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N-Heterocyclic carbenes (NHCs) were functionalized with a triisopropylsilyl (TIPS)-protected alkyne group and self-assembled on Au films to enable post-deposition functionalization by C-C coupling reactions. The TIPS group efficiently protected the alkyne and prevented its deprotonation during surface-anchoring of NHC. Sonogashira C-C coupling reactions were performed on the Au film in high yield following removal of the TIPS group, demonstrating that post-deposition coupling reactions can be employed to widen the chemical s