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Macrocyclic Ethers and Their Inclusion Complexes
Author(s) -
Ratilainen Jari,
Airola Karri,
Nieger Martin,
Böhme Marc,
Huuskonen Juhani,
Rissanen Kari,
Nieger D. R. M.
Publication year - 1997
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19970030515
Subject(s) - dichloromethane , chemistry , ether , supramolecular chemistry , benzene , diethyl ether , diphenylmethane , inclusion compound , molecule , organic chemistry , polymer chemistry , solvent , catalysis
The synthesis and characterisation of eleven new macrocyclic ethers (up to 96‐membered [6+6] gigantocycle) with well‐defined cavities are described. Syntheses of the macrocycles M1–M7 were performed under high‐dilution conditions. A “supramolecular” purification method was used for the small [2+2] macrocycles M3–M7 , which separated selectively from the reaction mixture on recrystallisation from a dichloromethane/diethyl ether solution mixture. This proved to be an excellent method for purifying [2+2] macrocyclic ethers containing 1,1‐diphenylmethane moieties, and the separation was nearly quantitative. Molecular inclusion of dichloromethane in the cavities of noncovalently bonded macrocyclic ethers M2–M5 was studied by X‐ray diffraction in the solid state. Additionally, clathrate formation was found for macrocycles M1 (including diethyl ether), M2 (including water), M6 (including benzene) and M7 (including benzene).