36645-68-8Relevant articles and documents
Synthesis of symmetrical, single-chain, phenylene/biphenylenemodified bolaamphiphiles
Drescher, Simon,Sonnenberger, Stefan,Meister, Annette,Blume, Alfred,Dobner, Bodo
, p. 1533 - 1543 (2012)
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.
General synthesis and aggregation behaviour of a series of single-chain 1,ω-Bis(phosphocholines)
Drescher, Simon,Meister, Annette,Blume, Alfred,Karlsson, Goeran,Almgren, Mats,Dobner, Bodo
, p. 5300 - 5307 (2008/02/11)
The synthesis and physicochemical characterisation of a series of polymethylene-1,ω-bis(phosphocholines) with even-numbered chain lengths between 22 and 32 carbon atoms is described. Two new synthetic strategies for the preparation of long-chain 1,ω-diols as hydrocarbon building blocks are presented. The temperature-dependent self-assembly of the single-chain bolaamphiphiles was investigated by cryo transmission electron microscopy (cryo-TEM), differential scanning calorimetry (DSC), and Fourier transform infrared spectroscopy (FTIR).
