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Self-assembled monolayers (SAMs) of C6H5–C≡C–C6H4–C≡C–C6H4SH (1) on Au(111) and Ag(111) exhibit electrical rectifying behavior when probed by the scanning tunneling microscope whereas SAMs derived from decanethiol, benzenethiol and 4-phenylethynylbenzenethiol do not. We suggest that rectification arises from the conjugated length of the molecular framework of 1 and an increase of the donor character of the sulfur atom to this system upon adsorption to the metal. This is supported by surface second-harmonic generation measurements which show a significantly larger second order optical nonlinearity of SAMs of 1 compared to the other systems.
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Dhirani et al. (1997) studied this question.
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