In Silico Design of Cylindrophanes: The Role of Functional Groups in a Fluoride Selective Host |
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Authors: | M.Sc. Ina Østrøm Dr. Alexandre O. Ortolan Dr. Giovanni F. Caramori Prof. Dr. Mark Mascal Prof. Dr. Alvaro Muñoz-Castro Dr. Renato L. T. Parreira |
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Affiliation: | 1. Departamento de Química, Universidade Federal de Santa Catarina, Campus Universitário Trindade, CP 476, Florianópolis, SC, 88040-900 Brazil;2. Department of Chemistry, University of California Davis, 1 Shields Avenue, Davis, CA 95616 USA;3. Laboratorio de Química Inorgánica y Materiales Moleculares, Facultad de Ingeniería, Universidad Autonoma de Chile, Llano Subercaseaux 2801, San Miguel, Santiago, Chile;4. Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, 14404-600 Franca, SP, Brazil |
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Abstract: | Molecular recognition is the key driver in the formation of supramolecular complexes, enabling the selective encapsulation of specific guests. Here, we explore the delicate balance between different energetic terms in the formation of an efficient host for fluoride anions based on a cylindrophane structure, which can be achieved by the incorporation of ligand sites into a cyanuric acid based cyclophane framework, resulting a close proximity between the ammonium hydrogens and the anion. This study describes the character and contribution of different energetic and repulsive terms that favor the efficient inclusion of fluoride. Our findings are useful for further rational design and synthesis of efficient and highly selective fluoride hosts, which have been generally less well described than complexing agents for other halides. |
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Keywords: | Anion-π cylindrophanes fluoride hosts hydrogen bond non-covalent interactions |
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