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

Preuss, C.M., Zieger, M.M., Rodriguez-Emmenegger, C., Zydziak, N., Trouillet, V., Goldmann, A.S., & Barner-Kowollik, C. (2014) Fusing catechol-driven surface anchoring with rapid hetero diels-alder ligation. ACS Macro Letters, 3(11), pp. 1169-1173.

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Abstract

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.

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9 citations in Scopus
9 citations in Web of Science®
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ID Code: 99397
Item Type: Journal Article
Refereed: Yes
DOI: 10.1021/mz5006469
ISSN: 2161-1653
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 17 May 2017 00:37

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