P. Baret et al., TRIPODAL LIGANDS POSSESSING 6 CONVERGENT HYDROXYL-GROUPS A NOVEL FAMILY OF IRON SEQUESTERING AGENTS BASED ON O,O'-DIHYDROXYBIPHENYL SUBUNITS, Tetrahedron, 50(7), 1994, pp. 2077-2094
A new family of iron(III) sequestering agents has been designed. Tripo
dal ligands possessing six convergent hydroxyl groups have been prepar
ed by condensation of an appropriate o,o'-biaryl building block and a
spacer. The preparations of building blocks and of simple bidentate li
gands designed for comparative studies are described : several methods
have been used for ortho functionalisation and for 3,3'-difunctionali
sation of 2,2'-dihydroxybiphenyl. Sulfonation of the ligands led to wa
ter soluble agents. These ligands offer an alternative to synthetic hy
droxamate or catecholate siderophores. The hexamethoxylated tripodal p
recursors and their complexing ability towards alkali cations are also
described. The complexing abilities of hexahydroxylated sequestering
agents towards iron(III) are comparable to those of hydroxamate sidero
phores but are lower than those of catecholate siderophores.