mdh.sePublications
Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Novel method for preparation of disulfides on silicon
Mälardalen University, School of Sustainable Development of Society and Technology.
Mälardalen University, School of Sustainable Development of Society and Technology.
Uppsala University, Sweden.
Uppsala University, Sweden.
Show others and affiliations
2001 (English)In: Langmuir, ISSN 0743-7463, Vol. 17, no 2, p. 6056-6058Article in journal (Refereed) Published
Abstract [en]

This work describes an efficient novel method to incorporate reactive disulfide bonds onto a silica surface under mild reaction conditions. The reactive thiol groups introduced onto the silicon surface in the first reaction step will be oxidized but easily converted into highly reactive thiopyridyl groups, which can therefore easily be utilized for further organic synthesis involving thiol-containing molecules. This is done in a way that yields approximately a monolayer of reactant on the surface, thereby not adding to the roughness of the surface, of special importance, for instance, for single molecule interaction studies.

Place, publisher, year, edition, pages
2001. Vol. 17, no 2, p. 6056-6058
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:mdh:diva-4161DOI: 10.1021/la0155092ISI: 000171305700008Scopus ID: 2-s2.0-0035797975OAI: oai:DiVA.org:mdh-4161DiVA, id: diva2:121035
Available from: 2008-02-06 Created: 2008-02-06 Last updated: 2015-07-08Bibliographically approved
In thesis
1. Heterogenization of a Cobalt Porphyrin Catalyst Investigated by Scanning Probe Microscopy and X-Ray Photoelectron Spectroscopy: The Effect on Catalysis of Oxidation Reactions
Open this publication in new window or tab >>Heterogenization of a Cobalt Porphyrin Catalyst Investigated by Scanning Probe Microscopy and X-Ray Photoelectron Spectroscopy: The Effect on Catalysis of Oxidation Reactions
2008 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

Construction of advanced materials through self-assembly on the molecular level is an important route to achieve novel functionality. Self-assembly of thiols onto gold has during the last decades shown greate promise in the creation of functional nanomaterials, such as sensors or catalysts, but for many applications silicon should be a better substrate since it offers semiconducting properties and better processing abilities in addition to being cheaper. This work describes an efficient novel method to incorporate reactive disulfide bonds onto a silica surface under mild reaction conditions. The reactive thiol groups introduced onto the silica surface will be oxidized but is then converted into highly reactive thiopyridyl groups, which can easily be utilized for further organic synthesis involving thiol-containing molecules.

Cobalt tetraarylporphyrins with thioacetate-functionalized carbon chains on the aryl groups were synthesized (CoTPP-L) and were used as a model system for investigating catalytic activity in homogeneous and heterogeneous oxidation catalysis. For heterogeneous catalysis CoTPP-L was immobilized onto gold surfaces through thiol-gold self-assembly, and onto silica surfaces by the above mentioned disulfide exchange method.

The properties of the molecular layers were characterized on the molecular level by means of X-ray photoelectron spectroscopy (XPS) and scanning probe microscopy (SPM). The immobilization on gold surfaces took place through the formation of multiple thiolate bonds and it could be controlled by varying the preparation scheme. More thiolate bonds form if the thioacetyl protective groups of the thiol linkers are cleaved off prior to immobilization. The CoTPP-L molecules were in all cases found to form stable disordered monolayers on gold surfaces. On silica surfaces the CoTPP-L forms patchwise multilayers.

The catalytic performance of the heterogenized systems (CoTPP-L immobilized onto gold or silicon wafers) was evaluated and it was found that the strong inactivation observed for their homogeneous congener was avoided. As a result, the turnover number per molecule in heterogeneous catalysis was at least 100 times higher than that of the corresponding homogeneous catalyst. It is thus demonstrated that the performance of these catalysts can be dramatically improved if the catalyst arrangement can be controlled on the molecular level. Work is ongoing to extend the system to high surface area materials.

Place, publisher, year, edition, pages
Akademin för hållbar samhälls- och teknikutveckling, 2008
Series
Mälardalen University Press Dissertations, ISSN 1651-4238 ; 57
National Category
Other Chemical Engineering
Research subject
Bioteknik/kemiteknik
Identifiers
urn:nbn:se:mdh:diva-492 (URN)978-91-85485-71-0 (ISBN)
Public defence
2008-03-07, Filen, Verktyget, Smedjegatan 37, Eskilstuna, 10:00
Opponent
Supervisors
Available from: 2008-02-06 Created: 2008-02-06

Open Access in DiVA

No full text in DiVA

Other links

Publisher's full textScopus

Search in DiVA

By author/editor
Quist, A.P.Oscarsson, S.
By organisation
School of Sustainable Development of Society and Technology
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 76 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf