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Article Dans Une Revue ChemPlusChem Année : 2023

The Chemistry of P=N−P=X (X=S, O, NR) Linkages for the Synthesis of Dendritic Structures

Résumé

The Staudinger reaction between a phosphine and an azide, applied to phosphorus azides, has been used for the synthesis of a large variety of dendritic structures, incorporating P=N−P=X moieties (X = mainly S, but also O and N−R). Conjugation of the P=N bond with the P=X bond greatly stabilizes the P=N bond. Highly branched structures such as dendrons, dendrimers, Janus dendrimers, layered dendrimers, surface-block dendrimers, and diverse other dendritic structures incorporating such linkage have been elaborated. Accelerated methods of synthesis of dendrimers are also based on the Staudinger reaction. A versatile reactivity was observed exclusively on the sulfur atom of P=N−P=S linkages, such as alkylation or complexation. Alkylation on S induces a weakening of the strength of the P=S bond, which can be easily cleaved to generate phosphines able to react in Staudinger reactions inside the structure of dendrimers, thus affording highly sophisticated dendritic structures.
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Dates et versions

hal-04064179 , version 1 (11-04-2023)

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Valérie Maraval, Régis Laurent, Anne‐marie Caminade. The Chemistry of P=N−P=X (X=S, O, NR) Linkages for the Synthesis of Dendritic Structures. ChemPlusChem, 2023, 88 (4), pp.e202300064. ⟨10.1002/cplu.202300064⟩. ⟨hal-04064179⟩
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