Synthesis and characterization of dendritic structures incorporating phosphorus, sulfur, and silicon

GRAPHICAL ABSTRACT

ABSTRACT

Two new families of small phosphorus-containing dendrons, having as core either a phenol protected by a t-butyldimethylsilyl group or a terminal alkyne protected by a trimethylsilyl group have been synthesized. Both families comprise P, S, and Si (and other elements) in their structure. The structure of one of the smallest dendron, having a P(S)Cl₂ terminal group, has been determined by X-ray crystallography, showing an almost planar arrangement of a large part of the structure. The P(S)Cl₂ terminal group is particularly suitable for further functionalization, as illustrated by the grafting of amines, aldehydes, and dansyl derivatives. These functions were grafted thanks to the reactivity of amines and phenols in basic conditions, demonstrating the compatibility of these reactions with the presence of the protecting groups. Deprotection attempts proved to be difficult, in particular for the purification of the deprotected products. All compounds have been characterized at least by ¹H, ¹³C, and ³¹P NMR.

KEYWORDS:

• Dendron
• dendrimer
• protection/deprotection
• phosphorus

Funding

We thank the CNRS for financial support, and also the COST action CM1302 SIPs.