Self-assembled monolayers and multilayers of conjugated thiols, α,ω-dithiols, and thioacetyl-containing adsorbates. Understanding attachments between potential molecular wires and gold surfaces

James M. Tour, LeRoy Jones, Darren L. Pearson, Jaydeep J S Lamba, Timothy P. Burgin, George M. Whitesides, David L. Allara, Atul N. Parikh, Sundar V. Atre

Research output: Contribution to journalArticle

691 Scopus citations

Abstract

This paper describes studies of the formation of self-assembled monolayers (SAMs) and multilayers on gold surfaces of rigid-rod conjugated oligomers that have thiol, α,ω-dithiol, thioacetyl, or α,ω-dithioacetyl end groups. The SAMs were analyzed using ellipsometry, X-ray photoelectron spectroscopy (XPS), and infrared external reflectance spectroscopy. The thiol moieties usually dominate adsorption on the gold sites; interactions with the conjugated π-systems are weaker. Rigid rod α,ω-dithiols form assemblies in which one thiol group binds to the surface while the second thiol moiety projects upward at the exposed surface of the SAM. In situ deprotection of the thiol moieties by deacylation of thioacetyl groups using NH4OH permits formation of SAMs without having to isolate the oxidatively unstable free thiols. Moreover, direct adsorption, without exogenous base, of the thioacetyl-terminated oligomers can be accomplished to generate gold surface-bound thiolates. However, in the non-base-promoted adsorptions, higher concentrations of the thioacetyl groups, relative to that of thiol groups, are required to achieve monolayer coverage in a given interval. A thiol-terminated phenylene-ethynylene system was shown to have a tilt angle of the long molecular axis of <20° from the normal to the substrate surface. These aromatic α,ω-dithiol-derived monolayers provide the basis for studies leading to the design of molecular wires capable of bridging proximate gold surfaces.

Original languageEnglish (US)
Pages (from-to)9529-9534
Number of pages6
JournalJournal of the American Chemical Society
Volume117
Issue number37
StatePublished - Sep 20 1995
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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    Tour, J. M., Jones, L., Pearson, D. L., Lamba, J. J. S., Burgin, T. P., Whitesides, G. M., Allara, D. L., Parikh, A. N., & Atre, S. V. (1995). Self-assembled monolayers and multilayers of conjugated thiols, α,ω-dithiols, and thioacetyl-containing adsorbates. Understanding attachments between potential molecular wires and gold surfaces. Journal of the American Chemical Society, 117(37), 9529-9534.