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    Chiral supramolecular assemblies from some achiral Schiff bases without alkyl chain through the organization at the air/water interface

    Year: 2006

    Journal: Colloids and Surfaces A: Physicochemical and Engineering Aspects, Volumes 284-285, 15 August 2006, Pages 70-73, 20111221

    Authors: Peizhi Guo, and Minghua Liu

    Organizations: CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, Institute of Chemistry, The Chinese Academy of Sciences, Beijing 100080, PR China, Graduate School of the Chinese Academy of Sciences, The Chinese Academy of Sciences, Beijing 100080, PR China

    Two novel Schiff bases, 1-benzthiazolyliminomethyl-2-naphthol (TSN) and 1-(6′-chlorobenzthiazolyliminomethyl)-2-naphthol (ClTSN), were synthesized and their molecualr assemblies at the air/water interface were investigated. Both of the compounds could be spread on water surface although they have no alkyl chains. The Schiff base molecules formed J- or H-aggregate in the Langmuir–Schaefer (LS) films transferred from water surface. In AFM, a multilayer film formation was observed. It is interesting to note that the LS films of achiral TSN and ClTSN transferred from water surface showed chirality. The supramolecular chirality in these LS films was suggested to be due to a cooperative stereoregular π–π stacking of the functional groups in a helical sense.