Tailoring the Hydrophilic/Lipophilic Balance of Clickable Mesoporous Organosilicas by the Copper-Catalyzed Azide鈥揂lkyne Cycloaddition Click-Functionalization

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• 作者：Achraf Noureddine ; Philippe Trens ; Guillaume Toquer ; Xavier Catto毛n ; Michel Wong Chi Man
• 刊名：Langmuir
• 出版年：2014
• 出版时间：October 21, 2014
• 年：2014
• 卷：30
• 期：41
• 页码：12297-12305
• 全文大小：622K
• ISSN：1520-5827

文摘

We have designed and synthesized a clickable bridged silsesquioxane material featuring pendant alkyne chains as an aggregate of golf-ball-like nanoparticles, as evidenced by scanning electron microscopy (SEM), transmission electron microscopy (TEM), and small- and wide-angle X-ray scattering (SWAXS). Using the copper-catalyzed azide鈥揳lkyne cycloaddition reaction with a range of organic azides of variable characteristics, we transformed this parent bridged silsesquioxane into new materials with tunable hydrophilic/lipophilic balance in high conversions while preserving the original morphology. N₂, cyclohexane, and water sorption experiments were used to quantify the affinity of these materials toward the sorbates through the determination of their Henry鈥檚 constants. This resulted in the following hydrophilic scale: M-OH > M-PEG > M-C6 > M-Ph > M-F > M-C16, which was mostly confirmed by SWAXS measurements.