**3. Conclusions**

The solid-state packing behavior of tetrakis(4-((trimethylsilyl)ethynyl)phenyl)methane [**TMS4TEPM**] and 1,3,5,7-tetrakis(4-((trimethylsilyl)ethynyl)phenyl)adamantane [**TMS4TEPA**] showed some degree of extrinsic porosity. These two molecules were converted into tecton-like derivatives with XB capability, **I4TEPM** and **I4TEPA**, in order to investigate the power of iodoethynyl recognition sites in the context of solid-state packing and extrinsic porosity. Our results demonstrate that, even though **I4TEPA** tends not to form crystalline unary or binary solids, **I4TEPM** crystallizes into porous solids in its neat form as well as with suitable co-formers. The binary systems formed with coordinating solvents (i.e.,**I4TEPM**·4Pyridine,**I4TEPM**·2THF,**I4TEPM**·2DMSO and **I4TEPM**·2Dioxane) are prone to collapse upon solvent removal. It is therefore rational to think that **I4TEPM** would offer more stable crystals if the co-formers employed are solids at ambient conditions. Efforts to explore these new possibilities, especially utilizing molecules with tetrahedrally-disposed XB accepting sites (e.g., tetraazaadamantane, tetrakis(4-pyridyl)cyclobutane, tetrakis(4-pyridyloxymethyl)methane) are currently being undertaken in our lab.
