The self-assembly of a lipophilic guanosine nucleoside into polymeric columnar aggregates: The nucleoside structure contains sufficient information to drive the process towards a strikingly regular polymer
E. Mezzina et al., The self-assembly of a lipophilic guanosine nucleoside into polymeric columnar aggregates: The nucleoside structure contains sufficient information to drive the process towards a strikingly regular polymer, CHEM-EUR J, 7(2), 2001, pp. 388-395
Lipophilic guanosine derivatives act as self-assembled ionophores. In the p
resence of alkali metal ions in organic solvents, these G derivatives can f
orm tubular polymeric structures. The molecular aggregates formed by 3',5'-
didecanoyl-2'-deoxyguanosine (1) have been characterised by SANS and NMR sp
ectroscopy. The polymer is structured as a pile of stacked G quartets held
together by the alkali metal ions that occupy the column's central channel.
The deoxyribose moieties, with their alkyl substituents, surround the stac
ked G quartets. and the nucleoside's long-chain alkyl tails are in intimate
contact With the organic solvent. In this polymeric structure, there is an
amazing regularity in the rotamers around the glycosidic bond within each
C quartet and in the repeat sequence of the G quartets along the columns. I
n hydrocarbon solvents, these columnar aggregates form lyomesophases of the
cholesteric and hexagonal types.