This work presents a rare example of end-functionalization of a conducting polymer brush grown from a surface, as well as the first report of an end-functionalized polymer brush grown via ROMP. A doped polyacetylene film on gold terminated in ferrocene groups gives reasonably rapid (2-3 s -1 ) rate constants for the ferrocene redox reaction. While neither the surface coverage achieved using vinylferrocene nor the electron transfer rate of the system are as high as conjugated monolayers, the results are promising for a proof-of-concept study and after optimization, the techniques we describe may find use in construction of molecular junctions. We have synthesized a a fused norbornene/teraryl EDOT-bearing monomer Nb-EPE and prepared an oxidatively polymerizable surface-initiated polymer film, poly-NbEPE, using a SI-ROMP procedure on Nb-EPE. This film system is not promising for molecular wire applications, as it displays no measurable end-functionalization with vinylferrocene and monosubstituted norbornene derivatives seem to be inherently easier to polymerize in the sterically demanding surface environment. However, this highly electroactive monomer may be useful for solution polymerizations. We have also reported a convenient synthesis using thionyl chloride of the now-commercially available norbornene active ester monomer Nb-NHS, and shown that it polymerizes in a SI-ROMP reaction to give films up to 45 nm in thickness which can be readily reacted with an amine to modify the sidechain. This technique may be a useful tool in surface modification using SI-ROMP. Exploration of ROMP-based techniques as a means to produce "molecular wire" architectures would rapidly become more practical if conditions for high-efficiency end-functionalization of growing conjugated polymer chains can be realized, either by optimization of any of the proof-of-concept techniques described in this report or by other methods.