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

Hitoshi Okubo, Fei Feng, Daisuke Nakano, Tomokazu Hirata, Masahiko Yamaguchi, Tokuji Miyashita

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)14855-14864
Number of pages10
JournalTetrahedron
Volume55
Issue number52
DOIs
Publication statusPublished - 1999 Dec 24

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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