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Supramolecular Chirality from an Achiral Azobenzene Derivative through the Interfacial Assembly: Effect of the Configuration of Azobenzene Unit

Year: 2006

Journal: Langmuir, 2006, 22 (24), pp 10246–10250, 20111221

Authors: Yiqun Zhang, Penglei Chen, and Minghua Liu

Organizations: Beijing National Laboratory for Molecular Science, CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, 100080 Beijing, China

The Langmuir−Schaefer (LS) films of an achiral azobenzene derivative, 4-octyl-4‘-(5-carboxypentamethyleneoxy) azobenzene (C8AzoC5), were fabricated and their optical activities were investigated. It was found that the LS film of the trans-C8AzoC5 showed strong Cotton effect, while that of cis-C8AzoC5 did not. The characterization of the LS films by UV−vis, Fourier transform infrared (FT-IR) spectra, and X-ray diffraction (XRD) revealed that this interesting phenomenon was due to the different packing of the azobenzene unit in the LS film. The planar conjugated trans-azobenzene favored ordered cooperative packing in a helical sense and produced the supramolecular chirality, while the cis-isomer did not due to the bulky twisted configuration.