Self-assembly of chiral (1R,2S)-ephedrine and (1S,2S)-pseudoephedrine into low-dimensional aluminophosphate materials driven by their amphiphilic natureElectronic supplementary information (ESI) available: In situ XRD, NMR spectra, and molecular pictures are included. See DOI: 10.1039/c7cp08573g

• Main Authors: Bernardo-Maestro, Beatriz, Garrido-Martín, Elisa, López-Arbeloa, Fernando, Pérez-Pariente, Joaquín, Gómez-Hortigüela, Luis
• Format: Journal Article
• Language: English
• Published: 28.03.2018
• ISSN: 1463-9076; 1463-9084
• DOI: 10.1039/c7cp08573g

In an attempt to promote the crystallization of chiral inorganic frameworks, we explore the ability of chiral (1 R ,2 S )-ephedrine and its diastereoisomer (1 S ,2 S )-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. Supramolecular aggregation of amphiphilic ephedrine and pseudoephedrine provokes the formation of large organic bilayers and the crystallization of low-dimensional materials.