Synthetic Protocols towards Selenacalix[3]triazines

Joice Thomas; Wim Van Rossom; Kristof Van Hecke; Luc Van Meervelt; Mario Smet; WimWouter DehaenMaes

doi:10.1055/s-0032-1318265

Synthesis, Table of Contents

Synthesis 2013; 45(6): 734-742
DOI: 10.1055/s-0032-1318265

paper

Synthetic Protocols towards Selenacalix[3]triazines

Authors

Joice Thomas

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium Fax: +32(16)327990 Email: wim.dehaen@chem.kuleuven.be
Wim Van Rossom

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium Fax: +32(16)327990 Email: wim.dehaen@chem.kuleuven.be
Kristof Van Hecke

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

^cDepartment of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281, Building S3, 9000 Ghent, Belgium
Luc Van Meervelt

^bBiomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
Mario Smet

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium Fax: +32(16)327990 Email: wim.dehaen@chem.kuleuven.be
Wim Dehaen*

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium   Fax: +32(16)327990   Email: wim.dehaen@chem.kuleuven.be

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium   Fax: +32(16)327990   Email: wim.dehaen@chem.kuleuven.be

^dDesign & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO-IMOMEC), Hasselt University, Universitaire Campus, Agoralaan 1 – Building D, 3590 Diepenbeek, Belgium   Email: wouter.maes@uhasselt.be

Abstract

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Abstract

Selenium-bridged heteracalixarenes were synthesized by convenient one-pot S_NAr reactions starting from variously 2-substituted 4,6-dichloro-1,3,5-triazine building blocks. Reactions of these precursors with sodium hydroselenide afforded the selenacalix[3]triazines as the only macrocyclic products. Yields of the cyclotrimers were significantly increased by optimization of the macrocyclization conditions, the optimum parameters being dependent on the triazine functionalization pattern. X-ray diffraction studies allowed unambiguous identification of the structures and comparison with the solid-state features of analogous heteracalixarenes.

Key words

(hetera)calixarenes - macrocycles - selenium - 1,3,5-triazines - substituent effects

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References

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Supplementary Material

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