%0 journal article
%@ 1860-5397
%A Drescher, S., Haramus, V.M., Garvey, C.J., Meister, A., Blume, A.

%D 2017
%J Beilstein Journal of Organic Chemistry

%P 995-1007 
%R doi:10.3762/bjoc.13.99
%T Aggregation behaviour of a single-chain, phenylene-modified bolalipid and its miscibility with classical phospholipids
%U https://doi.org/10.3762/bjoc.13.99
 
%X In the present work, we describe the synthesis of a single-chain, phenylene-modified bolalipid with two phosphocholine headgroups, PC-C18pPhC18-PC, using a Sonogashira cross-coupling reaction as a key step. The aggregation behaviour was studied as a function of temperature using transmission electron microscopy (TEM), differential scanning calorimetry (DSC), Fourier-transform infrared (FTIR) spectroscopy, and small angle neutron scattering (SANS). We show that our new bolalipid self-assembles into nanofibres, which transform into flexible nanofibres at 27 °C and further to small elongated micelles at 45 °C. Furthermore, the miscibility of the bolalipid with bilayer-forming phosphatidylcholines (DMPC, DPPC, and DSPC) was investigated by means of DSC, TEM, FTIR, and small angle X-ray scattering (SAXS). We could show that the PC-C18pPhC18-PC is partially miscible with saturated phosphatidylcholines; however, closed lipid vesicles with an increased thermal stability were not found. Instead, bilayer fragments and disk-like aggregates are formed.