Adding Spatial Control to Click Chemistry: Phototriggered Diels–Alder Surface (Bio)functionalization at Ambient Temperature

Authors

  • Thomas Pauloehrl,

    1. Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie and Centre for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76128 Karlsruhe (Germany) http://www.macroarc.de
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  • Dr. Guillaume Delaittre,

    1. Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie and Centre for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76128 Karlsruhe (Germany) http://www.macroarc.de
    2. Zoologisches Institut, Zell- und Neurobiologie and Centre for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), 76131 Karlsruhe (Germany)
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  • Volker Winkler,

    1. Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie and Centre for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76128 Karlsruhe (Germany) http://www.macroarc.de
    2. Institute for Applied Materials (IAM-WPT), Karlsruhe Institute of Technology (KIT), 76344 Eggenstein-Leopoldshafen (Germany)
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  • Dr. Alexander Welle,

    1. Institute for Biological Interfaces (IBG I), Karlsruhe Institute of Technology (KIT), 76344 Eggenstein-Leopoldshafen (Germany)
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  • Dr. Michael Bruns,

    1. Institute for Applied Materials (IAM-WPT), Karlsruhe Institute of Technology (KIT), 76344 Eggenstein-Leopoldshafen (Germany)
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  • Prof. Dr. Hans G. Börner,

    1. Laboratory for Organic Synthesis of Functional Systems, Department of Chemistry, Humboldt-Universität zu Berlin, 12489 Berlin (Germany)
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  • Dr. Alexandra M. Greiner,

    1. Zoologisches Institut, Zell- und Neurobiologie and Centre for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), 76131 Karlsruhe (Germany)
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  • Prof. Dr. Martin Bastmeyer,

    1. Zoologisches Institut, Zell- und Neurobiologie and Centre for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), 76131 Karlsruhe (Germany)
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  • Prof. Dr. Christopher Barner-Kowollik

    Corresponding author
    1. Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie and Centre for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76128 Karlsruhe (Germany) http://www.macroarc.de
    • Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie and Centre for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76128 Karlsruhe (Germany) http://www.macroarc.de
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  • C.B.K. acknowledges continued funding from the Karlsruhe Institute of Technology (KIT), the German Research Council (DFG), and the Ministry of Science and Arts of the state of Baden-Württemberg supporting the current project. T.P.’s PhD studies are funded by the Fonds der Chemischen Industrie. G.D. thanks the Alexander von Humboldt Foundation for financial support via a Humboldt Research Fellowship for Postdoctoral Researchers. The authors are indebted to Dr. T. Gruendling, K. Oehlenschlaeger, and M. Glassner for their initial studies on o-quinodimethanes.

Abstract

original image

A photoconjugation strategy based on light-triggered Diels–Alder addition of o-quinodimethanes is compatible with biomolecules and proceeds rapidly at ambient temperature without the need of a catalyst. Spatial control was confirmed by photopatterning of a small-molecule ATRP initiator, a polymer, and a peptide in a time-of-flight secondary-ion mass spectrometry investigation.

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