New Approaches Towards Monoamino Polyglycerol Dendrons and Dendritic Triblock Amphiphiles

In order to improve the water solubility of nonpolar compounds such as drugs or dyes, new amphiphilic molecules are needed. In this paper we describe a new class of triblock amphiphiles that we have synthesized by a straightforward convergent approach. These amphiphiles each consist of a nonpolar biphenyl core and a polar shell based on various generations of monoamino polyglycerol dendrons, coupled to the core through amide linkages (1). For the synthesis of these monoamino dendrons we applied a simple iterative two‐step process based on allylation of an alcohol group and catalytic dihydroxylation. As starting materials, D,L‐serine/serinol and – in a second, similar pathway – commercially available triglycerol were used. The transport behavior of these defined triblock amphiphiles was then investigated with the nonpolar dye Nile Red in water.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)