Synthesis and monolayer behaviors of optically active 1,12- dimethylbenzo[c]phenanthrene-5,8-diamides and the formation of chiral Langmuir-Blodgett films

Article abstract of DOI:10.1016/S0040-4020(99)00969-2

We previously reported that an optically active cyclic amide consisting of a helical chiral 1,12-dimethylbenzo[c]phenanthrene- 5,8-dicarboxylic acid forms a stable monolayer on the water surface, and that the monolayer can be transferred on a solid support giving optically active Langmuir-Blodgett (LB) films. In this study, several related amides were synthesized, and their monolayer behaviors were investigated with expectation to prepare optically active LB films possessing functional groups. The result indicates that the cyclic amide structure and cyclohexyl moiety are essential for the formation of stable monolayer on the water surface. N-Alkylation of the secondary amide does not seriously affect the formation of monolayer, and chiral LB films are obtained by N,N'-bis(3-mercaptopropyl) derivative of the cyclic amide.