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Self-assembly of chiral (1R,2S)-ephedrine and (1S,2S)-pseudoephedrine into low-dimensional aluminophosphate materials driven by their amphiphilic nature†
Physical Chemistry Chemical Physics ( IF 3.3 ) Pub Date : 2018-02-26 00:00:00 , DOI: 10.1039/c7cp08573g
Beatriz Bernardo-Maestro 1, 2, 3, 4 , Elisa Garrido-Martín 1, 2, 3, 4 , Fernando López-Arbeloa 4, 5, 6, 7 , Joaquín Pérez-Pariente 1, 2, 3, 4 , Luis Gómez-Hortigüela 1, 2, 3, 4
Affiliation  

In an attempt to promote the crystallization of chiral inorganic frameworks, we explore the ability of chiral (1R,2S)-ephedrine and its diastereoisomer (1S,2S)-pseudoephedrine to act as organic building blocks for the crystallization of hybrid organo-inorganic aluminophosphate frameworks in the presence of fluoride. These molecules were selected because of their particular molecular asymmetric structure, which enables a rich supramolecular chemistry and a potential chiral recognition phenomenon during crystallization. Up to four new low-dimensional materials have been produced, wherein the organic molecules form an organic bilayer in-between the inorganic networks. We analyze by molecular simulations the trend of these chiral molecules to form these types of framework, which is directly related to their amphiphilic nature that triggers a strong self-assembly through hydrophobic interactions between aromatic rings and hydrophilic interactions with the fluoro-aluminophosphate inorganic units. Such a self-assembly process is strongly dependent on the concentration of the organic molecules.

中文翻译:

手性(1 R,2 S)-麻黄碱和(1 S,2 S)-伪麻黄碱的自组装成两亲性质驱动的低维磷酸铝材料

为了促进手性无机骨架的结晶,我们探索了手性(1 R,2 S)-麻黄碱及其非对映异构体(1 S,2 S)-伪麻黄碱在氟化物存在下充当有机-无机铝磷酸盐杂化骨架结晶的有机结构单元。选择这些分子的原因是它们具有特殊的分子不对称结构,从而可以实现丰富的超分子化学和结晶过程中潜在的手性识别现象。已经生产了多达四种新的低维材料,其中有机分子在无机网络之间形成有机双层。我们通过分子模拟分析了这些手性分子形成这些类型骨架的趋势,这与它们的两亲性直接相关,两亲性通过芳香环之间的疏水相互作用以及与氟铝磷酸盐无机单元的亲水相互作用触发了强烈的自组装。
更新日期:2018-02-26
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