Fusing catechol-driven surface anchoring with rapid hetero diels-alder ligation

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. © 2014 American Chemical Society