The CuAAC synthesis and the characterization of new rigid nucleobase-decorated tetrapodands exhibiting 1,3,5,7-tetraphenyladamantane and 9,9′-spirobifluorene central units are reported. 1,3,5,7-Tetraphenyladamantane and 3,3′,6,6′-tetrasubstituted 9,9′-spirobifluorene derivatives are tetrahedral building blocks, while the derivatives of 2,2′,7,7′-tetrasubstituted 9,9′-spirobifluorene can lead to 2D architectures.

We describe herein the synthesis and characterization of new rigid nucleobase-decorated tripodands. The synthetic strategy involves the use of new azide functionalized nucleobases (adenine, thymine, and uracil). ES(+)-MS studies of hydrogen-bonding selfassociation as well as associations with complementary nucleosides are also reported.