Journal
TETRAHEDRON
Volume 68, Issue 46, Pages 9419-9422Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.09.006
Keywords
Macrocyclic ligands; Template synthesis; Host-guest systems; Receptors; Pi interactions
Categories
Funding
- Polish Ministry of Science and Higher Education [N N204 187839]
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A new, very efficient, and selective preparation method of peralkylated pillar[5]arenes is presented. By replacing typical Lewis acids with trifluoroacetic acid (TFA) we were able to eliminate the need of anhydrous conditions without a loss of effectiveness. The method is highly practical: a) it is moisture-insensitive, b) starting from simple and cheap reagents and reactants, and c) allows for chromatography-free isolation of the products. The results indicate that the interactions with solvent molecules can modulate stability of the products and influence the reaction outcome. Dichloromethane (DCM) and dichloroethane (DCE) are complexed within the cyclopentamer cavity with association constants of 120 M-1 and 600 M-1, respectively (CDCl3). The interactions involve a combination of hydrogen-pi and halogen-pi bonds. (C) 2012 Elsevier Ltd. All rights reserved.
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