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Issue 37, 2011
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Interfacial assembly of cinnamoyl-terminated bolaamphiphiles through the air/water interface: headgroup-dependent assembly, supramolecular nanotube and photochemical sewing

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Abstract

A series of cinnamoyl-terminated bolaamphiphiles were synthesized and their assemblies at the air/water interface were investigated. It was found that the assembly behaviour depended on the substituted groups on the cinnamoyl unit. The bolaamphiphile with 4-hydroxycinnamoyl head groups (HCDA) was found to assemble into a supramolecular nanotube, while the others formed only layer-structured films. Moreover, the nanotube formed from HCDA showed supramolecular chirality due to the symmetry breaking. Both the layered films and the nanotubes showed photochemical dimerization upon UV irradiation, which were studied from the UV-Vis, FT-IR spectral and MALDI-TOF MS analysis. Interestingly, such dimerization behavior of the cinnamoyl group could be used to stabilize the nanotube of HCDAvia photochemical sewing. During such a process both the supramolecular chirality and the tubular shapes were kept. Remarkably, such a photochemical sewed chiral nanotube could further induce the chirality of an achiral porphyrin derivative assembled on it, and produced the induced chirality without using any chiral molecules.

Graphical abstract: Interfacial assembly of cinnamoyl-terminated bolaamphiphiles through the air/water interface: headgroup-dependent assembly, supramolecular nanotube and photochemical sewing

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Article information


Submitted
14 May 2011
Accepted
04 Aug 2011
First published
22 Aug 2011

Phys. Chem. Chem. Phys., 2011,13, 16520-16529
Article type
Communication

Interfacial assembly of cinnamoyl-terminated bolaamphiphiles through the air/water interface: headgroup-dependent assembly, supramolecular nanotube and photochemical sewing

X. Liu, T. Wang and M. Liu, Phys. Chem. Chem. Phys., 2011, 13, 16520
DOI: 10.1039/C1CP21561B

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