4.5 Article

Stimuli-Responsive Functionalization Strategies to Spatially and Temporally Control Surface Properties: Michael vs Diels-Alder Type Additions

Journal

JOURNAL OF PHYSICAL CHEMISTRY B
Volume 122, Issue 16, Pages 4481-4490

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.jpcb.8b01652

Keywords

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Funding

  1. DGI [MOTHER MAT2016-80826-R, Dynamo MAT2013-50036EXP, SAF2014-60138-R]
  2. Networking Research Center on Bioengineering, Biomaterials, and Nanomedicine (CIBER-BBN)
  3. Generalitat de Catalunya [2014-SGR-17, 2014-SGR-137]
  4. People Programme (Marie Curie Actions) of the Seventh Framework Programme of the European Union (FP7) under the TECNIOSpring programme [TECSPR15-1-0015]
  5. Agency for Competitiveness and Business of the Government of Catalonia
  6. ACCIO
  7. Max Planck Society through the Max Planck Institute for Medical Research
  8. Max Planck Partner Group Dynamic Biomaterials for Cancer Immunotherapy

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Stimuli-responsive self-assembled monolayers (SAMs) are used to confer switchable physical, chemical, or biological properties to surfaces through the application of external stimuli. To obtain spatially and temporally tunable surfaces, we present microcontact printed SAMs of a hydroquinone molecule that are used as a dynamic interface to immobilize different functional molecules either via Diels-Alder or Michael thiol addition reactions upon the application of a low potential. In spite of the use of such reactions and the potential applicability of the resulting surfaces in different fields ranging from sensing to biomedicine through data storage or cleanup, a direct comparison of the two functionalization strategies on a surface has not yet been performed. Although the Michael thiol addition requires molecules that are commercial or easy to synthesize in comparison with the cyclopentadiene derivatives needed for the Diels-Alder reaction, the latter reaction produces more homogeneous coverages under similar experimental conditions.

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