Issue 21, 2009

Macrocyclic oligoureas with xanthene and diphenyl ether units

Abstract

Two cyclic oligoureas with 64- and 80-membered rings in which two sets of three or four rigid xanthene (X) units are connected via flexible diphenyl ether (D) units were synthesized by a stepwise fragment condensation. The compounds were characterized by 1H NMR and ESI mass spectrometry. The structure of the cyclic octamer (XXXDXXXD) was additionally confirmed by single crystal X-ray analysis. The molecule assumes a strongly folded conformation with distorted C2-symmetry, stabilized by intramolecular hydrogen bonds. Surprisingly, intermolecular hydrogen bonds between the macrocycles were not observed. 1H NMR spectra suggest a C2 symmetrical conformation of the octamer in solution also, while its kinetically stable complex with three chloride ions has no symmetry element at all.

Graphical abstract: Macrocyclic oligoureas with xanthene and diphenyl ether units

Supplementary files

Article information

Article type
Paper
Submitted
13 May 2009
Accepted
24 Jul 2009
First published
21 Aug 2009

Org. Biomol. Chem., 2009,7, 4386-4390

Macrocyclic oligoureas with xanthene and diphenyl ether units

D. Meshcheryakov, M. Bolte and V. Böhmer, Org. Biomol. Chem., 2009, 7, 4386 DOI: 10.1039/B909453A

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