Non‐Rusty [2]Catenanes with Huge Rings and Their Polymers

作者: Adelheid Godt

DOI: 10.1002/EJOC.200300503

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摘要: We describe the design and synthetic realisation of [2]catenanes characterised by having huge rings that can rotate freely shift laterally within constraints concatenation. The strategy, which is based on using a carbonate group as covalent template oxidative dimerization alkynes to achieve ring formation, versatile with respect size presence functional groups. monocyclic constitutional isomer catenane available simple exchange steps in sequence. EPR spectroscopy revealed solution catenanes adopt all possible co-conformations equal abundances. thermotropic liquid crystallinity their corresponding non-intertwined macrocycles proves intermolecular ordering bulk phase. were polymerized through ester formation acyclic diene metathesis. All poly[2] have rather low degrees polymerisation ( approximate 10), possibly because cyclisation occurs. For preparation [n]catenanes n > 3, we propose fusing so crucial threading need only occur during synthesis smallest catenane.

参考文章(113)
D. Tindall, J. H. Pawlow, K. B. Wagener, Recent Advances in ADMET Chemistry Topics in Organometallic Chemistry. pp. 183- 198 ,(1998) , 10.1007/3-540-69708-X_7
Adam Sobanski, Roland Schmieder, Fritz Vögtle, Topologische Stereochemie und Chiralität Chemie in Unserer Zeit. ,vol. 34, pp. 160- 169 ,(2000) , 10.1002/1521-3781(200006)34:3<160::AID-CIUZ160>3.0.CO;2-6
Matthew C. T. Fyfe, Peter T. Glink, Stephan Menzer, J. Fraser Stoddart, Andrew J. P. White, David J. Williams, Anion‐Assisted Self‐Assembly Angewandte Chemie. ,vol. 36, pp. 2068- 2070 ,(1997) , 10.1002/ANIE.199720681
Nicolas Belfrekh, Christiane Dietrich-Buchecker, Jean-Pierre Sauvage, Unexpected synthesis of an 8-shaped macrocycle instead of an interlocking-ring system. Inorganic Chemistry. ,vol. 39, pp. 5169- 5172 ,(2000) , 10.1021/IC991502K
M. Hutnik, A. S. Argon, U. W. Suter, Conformational characteristics of the polycarbonate of 4,4'-isopropylidenediphenol Macromolecules. ,vol. 24, pp. 5956- 5961 ,(1991) , 10.1021/MA00022A010
Miguel E. Padilla-Tosta, O. Danny Fox, Michael G. B. Drew, Paul D. Beer, Self-Assembly of a Mixed-Valence Copper(II)/Copper(III) Dithiocarbamate Catenane Angewandte Chemie International Edition. ,vol. 40, pp. 4235- 4239 ,(2001) , 10.1002/1521-3773(20011119)40:22<4235::AID-ANIE4235>3.0.CO;2-1
David O'Krongly, Samuel R. Denmeade, Michael Y. Chiang, Ronald Breslow, Efficient Triple Coupling Reaction To Produce a Self-Adjusting Molecular Cage Journal of the American Chemical Society. ,vol. 107, pp. 5544- 5545 ,(1985) , 10.1021/JA00305A047
Akiko Hori, Akihiko Akasaka, Kumar Biradha, Shigeru Sakamoto, Kentaro Yamaguchi, Makoto Fujita, Chirality Induction through the Reversible Catenation of Coordination Rings Angewandte Chemie. ,vol. 41, pp. 3269- 3272 ,(2002) , 10.1002/1521-3773(20020902)41:17<3269::AID-ANIE3269>3.0.CO;2-9
Guy J Clarkson, David A Leigh, Richard A Smith, From catenanes to mechanically-linked polymers Current Opinion in Solid State & Materials Science. ,vol. 3, pp. 579- 584 ,(1998) , 10.1016/S1359-0286(98)80029-6
Francis Bitsch, Christiane O. Dietrich-Buchecker, Abdel Kader Khemiss, Jean Pierre Sauvage, Alain Van Dorsselaer, Multiring interlocked systems: structure elucidation by electrospray mass spectrometry Journal of the American Chemical Society. ,vol. 113, pp. 4023- 4025 ,(1991) , 10.1021/JA00010A072