Optimized synthesis of selected 4-oxybenzaldehyde and 2,2-dioxybiphenyl cyclotriphosphazene derivatives

Abstract

Selected 4-oxybenzaldehyde and 2,2-dioxybiphenyl cyclotriphosphazene derivatives were synthesized via substitution reactions through tailored control. The reactions of cyclotriphosphazene with 4-oxybenzaldehyde and 2,2-dioxybiphenyl gave the following synthesized derivatives: one mono-substituted open-chain compound, N₃P₃Cl₅(O₂C₇H₅) (1, 69%); mono spiro, N₃P₃Cl₄(O₂C1₂H₈) (2, 91.1%); non-gem tri-substituted, N₃P₃Cl₃ (O₆C₂₁H₁₅) (3, 17%); dispiro, N₃P₃Cl₂(O₄C₂₄H₁₆) (4, 92.3%); penta-substituted, N₃P₃Cl(O₁₀C₃₅H₂₅) (5, 92%)；hexa-substituted, N₃P₃(O₁₂C₄₂H₃₀). Most of these derivatives (1–6) are obtained with good yield (up to 97%), This work provides a simple and available approach to obtain versatile cyclotriphosphazene derivatives, which is expected to further promote the use of HCCP as phosphorus platform for the construction of multi-functional materials.

Graphical Abstract

Keywords:

• Hexachlorocyclotriphosphazene (HCCP)
• tailored control
• ³¹P NMR

Acknowledgment

We thank the Innovation Program of University students of Shanghai Higher Education Institutions (cs1804002) and the Sino-French Cai Yuanpei Program.

Additional information

Funding

We thank the Innovation Program of University students of Shanghai Higher Education Institutions (cs1804002) and the Sino-French Cai Yuanpei Program.