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Issue 2, 2012
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Conformationally pre-organized and pH-responsive flat dendrons: synthesis and self-assembly at the liquid–solid interface

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Abstract

Efficient Cu-catalyzed 1,3-dipolar cycloaddition reactions have been used to prepare two series of three regioisomers of G-1 and G-2 poly(triazole-pyridine) dendrons. The G-1 and G-2 dendrons consist of branched yet conformationally pre-organized 2,6-bis(phenyl/pyridyl-1,2,3-triazol-4-yl)pyridine (BPTP) monomeric and trimeric cores, respectively, carrying one focal and either two or four peripheral alkyl side chains. In the solid state, the conformation and supramolecular organization were studied by means of a single crystal X-ray structure analysis of one derivative. At the liquid–solid interface, the self-assembly behavior was investigated by scanning tunneling microscopy (STM) on graphite surfaces. Based on the observed supramolecular organization, it appears that the subtle balance between conformational preferences inherent in the dendritic backbone on the one side and the adsorption and packing of the alkyl side chains on the graphite substrate on the other side dictate the overall structure formation in 2D.

Graphical abstract: Conformationally pre-organized and pH-responsive flat dendrons: synthesis and self-assembly at the liquid–solid interface

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Supplementary files

Article information


Submitted
02 Oct 2011
Accepted
03 Nov 2011
First published
02 Dec 2011

Nanoscale, 2012,4, 467-472
Article type
Paper

Conformationally pre-organized and pH-responsive flat dendrons: synthesis and self-assembly at the liquid–solid interface

T. El Malah, A. Ciesielski, L. Piot, S. I. Troyanov, U. Mueller, S. Weidner, P. Samorì and S. Hecht, Nanoscale, 2012, 4, 467
DOI: 10.1039/C1NR11434D

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