Synthesis and assembly properties of a series of chiral amphiphilic dihydroxytetrahydrofuran derivatives

The synthesis of a series of amphiphilic dihydroxytetrahydrofuran derivatives, prepared from isomannide and isosorbide, possessing hydrophobic ether chains lengths varying from C-10 to C-18 attached ct to the tetrahydrofuran ring and with R and S chirality at the 0 linkage carbon atom is described. The interfacial properties of these compounds were studied using a Langmuir film balance; the results showed the expected increase in film stability with increasing chain length and differences in phase behaviour and film stability related to linkage chirality. The formation of colloidal dispersions of these compounds was studied both dynamic light scattering and non-contact mode atomic force microscopy. Copyright (C) 2000 John Wiley & Sons, Ltd.