICAL ABSTRACT

Keywords::

• Ferrocenylphosphazenes
• syntheses
• spectroscopy
• crystal structure
• DNA interactions
• electrochemistry

Acknowledgments

The authors acknowledge the “Scientific and Technical Research Council of Turkey” Grant No. 108T892. L. Açık thanks to the State Planing Organization (Grant No. 1998K121480). T. Hökelek is indebted to “Hacettepe University, Scientific Research Unit” (Grant No. 02 02 602 002) for their financial support.