22513-81-1Relevant articles and documents
Synthesis of symmetrical, single-chain, phenylene/biphenylenemodified bolaamphiphiles
Drescher, Simon,Sonnenberger, Stefan,Meister, Annette,Blume, Alfred,Dobner, Bodo
, p. 1533 - 1543 (2013/02/22)
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 homocoupling. 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. Springer-Verlag 2012.
