Homodiselenacalix[4]arenes: Molecules with Unique Channelled Crystal Structures |
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| Authors: | Dr. Joice Thomas Dr. Liliana Dobrzańska Prof. Luc Van Meervelt Prof. Mario Alfredo Quevedo Prof. Krzysztof Woźniak Marcin Stachowicz Prof. Mario Smet Prof. Wouter Maes Prof. Wim Dehaen |
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| Affiliation: | 1. Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Heverlee, Belgium;2. Biomolecular Architecture, Department of Chemistry, KU Leuven, Heverlee, Belgium;3. Unidad de Investigación y Desarrollo en Tecnología Farmacéutica, CONICET. Departamento de Farmacia, Universidad Nacional de Córdoba, Córdoba, Argentina;4. Department of Chemistry, Warsaw University, Warsaw, Poland;5. Design and Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO-IMOMEC), Hasselt University, Diepenbeek, Belgium |
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| Abstract: | A synthetic route towards homodiselenacalix[4]arene macrocycles is presented, based on the dynamic covalent chemistry of diselenides. The calixarene inner rim is decorated with either alkoxy or tert‐butyl ester groups. Single‐crystal X‐ray analysis of two THF solvates with methoxy and ethoxy substituents reveals the high similarity of their molecular structures and alterations on the supramolecular level. In both crystal structures, solvent channels are present and differ in both shape and capacity. Furthermore, the methoxy‐substituted macrocycle undergoes a single‐crystal‐to‐single‐crystal transformation during which the molecular structure changes its conformation from 1,3‐alternate (loaded with THF/water) to 1,2‐alternate (apohost form). Molecular modelling techniques were applied to explore the conformational and energetic behaviour of the macrocycles. |
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| Keywords: | calixarenes covalent chemistry crystal engineering molecular dynamics selenium |
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