Hexa-arm star shaped hydrazone derivatives from hexakis(4-formylphenoxy)-cyclotriphosphazene core

A series of novel hexasubstituted cyclophosphazene hydrazones [N3P3(OC6H4pCHNNHC(O)C6H4pX)6] (X = H, Br, Cl, F, OH, OCH3, CH3, NO2, NH2) were prepared by a sixfold condensation reaction of [N3P3(OC6H4pCHO)6] with para-substituted benzoic hydrazides [NH2NHC(O)C6H4pX] with excellent yields (91–98%). The structures of the compounds were confirmed by elemental analysis, FT-IR, 1H, 13C, 31P, 2D-HSQC NMR and mass spectrometry (MALDI-TOF). All the synthesized cyclophosphazene hydrazones exhibit high thermal stability. The crystal structure of a homogeneously substituted hexakis(4-formylphenoxy)-cyclotriphosphazene was determined by X-ray diffraction analysis. The compound crystallizes in the monoclinic system, space group P21/n with a = 16.558(3) Å, b = 10.250(2) Å, c = 23.429(5) Å, α = γ = 90.00°, β = 90.461(4)°, V = 3976.5(14) Å3 and Z = 4. The R value is 0.0823 for 4290 observed reflections. The conformations of the 4-formylphenoxy-groups are different at the three phosphorus atoms.

► Crystal structure analysis of hexakis(4-formylphenoxy)-cyclotriphosphazene reported. ► Conformations of the 4-formylphenoxy-groups are different at the three phosphorus atoms. ► Novel hexasubstituted cyclophosphazene hydrazones synthesized. ► Several spectroscopic techniques used for structure determination.