Synthesis and Self-Assembly of Alternating Heterodinucleoside Polytriazoles

In recent years, the synthesis and self-assembly studies of artificial nucleic acids have drawn tremendous scientific attention and interest. In this manuscript, we report a strategy for synthesizing double-stranded alternating heterodinucleoside polytriazoles through the 1,4-regioregular copper(I)-catalyzed [3+2] azide-alkyne cycloaddition polymerization of the complementary hydrogen-bonded, sequence-embedded, azide/alkyne-functionalized heterodinucleoside monomeric complexes. The distinct self-assembly behaviors between the heterodinucleoside polytriazoles and their monomeric precursors indicate that the 1,4-regioregular polytriazole backbone can not only constrain and regularize the complementary hydrogen bonds of the nucleobases but also transfer the molecular chirality of monomers into the supramolecular assemblies to induce the formation of helical nanofibers. We believe that this approach can be further extended to the iterative polymerization of nucleoside monomers with more complex nucleobase sequences for developing novel artificial nucleic acids.