Several symmetrical, linear dimers and some star-like tetramers were prepared using easily accessible oxa-bridged derivatives as central rigid cores. In order to produce new liquid crystalline materials various mesogenic/promesogenic groups, containing biphenyl-4,4′-diol, 4,4′-(diazene-1,2-diyl)diphenol and cholesterol sub-moieties, were connected through oxy-ethylene linkers via an ester linkage, in the end-on fashion. Their thermal behaviour and mesomorphic properties were investigated by differential scanning calorimetry (DSC), polarized optical microscope (POM), and variable temperature small-angle X-ray diffraction (XRD) methods. While essentially all the biphenyl-4,4′-diol- and 4,4′-(diazene-1,2-diyl)- based dimeric derivatives exhibited smectic liquid crystalline mesophases, the nature of which are mesogenic groups dependent, none of the cholesterol- containing compounds and tetramers were mesomorphic. © 2010 Elsevier Ltd. All rights reserved.