Fusing Catechol-Driven Surface Anchoring with Rapid Hetero Diels–Alder Ligation

• Published in: ACS macro letters Vol. 3; no. 11; pp. 1169 - 1173
• Main Authors: Preuss, Corinna M, Zieger, Markus M, Rodriguez-Emmenegger, Cesar, Zydziak, Nicolas, Trouillet, Vanessa, Goldmann, Anja S, Barner-Kowollik, Christopher
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 18-11-2014
• ISSN: 2161-1653; 2161-1653
• DOI: 10.1021/mz5006469

We fuse the surface anchoring abilities of catechols with the rapid ligating nature of thiocarbonyl thio-based hetero-Diels–Alder (HDA) reactions via the synthesis of a new small molecule (HDA-DOPA-Cp) combining a HDA moiety with a catechol. Inspired by the mechanism of strong adhesion of marine mussels, we employed catechols as anchors to attach HDA ligation points to silicon wafers. The latter was exploited to generate a base for the HDA reactions on the surface employing α-cyclopentadiene (Cp) functional polymers such as poly(ethylene glycol)-Cp (PEG-Cp) and poly(trifluoro ethyl methacrylate)-Cp (PTFEMA-Cp) as dienes. By utilizing the fast and efficient HDA chemistry in combination with catechol anchoring groups, a new method for creating functional surfaces was developed.