As seen in Figure , COT does not react efficiently in ROMP due to the relatively low ring strain of the system. Also, while the conductivity of doped polyacetylene is known to be very high, (10 2 -10 3 Ω -1 cm -1 with iodine doping) it is a relatively unstable material and degrades readily when exposed to air. Since it was apparent from Figure that we would need to continue optimizing the polymerization system to work around the reluctant COT monomer, we chose to approach the problem by redesigning the monomer to both improve ring strain and to incorporate a more stable conjugated repeat unit. We based our approach upon reports of norbornene derivatives in solution which contained electropolymerizable derivatives, and in particular on the work of Swager et al. who prepared a fused norborneneoligoarene monomer and demonstrated its incorporation into block copolymers via ROMP as well as its oxidative polymerization. We chose to modify this design to incorporate the 3,4-ethylenedioxythiophene (EDOT) group, known for its ready electropolymerization and the stability of its doped form. (Scheme 3) While working to polymerize COT from a p-styrenethiol monolayer, we found that this monolayer system was difficult to work with due to its ready thiol-ene self-polymerization reaction. While we were reluctant to give up on this easy-to-synthesize and fully conjugated initiator, we decided to move to a simple terminal alkene monolayer on gold for polymer- There is plenty of detectable EPE material at the surface (Figure ) and the final appearance of a low-potential wave after many cycles as well as the evolution of the formal potential for redox of the EPE sidechain (Figure ) supports our interpretation that the EPE moiety is being crosslinked into a conjugated polymer. In the first cycle, EPE must be oxidized at the monolayer without assistance, requiring a certain voltage of around 1.03. Once this initial stage occurs, EPE is crosslinked near the electrode and this more easily oxidized group provides a "platform" for further oxidative crosslinking, continuing to oxidize EPE moieties deeper in the film in a two-step process. Eventually, single EPE groups are depleted and the largest peak in the film is the doping/dedoping of the fully crosslinked polymer.A similar process is seen in Ocafrain et al. with an EDOT-based monolayer. Unfortunately, attempts at end-functionalization of the growing NbEPE polymer using vinylferrocene did not yield any measurable surface-bound ferrocene by cyclic voltammetry. We attribute both the failure of end-functionalization and the relatively low thickness of the polyNbEPE brush to chain termination in the polymerization. We and others have shown that surface-initiated ROMP is negatively impacted by the presence of large, bulky substituents on the monomer. This effect appears to be particularly strong in the case of symmetrically substituted norbornene derivatives with bulky groups at the 2 and 3 positions. We speculate that in order to produce a viable system for the preparation of end-functionalized brushes using the tandem ROMP/electropolymerization strategy, it will be necessary to modify the structure of the monomer to incorporate a less sterically demanding group as the oxidatively polymerizable side chain. The need for a relatively large conjugated aryl system for easy oxidative polymerization is in conflict with the demands of the SI-ROMP system, which works best with sterically unhindered monomers. Some balance will need to be struck between the requirements of these two polymerization methods in the tandem system to find a monomer that will react cleanly in SI-ROMP to produce a uniform film with active endgroups but also oxidatively polymerize to give conductive films. The Sotzing group has reported one potential SI-ROMP-based electropolymerizable monomer, which similarly to our own system contains EDOT units but which has a CH 2 O spacer between the norbornene moiety and the central aryl group. This system gives thicker films than our NbEPE monomer with a rough morphology and features up to 35 nm in height. Based on our pCOT results, the promising Sotzing BEDOT-T monomer should be screened in an end-functionalization experiment, as it seems to give thicker films of comparable roughness and may end-functionalize well.