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Facile,high-yielding synthesis of deepened cavitands: a synthetic and theoretical study |
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| Authors: | Zsolt Csók Tamás Kégl László Párkányi Ágnes Varga Sándor Kunsági-Máté László Kollár |
| Affiliation: | 1. Department of Inorganic Chemistry , University of Pécs , Ifjúság 6, H-7624, Pécs, Hungary zscsok@gmail.com;3. Department of Inorganic Chemistry , University of Pécs , Ifjúság 6, H-7624, Pécs, Hungary;4. X-ray Diffraction Laboratory, Institute of Structural Chemistry, Chemical Research Center, Hungrian Academy of Science , Pusztaszeri 59-67, H-1025, Budapest, Hungary;5. Department of General and Physical Chemistry , University of Pécs , Ifjúság 6, H-7624, Pécs, Hungary |
| Abstract: | A wide variety of 2-methyl-resorcinol-based deepened cavitands were synthesised from readily available reagents in a four-step procedure with overall yields of up to 62%. A systematic variation of the rim was carried out by building up a flexible upper aromatic wall on the rigid cavitand platform through CH2, CH2O and CH2OCH2 spacers. These aromatic walls were further extended by a Suzuki cross-coupling reaction. Full characterisation of the synthesised cavitands was carried out. The solid-state structure of tetrakis(phenoxymethyl)cavitand was determined by X-ray crystallography. Gas-phase theoretical calculations for this molecule predict the presence of weak T-shaped interactions between the upper phenyl rings. The host–guest complex formation ability of two deepened cavitand hosts towards 4-chloro-benzotrifluoride was proved by photoluminescence method. |
| Keywords: | supramolecular chemistry host–guest systems cavitands π interactions |