Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland
One of the crucial problems in supramolecular chemistry is designing a ligand able to bind the specific guest molecule. Another difficulty is an effective synthesis of macrocyclic compounds of desired size and structure. A new synthetic methodology, dynamic combinatorial chemistry (DCC), can solve both of these problems.1 The idea is based on the construction of a dynamic combinatorial library using a reversible reaction of a,w-bifunctional substrates, e.g. dialdehydes and diamines.2 Addition of a substance (template, T) that can noncovalently interact with members of the library, changes the equilibrium of the system. Thus, the composition of the library represents the strength of interaction of the members of the library and the template.
Herein we present the study of the reaction between terminal aromatic dialdehydes and aliphatic a,w-diamines, in the presence of several inorganic (alkaline metals) and organic (quaternary ammonium salts) templates. This approach allows synthesizing and testing a great number of compounds in a short time, thus requires adequately fast analytical technique. The composition of the libraries was studied using electro spray ionization mass spectrometry (ESI-MS). Finally, the synthesis of selected macrocyclic receptors containing furan units,3 using DCC methodology, will be shown.
1. Rowan, S.J.; Cantrill, S.J.; Cousins, G.R.L.; Sanders, J.K.M.; Stoddart, J.F., Angew. Chem. Int. Ed. 2002, 41, 899~952.
2. Jazwinski, J.; Lehn, J-M.; Meric, R.; Vigneron, J-P.; Cesario, M., Tetrahedron Lett. 1987, 28, 3489~3492.
3. Pajewski, R.; Ostaszewski, R.; Jurczak, J., Supramolecular Chem. 2000, 12, 97~100.