Using benzophenone (BP) as a photochemical cross-linker allows for a truly versatile approach to create surfaces with various practical functionalities. The use of BP pendent groups offers a wide range of possibilities to design polymers with a variety of chemical functional groups and/or combine with delicate nano- or micro- structures to achieve specialized interfacial properties of substrates. Herein, a series of antimicrobial small molecules and polymers were prepared and successfully grafted to surfaces trigger by mild UV irradiation. The biocidal components of such materials utilizes long alkyl chain substituted poly quaternary ammoniums (PQA). The kinetics of the photo-cross-linking of BP containing PQA were studied using UV-vis spectroscopy and high efficiency of BP-activated surface grafting was realized. Covalently functionalized surfaces were afforded with excellent antimicrobial activity on contact with Staphylococcus aureus and Escherichia coli in a non-leaching fashion. In addition, one of the hypothesized antibacterial mechanism of surface bound PQA, phospholipid sponge effect, was verified using BP/dodecyl pendent quaternary polyethyleneimine (PEI) films. The action of anionic lipid abstraction by porous PQA was confirmed by studying the swelling behavior of the polymer films with gradient cross-linking density exposed to anionic and neutral lipid solutions. This hypothesis was further supported by the fact that the antibacterial efficacy of PQA films gradually reduced with increase in cross-linking density. An approach to enhance the antimicrobial activity of biocompatible polymers were established by combing BP-based PQA coating with embedded nitrous oxide releasing agent. Functionalized CarboSil prepared via this method showed higher antibacterial efficacy compared to either antibacterial agent alone towards two major bacteria involved in urinary track infections, Staphylococcus aureus and Pseudomonas aeruginosa. Another functionality, anti-icing, was immobilized on glass and plastic surfaces using a BP pendent fluorinated copolymer that were prepared using free radical polymerization. In order to maximize the surface roughness which is critical to icephobic coatings, silica nanoparticles were dispersed within the polymer matrix to generate a hierarchical topography. The nanocomposites functionalized surfaces successfully prevent ice formation upon impinging of supercooled water. Finally, by studying the commoner effect on the mechanical durability of the BP pendent polymers, the robustness of the surface- grafted composites was improved, providing guidelines to design rapid and durable coatings using BP photo-cross-linker.