Synthesis of phospholipids containing perfluorooctyl group and their interfacial properties

Effect of the fluorination degree of hydrophobic chains on the monolayer behavior of unsaturated diacylphosphatidylcholines bearing partially fluorinated 9-octadecynoyl (stearoloyl) groups at the air–water interface

“…The value of c as an indicator of monolayer stability increased with the fluorination degree of hydrophobic chains, i.e., n, and the monolayer stability of F 8 StA was the highest among F n StAs. This result is consistent with our previous conclusion obtained from es measurements [18]. It should be noted that the isotherm for StA shifted to a smaller area by approximately 0.08 nm 2 /molecule compared with the previous data [23,34,35], whereas the c value for StA (ca.…”

“…F n StAs (n = 1, 2, 4, 8) and StA were prepared with purities of >97% as previously described [15,18]. DF n StPCs (n = 1, 2, 4, 8, Fig.…”

“…Table 1 summarizes the monolayer parameters for F n StAs and StA, i.e., the limiting area, A 0 , the liftoff area, A liftoff (defined as the point on the C −1 s − A isotherm where the curves abruptly rise from the baseline of C −1 s = 1 mN/m), and the collapse pressure, c , at the collapse area, A c . Table 1 also presents our previous data regarding es for F n StAs and StA [18].…”

“…Therefore, the introduction of fluorinated chains into C 18 fatty acid molecules was considered effective in improving monolayer stability against lateral compression [15]. We also observed that progressive fluorinations of the terminal segment of unsaturated fatty acids, such as 9-octadecynoic acid (stearolic acid, StA) [18] and 9-octadecenoic acid (oleic acid, OA) [19], gradually increase monolayer stability. These findings provided information on the extent to which the fluorination degree of hydrophobic chains is required to improve membrane stability.…”

Dynamic Molecular Behavior of Semi-Fluorinated Oleic, Elaidic and Stearic Acids in the Liquid State

“…They concluded that the intermolecular interaction among fatty acid molecules in the bulk phase become progressively weaker with increasing fluorine content in the stearolic acid molecule. Furthermore, Takagi et al 29 . reported that SF-phospholipids containing a perfluorooctyl group in their molecules have a higher ESP value than the corresponding ordinary phos- band is assigned to the CO vibration of free carboxylic group; large and relatively sharp 1711-cm -1 band, assigned to CO vibration of dimeric carboxylic group; the 1665-cm -1 band, which is observed only for SF-oleic acid, assigned to the vibration of the double bond of SF-oleic acid.…”