Equilibrium structure and dynamics of (2R, 3R)-(+)-bis(decyloxy)succinic acid at the air-water interface

A twin-tailed, twin-chiral fatty acid, (2R,3R)-(+)-bis(decyloxy)succinic acid was synthesized and its two dimensional behavior at the air-water interface was examined. The pH of the subphase had a profound effect on the monolayer formation. On acidic subphase, stable monolayers with increased area per molecule due to hydrogen bonding and bilayers at collapse pressures were observed. Highly compressible films were formed at 40°C, while stable monolayers with increased area were observed at sub-room temperatures. Langmuir monolayers formed on subphases containing 1 mM ZnCl2 and CaCl 2 revealed two dimensional metal complex formation with Zn 2+ forming a chelate-type complex, while Ca2+ formed an ionic-type complex. Monolayers transferred from the condensed phase onto hydrophilic Si(100) and quartz substrates revealed the formation of bilayers through transfer-induced monolayer buckling. Compression induced crystallites in 2D from monolayers and vesicle-like supramolecular structures from multilayers were the noted LB film characteristics, adopting optical imaging and electron microscopy. The interfacial monolayer structure studied through molecular dynamics simulation revealed the order and packing at a molecular level; monolayers adsorbed at various simulated specific areas of the molecule corroborated the (π-A) isotherm and the formation of a hexagonal lattice at the air-water interface. © 2008 American Chemical Society.