Tripodal bile acid architectures based on a triarylphosphine oxide core obtained by copper-catalysed [1,3]-dipolar cycloaddition: Synthesis and preliminary aggregation studies

We report the synthesis and aggregation behaviour of new water-soluble, bile acid derived tripodal architectures based on a core derived from triphenylphosphine oxide. We employed the well-established copper-catalysed [1,3]-dipolar cycloaddition (CuAAC) for the construction of these tripodal molecules. The aggregation behaviour of these molecules in aqueous media was studied by different analytical methods such as dye solubilisation, dynamic light scattering, NMR and AFM. These molecular architectures also offer an additional advantage in aiding understanding of the influence of the nature of the bile acid backbone and of the configuration at the steroid C-3 position in these architectures; to the best of our knowledge this has not been reported in the literature. The unique gelation properties of the α-derivatives were explained through molecular modelling studies and the mechanical behaviour of these gels was studied by rheology experiments.