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PublicationThe Journal of Physical Chemistry C
Year2014
Volume118 (6)
Pages3069–3077
International

(1R,2S)-Ephedrine: A New Self-Assembling Chiral Template for the Synthesis of Aluminophosphate Frameworks

Authors:Teresa Álvaro Muñoz, Fernando López Arbeloa, J. Perez-Pariente, Luis Gómez-Hortiguela Sáinz
Groups of research:Molecular Sieves
(1R,2S)-(−)-Ephedrine is used as a new structure-directing agent for the synthesis of nanoporous aluminophosphates. This molecule is selected based on the self-aggregating behavior through π–π type interactions between the aromatic rings and the presence of H-bond-forming groups. Additionally, this molecule possesses two chiral centers, which could enhance a potential transfer of chirality to the inorganic framework. Synthesis results showed that (1R,2S)-(−)-ephedrine is very efficient in directing the crystallization of the AFI-type structure in the presence of several catalytically active dopants. A combination of fluorescence spectroscopy and molecular mechanics simulations shows that ephedrine displays a great trend to self-assemble in water solution, establishing not only π–π type interactions between the aromatic rings but also intermolecular H-bonds between NH2 and OH moieties which compete with the formation of H-bonds with water. These molecules are invariably incorporated as aggregates within the AFI structure, regardless of the dopant introduced, showing a very strong trend to self-assemble within nanoporous frameworks as well. The stability of this supramolecular arrangement within the framework is due to a molecular recognition phenomenon based on the establishment of two H-bonds between the H atoms of the amino group and the O atoms of the hydroxyl group of the consecutive dimer, leading to an infinite supramolecular π–π H-bonded chainlike arrangement within the AFI channels.
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