In this work, we describe a general and efficient fragment condensation method for the synthesis of monoselenacalix[4]arene as a new member of the broad calixarene family. The key fragments were obtained from the starting p-tert-butylphenol by reaction with in situ generated SeCl2 or from its formyl derivative by reaction with SeO2 in pyridine. The availability of both fragments allowed us to test two different independent macrocyclization routes, leading to the final selenacalixarene in good yields. The first successful attempts to immobilize the new system were made, and the basic dynamics of the macrocycles in solution were studied using VT NMR techniques. The selenium analogue of calix[4]arene was successfully immobilized in the cone conformation, suggesting its potential use in supramolecular chemistry.

Department of Analytical Chemistry University of Chemistry and Technology Prague Technická 5 166 28 Prague 6 Czech Republic

Department of Organic Chemistry University of Chemistry and Technology Prague Technická 5 166 28 Prague 6 Czech Republic

Institute of Physics AS CR v v i Na Slovance 1999 2 182 21 Prague 8 Czech Republic

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