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A Short-Chain Multibranched Perfluoroalkyl Thiol for More Sustainable Hydrophobic Coatings
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2018-07-16 00:00:00 , DOI: 10.1021/acssuschemeng.8b00777 Valentina Dichiarante 1 , Maria I. Martinez Espinoza 1 , Lara Gazzera 1 , Maja Vuckovac , Mika Latikka , Gabriella Cavallo 1 , Giuseppina Raffaini 1 , Reinier Oropesa-Nuñez 2 , Claudio Canale 2, 3 , Silvia Dante 2 , Sergio Marras 2 , Riccardo Carzino 2 , Mirko Prato 2 , Robin H. A. Ras 4 , Pierangelo Metrangolo 1
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2018-07-16 00:00:00 , DOI: 10.1021/acssuschemeng.8b00777 Valentina Dichiarante 1 , Maria I. Martinez Espinoza 1 , Lara Gazzera 1 , Maja Vuckovac , Mika Latikka , Gabriella Cavallo 1 , Giuseppina Raffaini 1 , Reinier Oropesa-Nuñez 2 , Claudio Canale 2, 3 , Silvia Dante 2 , Sergio Marras 2 , Riccardo Carzino 2 , Mirko Prato 2 , Robin H. A. Ras 4 , Pierangelo Metrangolo 1
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Perfluorocarbons (PFCs) have proven to be very efficient in building up omniphobic surfaces because of the peculiar properties of fluorine atoms. However, due to their environmental impact and bioaccumulative potential, perfluorinated surfactants with chains longer than six carbon atoms have been banned, and other alternatives had to be found. Herein, we demonstrate the possibility to build omniphobic self-assembled monolayers (SAMs) using a multibranched fluorinated thiol (BRFT) bearing ultrashort fluorinated alkyl groups, surrounding a hydrocarbon polar core. This unique design allows us to multiply the number of fluorine atoms in the molecule (27 F atoms per molecule), affording a high fluorine density on the surface and a low surface free energy. Moreover, the presence of four ether bonds in the core may hasten molecular degradation in the environment because of the cleavage of such bonds in physiological conditions, thus overcoming bioaccumulation issues. BRFT may effectively represent a valuable substitute of long-chain perfluoroalkyl thiols. In fact, BRFT SAMs show the same hydrophobic and oleophobic performances of standard linear perfluoroalkyl thiols (such as 1H,1H,2H,2H-perfluorodecanethiol, PFDT), giving rise to more stable surfaces with a better frictional behavior. Superhydrophobicity was also observed with SAMs grown on nanostructured Cu/Ag surfaces. Our results have proven the ability of short-chain multibranched fluorous molecules to behave as suitable replacements for long-chain perfluoroalkanes in the field of surface coatings. Our molecules may be applied to various surfaces because of the available multiple choice of linker chemistry.
中文翻译：
短链多支链全氟烷基硫醇，用于更可持续的疏水涂料
由于氟原子的独特特性，全氟化碳（PFC）已被证明非常有效地建立了疏油性表面。然而，由于其对环境的影响和生物蓄积潜力，链长于六个碳原子的全氟表面活性剂已被禁止，必须寻找其他替代方法。在本文中，我们证明了使用带有超短氟化烷基的多支链氟化硫醇（BRFT）围绕烃极性核构建全疏自组装单分子膜（SAMs）的可能性。这种独特的设计使我们能够增加分子中氟原子的数量（每个分子27 F个原子），从而在表面上提供高的氟密度，并提供低的表面自由能。而且，核心中四个醚键的存在可能会由于环境条件下此类键的断裂而加速环境中的分子降解，从而克服了生物蓄积问题。BRFT可以有效代表长链全氟烷基硫醇的宝贵替代品。实际上，BRFT SAMs具有与标准线性全氟烷基硫醇（例如1H，1H，2H，2H-全氟癸烷硫醇（PFDT））相同的疏水性和疏油性，可产生更稳定的表面并具有更好的摩擦性能。在纳米结构的Cu / Ag表面上生长的SAM也观察到超疏水性。我们的结果证明了短链多支氟分子在表面涂料领域中能够替代长链全氟烷烃的能力。
更新日期：2018-07-16
中文翻译：
短链多支链全氟烷基硫醇，用于更可持续的疏水涂料
由于氟原子的独特特性，全氟化碳（PFC）已被证明非常有效地建立了疏油性表面。然而，由于其对环境的影响和生物蓄积潜力，链长于六个碳原子的全氟表面活性剂已被禁止，必须寻找其他替代方法。在本文中，我们证明了使用带有超短氟化烷基的多支链氟化硫醇（BRFT）围绕烃极性核构建全疏自组装单分子膜（SAMs）的可能性。这种独特的设计使我们能够增加分子中氟原子的数量（每个分子27 F个原子），从而在表面上提供高的氟密度，并提供低的表面自由能。而且，核心中四个醚键的存在可能会由于环境条件下此类键的断裂而加速环境中的分子降解，从而克服了生物蓄积问题。BRFT可以有效代表长链全氟烷基硫醇的宝贵替代品。实际上，BRFT SAMs具有与标准线性全氟烷基硫醇（例如1H，1H，2H，2H-全氟癸烷硫醇（PFDT））相同的疏水性和疏油性，可产生更稳定的表面并具有更好的摩擦性能。在纳米结构的Cu / Ag表面上生长的SAM也观察到超疏水性。我们的结果证明了短链多支氟分子在表面涂料领域中能够替代长链全氟烷烃的能力。
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