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 

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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