UV-induced tetrazole-thiol reaction for polymer conjugation and surface functionalization
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...
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| Main Authors: | , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
June 8, 2015
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| In: |
Angewandte Chemie. International edition
Year: 2015, Volume: 54, Issue: 30, Pages: 8732-8735 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201502954 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/anie.201502954 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201502954 
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| Author Notes: | Wenqian Feng, Linxian Li, Chengwu Yang, Alexander Welle, Oliver Trapp, and Pavel A. Levkin |
| Summary: | 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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| Item Description: | Gesehen am 03.08.2020 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201502954 |