An unusual self-assembly of a deuteroporphyrin 4-aminothiophenol derivative on Au(111) surfaces

Rudy Martin; Roberto Cao; Franz-Peter Montforts; Paul-Ludwig M. Noeske

doi:10.1039/C3NJ00118K

An unusual self-assembly of a deuteroporphyrin 4-aminothiophenol derivative on Au(111) surfaces

Rudy Martin,^a Roberto Cao,*^a Franz-Peter Montforts*^b and Paul-Ludwig M. Noeske^c

* Corresponding authors

^a Laboratorio de Bioinorgánica, Universidad de La Habana, Zapata y G, Vedado, La Habana, 10400 Cuba
E-mail: caov@fq.uh.cu
Fax: +53-7333502
Tel: +53-78792145

^b Institute of Organic Chemistry, University of Bremen, Leobener Strasse NW 2, Bremen, Germany
E-mail: mont@uni-bremen.de
Fax: +421-218-63120
Tel: +421-218-63120

^c Fraunhofer-Institute for Manufacturing Technology and Applied Materials Research (IFAM), Adhesive Bonding Technology and Surfaces, Wiener Str. 12, Bremen, Germany

Abstract

An unexpected ruthenium(II)-deuteroporphyrin 4-aminothiophenol (4-ATP) thiolester derivative (Ru-4ATPP) was obtained by the condensation of 4-ATP with carbonyl[13,17-bis(propanoic acid)-2,7,12,18-tetramethylporphyrinato]ruthenium(II). Ru-4ATPP was self-assembled on Au(111) surfaces through the terminal amino groups, as shown by cyclic voltammetry (CV) and confirmed by X-ray photoelectron spectroscopy (XPS). A slow and incomplete isomerisation process of the self-assembled 4-RuATPP thiolester to its amido analogue was observed, due to the catalytic effect of the gold surface. Consequently, the formed amido isomer of Ru-4ATPP became self-assembled on Au(111) through the resulting terminal thiolate groups, a condition characterized by CV reductive desorption (peak at ca. −0.7 eV) and XPS (S2p peaks at 162.1 and 163.3 eV).

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Publication details

The article was received on 30 Jan 2013, accepted on 24 Mar 2013 and first published on 25 Mar 2013

Article type: Paper

DOI: 10.1039/C3NJ00118K

Citation: New J. Chem., 2013,37, 1610-1615

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An unusual self-assembly of a deuteroporphyrin 4-aminothiophenol derivative on Au(111) surfaces

R. Martin, R. Cao, F. Montforts and P. M. Noeske, New J. Chem., 2013, 37, 1610
DOI: 10.1039/C3NJ00118K
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New Journal of Chemistry

An unusual self-assembly of a deuteroporphyrin 4-aminothiophenol derivative on Au(111) surfaces

Abstract

Supplementary files

Publication details

An unusual self-assembly of a deuteroporphyrin 4-aminothiophenol derivative on Au(111) surfaces

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