Saccharide-Functionalized Alkanethiols for Fouling-Resistant Self-Assembled Monolayers: Synthesis, Monolayer Properties, and Antifouling Behavior
Saccharide-Functionalized Alkanethiols for Fouling-Resistant Self-Assembled Monolayers: Synthesis, Monolayer Properties, and Antifouling Behavior
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DOI：
10.1021/la202774e
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发表时间：
2011-12-20
期刊：
影响因子：
3.9
通讯作者：
Ederth, Thomas
中科院分区：
文献类型：
--
作者：
Fyrner, Timmy;Lee, Hung-Hsun;Ederth, Thomas
我们描述了一系列的单，二，和三糖官能化的烷硫醇的合成，以及从这些防污自组装单分子膜（SAMs）的形成。使用椭圆偏振法、润湿测量和红外反射吸收光谱法（WAS）表征SAIs、Is。我们表明，碳水化合物部分的结构影响的堆积密度，这也改变了烷烃链的组织。在增加糖部分的大小（从单到二和三糖），单层的结构质量恶化，增加混乱，并为三糖，缓慢的重组动态响应于环境极性的变化进行了观察。这些自组装膜的吸附性能进行了研究，通过从缓冲溶液中的蛋白质吸附实验，以及沉降（附着）测试，使用两种常见的海洋污损物种，游动孢子的绿色macrophage石莼linza和cypris幼虫的藤壶藤壶amphitrite。自组装膜显示出对蛋白质和测试的海洋生物的污染的总体良好的抵抗性。为了提高具有大体积头基的SAM的堆积密度，我们采用混合SAM，其中糖-硫醇用具有小的2-羟乙基头基的填料分子稀释。该方法还提供了一种方法，通过该方法可以改变糖部分的空间可用性，这对于与表面结合的糖的特定相互作用研究是感兴趣的。表面稀释研究的结果和低非特异性吸附到自组装膜上都表明这种方法的可行性。
We describe the synthesis of a series of mono-, di-, and trisaccharide-functionalized alkanethiols as well as the formation of fouling-resistant self-assembled monolayers (SAMs) from these. The SAls,,Is were characterized using ellipsometry, wetting measurements, and infrared reflection absorption spectroscopy (WAS). We show that the structure of the carbohydrate moiety affects the packing density and that this also alters the alkane chain organization. Upon increasing the size of the sugar moieties (from mono- to di- and trisaccharides), the structural qualities of the monolayers deteriorated with increasing disorder, and for the trisaccharide, slow reorganization dynamics in response to changes in the environmental polarity were observed. The antifouling properties of these SAMs were investigated through protein adsorption experiments from buffer solutions as well as settlement (attachment) tests using two common marine fouling species, zoospores of the green macroalga Ulva linza and cypris larvae of the barnacle Balanus amphitrite. The SAMs showed overall good resistance to fouling by both the proteins and the tested marine organisms. To improve the packing density of the SAMs with bulky headgroups, we employed mixed SAMs where the saccharide-thiols are diluted with a filler molecule having a small 2-hydroxyethyl headgroup. This method also provides a means by which the steric availability of sugar moieties can be varied, which is of interest for specific interaction studies with surface-bound sugars. The results of the surface dilution study and the low nonspecific adsorption onto the SAMs both indicate the feasibility of this approach.