Spreading Behavior of Optically Active Macrocycloamides Consisting of Helical Chiral Units at the Air−Water Interface and the Formation of Langmuir−Blodgett Films

Abstract

The spreading behavior of a new type of chiral compound, namely a series of optically active macrocycloamides (( P )-(−)- 1, ( P, P )-(+)- 2, ( P,P, P )-(+)- 3, and ( P,P,P, P )-(+)- 4 ) consisting of the helical chiral unit 1,12-dimethylbenzo[ c ]phenanthrene-5,8-dicarboxylate, and dianiline derivatives, on the water surface was investigated by measuring surface pressure (π)−area ( A ) isotherms, with the aim of producing a new type of chiral Langmuir−Blodgett film. Among the four compounds investigated, ( P )-(−)- 1 and ( P, P )-(+)- 2 formed condensed monolayers. Moreover, the monolayer of ( P )-(−)- 1 could be successively transferred onto solid supports by both downward and upward strokes, yielding Y-type LB films. An optically active LB film based on helical chirality was produced for the first time. The properties of the chiral LB film are discussed.