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Issue 1, 2007
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Formation of a discrete helical assembly and packing pattern through charged hydrogen bonds and van der Waals interactions

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Abstract

We report the selective formation of a self-assembled discrete helical assembly with handedness through charged hydrogen bonds in aqueous solution and solid state. A helical assembly is obtained by simply mixing tris(imidazoline) (1) and (rac)-trans-cyclohexane-1,2-dicarboxylic acid (2) in a 2 : 3 ratio in water and methanol. The formation of an ion aggregate is fully supported by NMR, MALDI-TOF mass spectroscopy, and X-ray analysis. Helicity of the 2 : 3 complex is determined by the chirality of 2. For example, (1R,2R)-trans-cyclohexane-1,2-dicarboxylic acid (2RR) induces Mhelicity in [12·23] and vice versa. Each complex is enantiomerically pure as equal amounts of the P and M helical complexes are formed with racemic 2. P- and M-helical assemblies are stacked by turns because PMPM stacking is denser than PP or MM stacking.

Graphical abstract: Formation of a discrete helical assembly and packing pattern through charged hydrogen bonds and van der Waals interactions

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Publication details

The article was received on 21 Jul 2006, accepted on 24 Oct 2006 and first published on 06 Nov 2006


Article type: Paper
DOI: 10.1039/B610512B
Citation: CrystEngComm, 2007,9, 78-83
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    Formation of a discrete helical assembly and packing pattern through charged hydrogen bonds and van der Waals interactions

    H. Y. Lee, H. Kim, K. J. Lee, M. S. Lah and J. Hong, CrystEngComm, 2007, 9, 78
    DOI: 10.1039/B610512B

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