Issue 11, 2011

Click chemistry by microcontact printing on self-assembled monolayers: A structure–reactivity study by fluorescence microscopy

Abstract

Microcontact printing (μCP) has developed into a powerful tool to functionalize surfaces with patterned molecular monolayers. μCP can also be used to induce a chemical reaction between a molecular ink and a self-assembled monolayer (SAM) in the nanoscale confinement between stamp and substrate. In this paper, we investigate the Huisgen 1,3-dipolar cycloaddition, the Diels–Alder cycloaddition and the thiol-ene/yne reaction induced by μCP. A range of fluorescent alkyne inks were printed on azide SAMs and fluorescence microscopy was used to monitor the extent of the 1,3-dipolar cycloaddition on a glass substrate. The rate of cycloaddition depends on the reactivity of the alkyne and on the presence of Cu(I). The cycloaddition is accelerated by Cu(I) but it also proceeds readily in the absence of Cu(I). In addition, a range of fluorescent diene inks were printed on alkene SAMs on glass. In this case, fluorescence microscopy was used to monitor the rate of the Diels–Alder cycloaddition as well as its retro-reaction. Finally, fluorescent thiol inks were printed on alkene SAMs on glass, and fluorescent alkenes and alkynes were printed on thiol SAMs. It is shown that reactions by μCP follow structure–reactivity relationships similar to solution reactions. Under optimized conditions all reactions lead to dense microarrays of addition products within minutes of printing time.

Graphical abstract: Click chemistry by microcontact printing on self-assembled monolayers: A structure–reactivity study by fluorescence microscopy

Supplementary files

Article information

Article type
Paper
Submitted
02 Feb 2011
Accepted
14 Mar 2011
First published
14 Apr 2011

Org. Biomol. Chem., 2011,9, 4108-4115

Click chemistry by microcontact printing on self-assembled monolayers: A structure–reactivity study by fluorescence microscopy

J. Mehlich and B. J. Ravoo, Org. Biomol. Chem., 2011, 9, 4108 DOI: 10.1039/C1OB05187C

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