Direct UV-induced functionalization of surface hydroxy groups by thiol-ol chemistry

Linxian Li; Junsheng Li; Xin Du; Alexander Welle; Michael Grunze; Oliver Trapp; Pavel A Levkin

doi:10.1002/anie.201310692

Direct UV-induced functionalization of surface hydroxy groups by thiol-ol chemistry

Angew Chem Int Ed Engl. 2014 Apr 7;53(15):3835-9. doi: 10.1002/anie.201310692. Epub 2014 Mar 5.

Authors

Linxian Li¹, Junsheng Li, Xin Du, Alexander Welle, Michael Grunze, Oliver Trapp, Pavel A Levkin

Affiliation

¹ Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), 76344 Karlsruhe (Germany); Department of Organic Chemistry, University of Heidelberg (Germany).

PMID: 24595963
DOI: 10.1002/anie.201310692

Abstract

A novel UV-initiated surface modification method for the direct functionalization of surface hydroxy groups with thiol-containing molecules (termed "thiol-ol" modification) is described. This method is based on the oxidative conjugation of thiols to hydroxy groups. We demonstrate that different thiol-containing molecules, such as fluorophores, thiol-terminated poly(ethylene glycol) (PEG-SH), and a cysteine-containing peptide, can be attached onto the surface of porous poly(2-hydroxyethyl methacrylate-co-ethylene dimethacrylate). Direct functionalization of other hydroxy-group-bearing surfaces, fabrication of micropatterns, and double patterning have been also demonstrated using the thiol-ol method.

Keywords: alcohols; photochemistry; photopatterning; surface chemistry; thiols.