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Título: | Synthesis of macrocyclic poly(ethylene oxide)s containing a protected thiol group: A strategy for decorating gold surfaces with ring polymers |
Autor: | Aboudzadeh, M. Ali; Dolz, Mikel; Monnier, Xavier; González de San Román, Estíbaliz; Cangialosi, Daniele CSIC ORCID ; Grzelczak, Marek CSIC ORCID ; Barroso-Bujans, Fabienne CSIC ORCID | Fecha de publicación: | 19-nov-2019 | Editor: | Royal Society of Chemistry (UK) | Citación: | Polymer Chemistry 10(47): 6495-6504 (2019) | Resumen: | We introduce an approach to synthesize macrocyclic poly(ethylene oxide)s containing a pendant protected thiol group (pSH-CPEO), which is demonstrated to be able to attach to gold surfaces without prior deprotection. Our strategy is based on a bimolecular approach by which a di-alkyne molecule derived from thiol-protected 3-mercapto-1,2-propanediol and a series of PEO bis(azides) of M = 2, 6, and 11 kg mol are coupled via copper-catalyzed azide-alkyne cycloaddition. The cyclization reaction was verified by size exclusion chromatography and matrix-assisted laser desorption ionization time of flight mass spectrometry. In addition, we used fast scanning calorimetry to evaluate the glass transition temperature (T) of the synthesized pSH-CPEOs. Thanks to the extremely rapid cooling power of this technique, PEO crystallization can be circumvented and, therefore, its fully amorphous state can be investigated. The results confirmed higher T values for macrocycles compared to their chemically equivalent linear precursors. This result highlights the importance of the chain end in affecting the T of polymers. Finally, to demonstrate the ability of pSH-CPEO to covalently attach to gold surfaces, pSH-CPEO samples were allowed to react with gold-coated glass slides and the surface properties were compared with those of the samples obtained by the reaction of linear α-thiol, ω-methoxy PEO (with and without protection of the thiol group) and gold-coated glass slides. X-ray photoelectron spectroscopy data confirmed the formation of Au-S linkages as well as the removal of the thiol protector group through the quantitative analysis of the chemical composition at the surface. The contact angle data of pSH-CPEO/gold exhibited increased hydrophilicity compared to bare gold and topological effects at the interface. A reaction mechanism between the 2,4-dinitrobenzene-protected thiol group and the gold surface is also proposed. | Versión del editor: | http://dx.doi.org/10.1039/c9py01394f | URI: | http://hdl.handle.net/10261/207199 | DOI: | 10.1039/c9py01394f | Identificadores: | doi: 10.1039/c9py01394f e-issn: 1759-9962 issn: 1759-9954 |
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