Synthetic protocols towards homodithiacalix[n]arenes |
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| Authors: | Joice Thomas Liliana Dobrzańska Mahendra Punjaji Sonawane Mario Smet Wouter Maes |
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| Institution: | 1. Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium;2. Design &3. Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO-IMOMEC), Hasselt University, Universitaire Campus, Agoralaan 1 – Building D, 3590 Diepenbeek, Belgium |
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| Abstract: | Synthetic procedures towards homodithiacalixn]arenes are developed, starting from simple and readily available bifunctional aryl building blocks, by a dynamic covalent chemistry approach. Reaction of 1,3-bis(mercaptomethyl)-5-tert-butyl-2-methoxybenzene under basic conditions leads to a mixture of trimeric, tetrameric and pentameric dimethylenedithia-bridged cyclooligomers, whereas reaction of 5-tert-butyl-2-methoxy-1,3-bis(thiocyanatomethyl) benzene under reducing conditions (and subsequent oxidation) affords the homodithiacalix4]arene macrocycle in a very selective fashion through efficient disulphide exchange chemistry. |
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| Keywords: | (hetera)calixarenes dimethylenedithia bridges dynamic covalent chemistry host–guest chemistry |
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