Monatshefte für Chemie - Chemical Monthly

, Volume 143, Issue 11, pp 1533–1543 | Cite as

Synthesis of symmetrical, single-chain, phenylene/biphenylene-modified bolaamphiphiles

  • Simon Drescher
  • Stefan Sonnenberger
  • Annette Meister
  • Alfred Blume
  • Bodo Dobner
Original Paper


Two new, symmetrical, phenylene- or biphenylene-modified bolaamphiphiles bearing two phosphocholine headgroups and an alkyl spacer chain length of 32 and 36 carbon atoms, respectively, have been synthesised. The key step was the Cu(II)-catalysed Grignard reaction used either as a simultaneous bis-coupling procedure or in a stepwise homo-coupling. Particularly with the use of the homo-coupling, we were able to separate the phenylene-free by-products from the desired products. This homo-coupling additionally offered the possibility of preparing unsymmetrical bolaamphiphiles. Conversion of the diols into bipolar phospholipids was achieved by bis-phosphorylation with β-bromoethylphosphoric acid dichloride and subsequent quarternisation with trimethylamine. Unlike previous studies with aliphatic bolaamphiphiles that formed flexible nanofibres in aqueous suspension, the bolaamphiphiles of the present study, containing phenylene- and biphenylene groups in the middle part of the alkyl spacer chain, formed small ellipsoidal aggregates at ambient temperature.

Graphical abstract


Grignard reactions Lipids Bolaamphiphiles Nanostructures Phosphates 



This work was supported by grants from the Deutsche Forschungsgemeinschaft (projects Bl 182/19-3 and Do 463/4-2). We thank Prof. Andrea Sinz and Dr. Christian Ihling (Department of Pharmaceutical Chemistry and Bioanalytics, Martin-Luther-University Halle-Wittenberg) for the high resolution mass spectrometry analysis. The support of Dr. Gerd Hause (Biocenter, Martin-Luther-University Halle-Wittenberg) by providing us access to the electron microscope facility is greatly appreciated. Finally, S.D. and B.D. thank Dipl.-Pharm. Susann Althaus and Dr. Beate Stiebitz for the help in the synthesis.

Supplementary material

706_2012_833_MOESM1_ESM.doc (847 kb)
Supplementary material 1 (DOC 849 kb)


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Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  • Simon Drescher
    • 1
  • Stefan Sonnenberger
    • 1
  • Annette Meister
    • 2
  • Alfred Blume
    • 2
  • Bodo Dobner
    • 1
  1. 1.Institute of PharmacyMartin-Luther-University Halle-WittenbergHalle (Saale)Germany
  2. 2.Institute of ChemistryMartin-Luther-University Halle-WittenbergHalle (Saale)Germany

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