Non-symmetric dimesogens are composed of two different mesogenic units link
ed via a flexible spacer. In this study, a new type of non-symmetric dimeso
gen has been built through the self-assembly via intermolecular hydrogen bo
nding between appropriately designed H-bond donor (3-cholesteryloxycarbonyl
pentanoic acid) and acceptor (aromatic mesogen with a pyridyl group) moieti
es. As for covalently linked dimesogens, several types of smectic periodici
ties are observed for these H-bonded cholesteryl compounds depending on the
length of the terminal chain of the acceptor moiety: a smectic periodicity
resulting from associated dimesogens is observed for long terminal chains,
while short chain homologues display an intercalated structure correspondi
ng to half the molecular length. The competition between these two incommen
surate lengths can induce an incommensurate smectic phase where the two sme
ctic periodicities coexist at long range.