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From an interplay of high-resolution scanning tunneling microscopy (STM) imaging and density functional theory (DFT) calculations we demonstrate that by delicately choosing the parent molecule (adenine) we are able to tune the self-assembled nanostructures of adenine derivatives which are directed by the specific intermolecular interactions provided by the adenine moiety.

Supramolecular patterns formed by adsorption from a liquid of nucleobase-terminated molecular rods on a graphite surface were investigated by scanning tunneling microscopy.

A series of homo- and heteroditopic thymine- and/or adenine-terminated molecules incorporating rigid aryl or oligo(phenylene ethynylene) linkers has been efficiently synthesized. The key steps involved in the synthesis are the construction of the N-arylated nucleobases using the Chan-Lam-Evans-modified Ullman coupling and their further elaboration using the Sonogashira coupling. Furthermore, the synthesis of a rigid tripodal thymine derivative is reported.