This seminar will feature an overview of research conducted by an undergraduate research group. Work toward novel organometallic cyclophanes and metal-mediated supramolecular self-assemblies will be described, including a serendipitous reaction that motivated development of methods for desilylative Sonogashira cross coupling and desilylative 1,2,3-triazole synthesis. In turn, our 1,2,3-triazole research has motivated prospecting efforts towards a novel atropisomeric bis-1,2,3-triazole scaffold and towards 1,2,3-triazole-derived fluorophores and selective colorimetric sensors.