Synthesis of dye/fluorescent functionalized dendrons based on cyclotriphosphazene

Aurélien Hameau,Jean-Pierre Majoral,Régis Laurent,Anne-Marie Caminade,Sabine Fuchs

doi:10.3762/bjoc.7.186

Abstract

Functionalized phenols based on tyramine were synthesized in order to be selectively grafted on to hexachlorocyclotriphosphazene, affording a variety of functionalized dendrons of type AB5. The B functions comprised fluorescent groups (dansyl) or dyes (dabsyl), whereas the A function was provided by either an aldehyde or an amine. The characterization of these dendrons is reported. An unexpected behaviour of a fluorescent and water-soluble dendron based on dansyl groups in mixtures of dioxane/water was observed.

Highlights

Dendrimers constitute an important group of hyperbranched macromolecules, pertaining both to the field of molecular chemistry thanks to their perfectly defined structure due to their step-by-step synthesis, and to the field of polymers due to their repetitive structure
We report here the use of hexachlorocyclotriphosphazene (N3P3Cl6) for such a purpose, which allows the gathering of five fluorescent dansyl groups in a small dendron, thanks to the specific functionalization of N3P3Cl6 [15]
Dendrons 8 and 9 are soluble in organic solvents, as is dendron 10, but in the case of 10 it is soluble in water in contrast to the others, we studied its fluorescence in water

Summary

Introduction

Dendrimers constitute an important group of hyperbranched macromolecules, pertaining both to the field of molecular chemistry thanks to their perfectly defined structure due to their step-by-step synthesis, and to the field of polymers due to their repetitive structure. We report here the use of hexachlorocyclotriphosphazene (N3P3Cl6) for such a purpose, which allows the gathering of five fluorescent dansyl groups in a small dendron, thanks to the specific functionalization of N3P3Cl6 [15]. The first step of the strategy entails the non-symmetrical functionalization of hexachlorocyclotriphosphazene (N3P3Cl6) in order to synthesize AB5-type compounds, where A is the function usable, for instance, for the coupling with another dendron, and the B functions are either the dyes or the fluorescent groups.

Results

Conclusion