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Figure S1. Comparison of IR spectra obtained for (a) 2a as a solution in toluene (b) 2b formed via thermolysis in toluene, (c) 3a as a solution in toluene, (d) 3b formed via thermolysis in toluene, (e) 4a as a solution in toluene, (f) 4b formed via thermolysis in toluene. Note that the spectra were taken in transmission mode and have been inverted for easy comparison.

Figure S2. Thermal programmed desorption spectra for (a) 2a (b) 3a and (c) 4a depicting the desorption of the multilayer off of the Pt(111) surface as a function of time.

Figure S3. Comparison of infrared spectra obtained for 2a (a) as a cast film on an NaCl plate, (b) as a solution in CCl4, (c) RAIR spectrum of the multilayer on Pt(111) at 200K in UHV chamber and (c) RAIR spectrum of the monolayer on Pt(111) at 200 K in UHV chamber. Note that spectra (a) and (b) were taken in transmission mode and have been inverted for easy comparison.

Figure S4. Comparison of infrared spectra obtained for 4a (a) as a cast film on an NaCl plate, (b) as a solution in CCl4, (c) RAIR spectrum of the multilayer on Pt(111) at 200 K in UHV chamber and (c) RAIR spectrum of the monolayer on Pt(111) at 200 K in UHV chamber. Note that spectra (a) and (b) were taken in transmission mode and have been inverted for easy comparison.

Figure S5. Comparison of RAIR spectra obtained for (a) 2a as a monolayer on Pt(111), (b) after heating the Pt crystal to 400 K for 60 s, (c) 3a as a monolayer on Pt(111), and (d) after heating the Pt crystal to 400 K for 60 s. All spectra were taken in the UHV chamber at 305 K.

Figure S6. Comparison RAIR spectra of (a) 2b formed via thermolysis of 2a as a monolayer on Pt(111), (b) the monolayer formed after warming up 2b as a multilayer past its desorption temperature, (c) 4b formed via thermolysis of 4a as a monolayer on Pt(111), (d) the monolayer formed after warming up 4b as a multilayer past its desorption temperature.

Figure S7. RAIR spectra of (a) 2a as a saturated monolayer on Pt(111) at 305 K, (b) 2a after being exposed to 254–400 nm UV light for 3 min, (c) 4a as a saturated monolayer on Pt(111) at 305 K and (d) 4a after being exposed to 254–400 nm UV light for 3 min.

Figure S8. RAIR spectra of (a) 2b formed after thermolysis of 2a as a saturated monolayer at 305 K, (b) the resulting spectrum obtained after heating up the Pt crystal to 305 K, (c) 4b formed after thermolysis of 4a as a saturated monolayer at 305 K, and (d) the resulting spectrum obtained after heating up the Pt crystal to 305 K.

Figure S9. RAIR spectra of (a) 2b formed after thermolysis of 2a as a saturated monolayer at 305 K, (b) the resulting spectrum obtained after exposure to methylamine, (c) 4b formed after thermolysis of 4a as a saturated monolayer at 305 K, and (d) the resulting spectrum obtained after exposure to methyl amine.

Scheme S1. Proposed possible oligomerization reaction of methylamine with the pyridyl isocyanate saturated monolayer.

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