Functional materials are predicted to have an enormous impact on the field of nanotechnology and these can be expanded by further derivatization of their surfaces on a molecular level to allow for the control of the interactions between material surfaces and their environment. To this end, the cycloaddition chemistry between strained-cyclooctynes and 1,3-dipolar molecules offers a simple, clean, and highly reliable protocol for the modification of material surface functionalities. However, the high reactivity of the strained C-C triple bond of these systems renders the incorporation of these cyclooctyne moieties into materials synthetically challenging or, in some cases, inaccessible. To circumvent this challenge, we seek to employ cyclopropenones as 1) a photo-cage for strained-cyclooctynes to allow for facile incorporation onto material surfaces and 2) a photochemical precursor that, upon decarbonylation, affords the parent strained-alkyne that can be employed in subsequent cycloaddition chemistry. This two-step methodology was applied to the synthesis of photo-clickable Au nanoparticles and norbornene-based polymers. The design, fabrication, and characterization of these materials — Au nanoparticles and polynorbornenes — and their redox-active conjugates will be discussed. Our ability to quantitate surface functionalities and monitor the interfacial chemistry via various spectroscopies (NMR, IR, and UV-Vis) and TGA and TEM will be highlighted. The photoactivated nature of this cycloaddition chemistry will allow for spatial control that will be amenable to the fabrication of nanoelectronic devices. I will also present reflections of my 25+ year relationship with on our Baizer Award winner Professor Flavio Maran.