The power and flexibility of the ring-opening metathesis polymerization (ROMP) method is well-known. This addition polymerization technique is functional-group tolerant, uses stable and well-defined catalysts, and in monomers with plenty of ring strain can be coaxed to proceed in a nearly living manner. For this reason, ROMP is a favorite method for surface-initiated polymerization, second only to hidden-radical polymerization techniques such as ATRP. ROMP-based thin films, prepared by metathesis of catalyst in solution with alkene-functionalized surfaces followed by reaction of immobilized catalyst with monomer in solution, have been used to construct a variety of engineered surfaces. These surfaces include antifouling poly(ethylene oxide) films and self-healing coatings. Surprisingly, although a number of reports exist of the preparation of block copolymers grown from surfaces using SI-ROMP, the present work is the first published example (to our knowledge) of polymers grown using surface-directed ROMP to prepare polymer films or brushes deliberately end-functionalized with small molecules (rather than a second polymer segment in a block copolymerization). Polymer brushes or surface-bound thin films modified specifically with small molecules are interesting for "molecular wire" type applications where we connect an electrically active species -say, an enzyme cofactor, or a photosensitizer -to the surface of an electrode. End-functionalized polymers can also be used to prepare really novel block copolymers by immobilizing the catalyst for a different type of polymerization than the one used to prepare the first chain. By synthesizing norbornene-based ROMP monomers with reactive side chains, we have also prepared functionalizable films where the polymer side chain, rather than the end group, is modified. By incorporating active NHS esters into the sidechain, groups affecting surface energy can be easily incorporated. Formation of intrinsically conducting polymer films can also be approached by incorporating sidechain units that can be converted into a conducting polymer by a second reaction, a technique pioneered in solution by Swager et al. Our monomer is based on Swager's, but with the terminal thiophene units being based on the extremely electron-rich monomer EDOT for easier electropolymerization.