UV‐Induced Tetrazole‐Thiol Reaction for Polymer Conjugation and Surface Functionalization |
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| Authors: | Wenqian Feng Dr. Linxian Li Chengwu Yang Dr. Alexander Welle Prof. Dr. Oliver Trapp Dr. Pavel A. Levkin |
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| Affiliation: | 1. Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), 76344 Karlsruhe (Germany);2. Organisch‐Chemisches Institut, Ruprecht‐Karls‐Universit?t Heidelberg, 69120 Heidelberg (Germany);3. Institute of Functional Interfaces (IFG), KIT (Germany);4. Karlsruhe Nano Micro Facility (KNMF) (Germany) |
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| 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. |
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| Keywords: | nucleophilic addition photochemistry polymer conjugation surface modification tetrazole‐thiol reaction |
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