Rationalising Supramolecular Hydrogelation of Bis-Urea-Based Gelators through a Multiscale Approach.,ChemPlusChem

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Rationalising Supramolecular Hydrogelation of Bis-Urea-Based Gelators through a Multiscale Approach.
ChemPlusChem ( IF 3.0 ) Pub Date : 2019-11-22 , DOI: 10.1002/cplu.201900551
Ruben Van Lommel _{1,

2} , Laurens A J Rutgeerts ₂ , Wim M De Borggraeve ₂ , Frank De Proft ₁ , Mercedes Alonso ₁

Affiliation

The current approach to designing low-molecular-weight gelators relies on a laborious trial-and-error process, mainly because of the lack of an accurate description of the noncovalent interactions crucial for supramolecular gelation. In this work, we report a multiscale bottom-up approach composed of several computational techniques to unravel the key interactions in a library of synthesized bis-urea-based gelators and rationalize their experimentally observed hydrogelation performance. In addition to density functional theory calculations and molecular dynamics, the noncovalent interaction index is applied as a tool to visualise and identify the different types of noncovalent interactions. Interestingly, as well as hydrogen bonds between urea moieties, hydrogen bonds between a urea moiety and a pyridine ring were shown to play a detrimental role in the early aggregation phase. These findings enabled us to explain the hydrogelation performance observed in a library of twelve bis-urea derivatives, which were synthesized with 58-95 % yields. From this library, three compounds were discovered to effectively gel water, with the most efficient hydrogelator only requiring a concentration of 0.2 w/v%.

中文翻译：

通过多尺度方法合理化双脲基胶凝剂的超分子水凝胶化。

设计低分子量胶凝剂的当前方法依赖于费力的反复试验过程，这主要是因为缺乏对超分子胶凝至关重要的非共价相互作用的准确描述。在这项工作中，我们报告了一种由多种计算技术组成的多尺度自下而上的方法，以阐明合成的基于双脲的胶凝剂库中的关键相互作用，并使它们在实验中观察到的水凝胶化性能合理化。除了密度泛函理论计算和分子动力学以外，非共价相互作用指数还用作可视化和识别不同类型的非共价相互作用的工具。有趣的是，以及尿素部分之间的氢键已显示尿素部分和吡啶环之间的氢键在早期聚集阶段起有害作用。这些发现使我们能够解释在十二种双脲衍生物的文库中观察到的水凝胶化性能，这些衍生物的合成产率为58-95％。从该文库中，发现了三种化合物可以有效地使水胶凝，而最高效的水凝剂仅需浓度为0.2 w / v％。

更新日期：2019-11-22

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