Photochemical patterning of a self-assembled monolayer of 7-diazomethylcarbonyl-2,4,9-trithiaadmantane on gold films via wolff rearrangement

Jun Hu, Yubiao Liu, Chalermchai Khemtong, Jouliana M. El Khoury, Timothy J. McAfoos, Ian S. Taschner

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Photolithographic attachment of functional organic molecules via ester or amide linkages to self-assembled monolayers (SAMs) on gold thin films was achieved by employing a novel photoreactive surface anchor, 7- diazomethylcarbonyl-2,4,9-trithiaadmantane. The photoreactive SAM was prepared by the spontaneous physical adsorption of the photoreactive surface anchor onto gold surfaces. The α-diazo ketone moiety of the SAM was found to display the classical Wolff rearrangement reactivity to produce a ketene intermediate on the exposed area. Organic molecules such as alcohols and amines can thus be attached to the gold surfaces selectively by the facile in situ formation of ester or amide linkages. The structure and reactivity of the photoreactive surface anchor were characterized by real-time FT-IR, fluorescence, and polarization modulation infrared reflectance absorption spectroscopy (PM-IRRAS). The Wolff rearrangement reactivity of the SAM suggested that a "surface-isolated" carbonylcarbene may be generated when the SAM was exposed to 255-nm irradiation.

Original languageEnglish (US)
Pages (from-to)4933-4938
Number of pages6
JournalLangmuir
Volume20
Issue number12
DOIs
StatePublished - Jun 8 2004

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Self assembled monolayers
Gold
gold
Anchors
reactivity
Amides
linkages
amides
esters
Esters
modulation
polarization modulation
Molecules
Ketones
Absorption spectroscopy
ketones
Amines
attachment
7-diazomethylcarbonyl-2,4,9-trithiaadamantane
molecules

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Colloid and Surface Chemistry

Cite this

Photochemical patterning of a self-assembled monolayer of 7-diazomethylcarbonyl-2,4,9-trithiaadmantane on gold films via wolff rearrangement. / Hu, Jun; Liu, Yubiao; Khemtong, Chalermchai; El Khoury, Jouliana M.; McAfoos, Timothy J.; Taschner, Ian S.

In: Langmuir, Vol. 20, No. 12, 08.06.2004, p. 4933-4938.

Research output: Contribution to journalArticle

Hu, Jun ; Liu, Yubiao ; Khemtong, Chalermchai ; El Khoury, Jouliana M. ; McAfoos, Timothy J. ; Taschner, Ian S. / Photochemical patterning of a self-assembled monolayer of 7-diazomethylcarbonyl-2,4,9-trithiaadmantane on gold films via wolff rearrangement. In: Langmuir. 2004 ; Vol. 20, No. 12. pp. 4933-4938.
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AU - El Khoury, Jouliana M.

AU - McAfoos, Timothy J.

AU - Taschner, Ian S.

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