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Synthesis 2010(6): 953-958  
DOI: 10.1055/s-0029-1218684
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Tuning the Polarity of Hierarchically Assembled Helicates

Miriam Baumerta, Markus Albrecht*a, Henrik D. F. Winklerb, Christoph A. Schalleyb
a Institut für Organische Chemie der RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092385; e-Mail: Markus.Albrecht@oc.rwth-aachen.de;
b Institut für Chemie und Biochemie - Organische Chemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany
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Publication History

Received 27 August 2009
Publication Date:
24 February 2010 (online)

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Abstract

Catechol ligands bearing ester groups in 3-position (1a,b, 2) are building blocks for the formation of triply lithium-bridged dinuclear helicate-type complexes [Li3(1a,b,2)6Ti2]-. Attachment of appropriate functionalities at the ester unit allows the fine tuning of the polarity of the compounds to afford solubility in highly nonpolar as well as highly polar solvents. The investigations show that the internal dinuclear core is stable in a broad variety of solvents, even in water.

Key words

helicates - dinuclear complexes - esters - hierarchical self-assembly - templates

    References

  • 1a Lehn JM. Supramolecular Chemistry, Concepts and Perspectives   VCH; Weinheim: 1996. 
    Google Scholar
  • 1b Steed JW. Atwood JL. Supramolecular Chemistry   Wiley-VCH; Weinheim: 2002. 
    Google Scholar
  • 2a Abedin MJ. Liepold L. Suci P. Young M. Douglas T. J. Am. Chem. Soc.  2009,  131:  4346 
    Google Scholar
  • 2b Yu T.-B. Bai JZ. Guan Z. Angew. Chem. Int. Ed.  2009,  48:  1097 ; Angew. Chem. 2009, 121, 1117
    Google Scholar
  • 2c Pradeep CP. Long D.-L. Newton GN. Song Y.-F. Cronin L. Angew. Chem. Int. Ed.  2008,  47:  4388 ; Angew. Chem. 2008, 120, 4460
    Google Scholar
  • 2d Cheglakov Z. Weizmann Y. Braunschweig AB. Wilner OI. Willner I. Angew. Chem. Int. Ed.  2008,  47:  126 ; Angew. Chem. 2008, 120, 132
    Google Scholar
  • 2e Matsuura K. Murasato K. Kimizuka N. J. Am. Chem. Soc.  2005,  127:  10148 
    Google Scholar
  • 3a Klug A. Angew. Chem., Int. Ed. Engl.  1983,  22:  565 ; Angew. Chem. 1983, 95, 579
    Google Scholar
  • 3b Tan WS. Lewis CL. Horelik NE. Pregibon DC. Doyle PS. Yi H. Langmuir  2008,  24:  12483 
    Google Scholar
  • 4a Albrecht M. Baumert M. Klankermayer J. Kogej M. Schalley CA. Fröhlich R. Dalton Trans.  2006,  4395 
    Google Scholar
  • 4b Albrecht M. Fiege M. Baumert M. de Groot M. Fröhlich R. Russo L. Rissanen K. Eur. J. Inorg. Chem.  2007,  609 
    Google Scholar
  • 5 Albrecht M. Mirtschin S. de Groot M. Janser I. Runsink J. Raabe G. Kogej M. Schalley CA. Fröhlich R. J. Am. Chem. Soc.  2005,  127:  10371 
    CrossrefGoogle Scholar
  • Reviews on helicates:
  • 6a Piguet C. Bernardinelli G. Hopfgartner G. Chem. Rev.  1997,  97:  2005 
    Google Scholar
  • 6b Albrecht M. Chem. Rev.  2001,  101:  3457 
    Google Scholar
  • 6c Hannon MJ. Childs LJ. Supramol. Chem.  2004,  16:  7 
    Google Scholar
  • 6d Albrecht M. Bull. Chem. Soc. Jpn.  2007,  80:  797 
    Google Scholar
  • 7 Terazzi E. Torelli S. Bernardenielli G. Rivera J.-P. Benech J.-M. Bourgogne C. Donnio B. Guillon D. Imbert DG. Bünzli J.-C. Pinto A. Jeannerat D. Piguet C. J. Am. Chem. Soc.  2005,  127:  888 
    CrossrefGoogle Scholar
  • 8 Tanabe K. Yasuda K. Yoshio M. Kato T. Org. Lett.  2007,  9:  4271 
    CrossrefGoogle Scholar
  • 9a Williamson W. Liebigs Ann. Chem.  1851,  77:  37 
    Google Scholar
  • 9b Feuer H. Hooz J. In The Chemistry of the Ether Linkage   Patai S. Wiley; New York: 1967.  p.445-498  
    Google Scholar
  • 9c Okuro K. Kinbara K. Tsumoto K. Ishii N. Aida T. J. Am. Chem. Soc.  2009,  131:  1626 
    Google Scholar