ChemInform Abstract: The Self-Assembly of a Lipophilic Deoxyguanosine Derivative and the Formation of a Liquid-Crystalline Phase in Hydrocarbon Solvents.

The lipophilic 3′,5′-di-O-decanoyl-2′-deoxyguanosine (1) in CHCl3 undergoes extensive self-assembly, mediated by H-bonding between the guanine bases, to give ribbon-like aggregates. X-Ray investigation of the platelets obtained from CHCl3 reveals a disordered fibre-like structure consisting of stacks of the ribbon-like aggregates. The aggregates are completely different from the columnar structures, based on G-quartets, which are the building blocks of the mesophases formed by deoxyguanosine oligonucleotides in H2O. In pure hydrocarbons or in CHCl3/hydrocarbons, 1 forms a lyotropic liquid-crystalline phase.