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Neue wasserlösliche makrobicyclische Großhohlräume
Author(s) -
Wallon Alexander,
PeterKatalinića Jasna,
Werner Ute,
Müller Walter M.,
Vögtle Fritz
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901230224
Subject(s) - chemistry , mass spectrometry , nuclear magnetic resonance spectroscopy , spectroscopy , fluorescence spectroscopy , stereochemistry , fluorescence , crystallography , chromatography , physics , quantum mechanics
New Watersoluble Macrobicyclic Cavities The watersoluble macrobicyclic compounds 1, 3, 5a , and 5b have been synthesized for the first time bearing large endolipophilic cavities of different sizes and shapes. They were studied with respect to their interactions towards lipophilic guest compounds. The “in/out” isomerism of the hitherto largest endolipophilic cavities 4a, 4b, 5a , and 5b has been investigated by 1 H‐, 13 C‐NMR spectroscopy and FAB mass spectrometry. The absence of significant 1 H‐NMR high‐field shifts in hostguest studies is attributed to the rigidity of cavities 1 and 3 , whilst the isomeric cavities 5a and 5b contain very large openings. Orientational fluorescence spectroscopy investigations, however, suggest hostguest interactions of the isomers 5a and 5b with ammonium 8‐anilino‐1‐naphthalenesulfonate (8,1‐ANS).