In this article we describe the self-assembling properties of alkyl su
bstituted xylitols in relation to both thermotropic and lyotropic liqu
id crystalline mesophases. Three series of substituted xylitols were p
repared where aliphatic chains of varying length were attached to a xy
litol moiety via ether, thioether and ester linking groups. The thermo
tropic properties were investigated by thermal polarized light microsc
opy and differential scanning calorimetry, and evaluated as a function
of chain length and linking group. The lyotropic phase behaviour was
investigated via the addition of water to each material at room temper
ature. The efficiency for forming thermotropic phases was found to be
reversed for the lyotropic phases in respect of the three series, i.e.
as a function of the linking unit.