Molecular layers on nanoporous gold surfaces were formed from terminal phenyl alkynes with varying distal functionalities. The resulting surfaces were characterized using X-ray photoelectron spectroscopy, cyclic voltammetry, electrochemical impedance spectroscopy, and infrared reflection absorption spectroscopy. X-ray photoelectron spectroscopy showed that phenyl alkynes with a wide variety of distal groups formed molecular layers, but the resulting molecular layers did not have dense binding density compared to a thiol-based analogue. Hammett studies of the linear free energy relationship between the binding density and the Hammett electronic parameters indicated a mechanism in which a proton is lost and negative charge is present on the alkyne. Electrochemical measurements demonstrated that the molecular layers have high stability and electrochemical transmissivity compared to thiol-based analogues. Impedance spectroscopy fit to a modified Randles equivalent circuit was consistent with molecular layers that were transmissive and did not densely cover the surface. These findings extend the scope of molecular structures that can be successfully used for alkyne-based attachments and provide mechanistic insight through the study of electron-donating and -withdrawing substituents.
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