title: UV-Induced Tetrazole-Thiol Reaction for Polymer Conjugation and Surface Functionalization.
abstract: A UV-induced 1,3-dipolar nucleophilic addition of tetrazoles to thiols is described. Under UV irradiation the reaction proceeds rapidly at room temperature, with high yields, without a catalyst, and in both polar protic and aprotic solvents, including water. This UV-induced tetrazole-thiol reaction was successfully applied for the synthesis of small molecules, protein modification, and rapid and facile polymer-polymer conjugation. The reaction has also been demonstrated for the formation of micropatterns by site-selective surface functionalization. Superhydrophobic-hydrophilic micropatterns were successfully created by sequential modifications of a tetrazole-modified porous polymer surface with hydrophobic and hydrophilic thiols. A biotin-functionalized surface could be fabricated in aqueous solutions under long-wavelength UV irradiation.
authors.affiliation: Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), 76344 Karlsruhe (Germany).|Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, 69120 Heidelberg (Germany).
authors.forename: Wenqian
authors.initials: W
authors.lastname: Feng
authors.affiliation: Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), 76344 Karlsruhe (Germany).|Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, 69120 Heidelberg (Germany).
authors.forename: Linxian
authors.initials: L
authors.lastname: Li
authors.affiliation: Institute of Functional Interfaces (IFG), KIT (Germany).
authors.forename: Chengwu
authors.initials: C
authors.lastname: Yang
authors.affiliation: Institute of Functional Interfaces (IFG), KIT (Germany).|Karlsruhe Nano Micro Facility (KNMF) (Germany).
authors.forename: Alexander
authors.initials: A
authors.lastname: Welle
authors.affiliation: Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, 69120 Heidelberg (Germany).
authors.forename: Oliver
authors.initials: O
authors.lastname: Trapp
authors.affiliation: Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), 76344 Karlsruhe (Germany). levkin@kit.edu.
authors.forename: Pavel A
authors.initials: PA
authors.lastname: Levkin
keywords: nucleophilic addition; photochemistry; polymer conjugation; surface modification; tetrazole-thiol reaction