Homoselenacalix[4]arenes: synthetic exploration and metallosupramolecular chemistry

Joice Thomas; Liliana Dobrzańska; Kristof Van Hecke; Mahendra P. Sonawane; Koen Robeyns; Luc Van Meervelt; Krzysztof Woźniak; Mario Smet; Wouter Maes; Wim Dehaen

doi:10.1039/C2OB25760B

Homoselenacalix[4]arenes: synthetic exploration and metallosupramolecular chemistry†

Joice Thomas,^a Liliana Dobrzańska,^a Kristof Van Hecke,^bc Mahendra P. Sonawane,^a Koen Robeyns,^bd Luc Van Meervelt,^b Krzysztof Woźniak,^e Mario Smet,^a Wouter Maes*^af and Wim Dehaen*^a

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* Corresponding authors

^a Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
E-mail: wim.dehaen@chem.kuleuven.be
Fax: +32 16327990
Tel: +32 16327439

^b Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

^c Department of Inorganic and Physical Chemistry Group, Ghent University, Krijgslaan 281, Building S3, 9000 Ghent, Belgium

^d Institute of Condensed Matter and Nanosciences (IMCN), Université Catholique de Louvain (UCL), Bâtiment Lavoisier, Place Louis Pasteur 1 (Bte 3), 1348 Louvain-la-Neuve, Belgium

^e Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland

^f Design & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO-IMOMEC), Hasselt University, Universitaire Campus, Agoralaan 1 – Building D, 3590 Diepenbeek, Belgium
E-mail: wouter.maes@uhasselt.be
Fax: +32 11268299
Tel: +32 11268312

Abstract

Homoselenacalix[4]arenes were synthesized by a [2 + 2] reductive coupling protocol favouring the cyclotetramers. The inner and outer-rim decoration was varied and a bicyclic derivative was prepared by a similar one-pot procedure. Conformational analysis in solution and the solid state showed noticeable differences between the homoselenacalix[4]arenes and the analogous homothiacalix[4]arenes and provided insight into the metal binding potential of the Se-bridged macrocycles. The homoselenacalix[4]arenes were found to bind Ag(I). Complexation was visualized in the solid state and different packing networks were formed depending on the counter ions applied.

Organic & Biomolecular Chemistry

Homoselenacalix[4]arenes: synthetic exploration and metallosupramolecular chemistry†

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Homoselenacalix[4]arenes: synthetic exploration and metallosupramolecular chemistry

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