Chiral molecular assemblies from a novel achiral amphiphilic 2-(heptadecyl) naphtha[2,3]imidazole through interfacial coordination

Jing Yuan; Minghua Liu

doi:10.1021/ja0288486

Chiral molecular assemblies from a novel achiral amphiphilic 2-(heptadecyl) naphtha[2,3]imidazole through interfacial coordination

J Am Chem Soc. 2003 Apr 30;125(17):5051-6. doi: 10.1021/ja0288486.

Authors

Jing Yuan¹, Minghua Liu

Affiliation

¹ CAS Key Laboratory of Colloid and Interface Science, Center for Molecular Science, Institute of Chemistry, The Chinese Academy of Sciences, Beijing 100080, P. R. China.

PMID: 12708854
DOI: 10.1021/ja0288486

Abstract

A novel amphiphilic compound 2-(heptadecyl) naphtha[2,3]imidazole (NpImC17) was synthesized, and its coordination with AgNO(3) in situ in the monolayer at the air/water interface and ex situ in the Langmuir-Blodgett (LB) film on solid substrate has been investigated. It has been found that interfacial coordination between NpImC17 and Ag(I) ion occurred both in the monolayer and in the LB film. It is interesting to note that the Ag(I)-coordinated ultrathin film became chiral although the ligand itself is achiral. It was suggested that the chirality of the Ag(I)-coordinated LB film was developed due to the formation of a helical coordination polymer through the interfacial coordination. To the best of our knowledge, this is the first report on the formation of chiral monolayer and LB films from an achiral molecule through interfacial coordination.