Synthesis and characterization of (S)-BINOL-modified cyclotriphosphazene tetradentate ligands

GRAPHICAL ABSTRACT

ABSTRACT

Three novel cyclotriphosphazene derivatives were synthesized by the reaction of hexachlorocyclotriphosphazene (HCCP) with (S)-BINOL and the potassium salt of 4-hydroxybenzaldehyde, and subsequent reduction of aldehyde groups to alcohol groups using sodium borohydride. The bromination reaction was carried out using PBr₃ to give N₃P₃(O₂C₂₀H₁₂)(OC₆H₄-p-CH₂Br)₄ (3). The target ligands were obtained by the reaction of compound 3 with morpholine, imidazole, and pyrazole, respectively. Structure of title compounds were characterized by ¹H NMR, ¹³C NMR, ³¹P NMR, and ESI-MS. The Cu complex of 4 was effective in the cleavage of pUC19 DNA under physiological conditions.

KEYWORDS:

• Cyclotriphosphazene derivatives
• (S)-BINOL
• hexachlorocyclotriphosphazene

Funding

This work was financially supported by the NSFC (no. 21572209), He'nan Scientific Committee (152102410018), and Foundation of He'nan Educational Committee.