Triethynylmethanol Derivatives: Stable Acetylenic Building Blocks for Surface Chemistry

The synthesis of non-conjugated, carbon-rich building blocks is described, based on a basic scaffold of triethynylmethanol (TEtM). The substitution of the ethynyl groups can be easily varied (including R3Si, H, Br), and this allows structural tuning for stabilization, synthetic derivatization, and adsorption on Ag(111) or Au(111). X-ray crystallography helps to explain the surprising stability of the selected derivatives in the solid state, and an unusual form of hydrogen bonding is identified from these analyses. Preliminary efforts to achieve surface-based reactions on Ag(111) and Au(111) are outlined experimentally and computationally.