Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregationElectronic supplementary information (ESI) available: Analysis including 1H and 13C NMR of each compound and microscopy images. See DOI: 10.1039/c4ob02191f

In this article we describe work on the synthesis of bolaphile biomimics composed of glucose head groups and steroidal units linked together by a methylene chain of varying length. The condensed phases formed by self-organization of the products as a function of temperature were characterized by differential scanning calorimetry and thermal polarized light microscopy. The results of these studies show that the thermal stabilities of the lamellar mesophases formed vary linearly as a function of increasing aliphatic composition, which reflects a linear hydrophobic-hydrophilic balance with respect to transition temperatures. The synthesis of glycosteroidal bolaphile biomimics are described along with the liquid-crystalline behaviours as a function of increasing aliphatic composition.