Formation of a discrete helical assembly and packing pattern through charged hydrogen bonds and van der Waals interactions
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- Formation of a discrete helical assembly and packing pattern through charged hydrogen bonds and van der Waals interactions
- Lee, Ho Yong; Kim, Hae-Jo; Lee, Kyoung Jae; Lah, Myoung Soo; Hong, Jong-In
- MOLECULAR TECTONICS; CHIRAL TRIS(OXAZOLINE); CIRCULAR-DICHROISM; IONIC INTERACTIONS; LIGAND STRANDS; POLAR-SOLVENTS; NETWORKS; CAPSULE; DESIGN; ACID
- Issue Date
- ROYAL SOC CHEMISTRY
- CRYSTENGCOMM, v.9, no.1, pp.78 - 83
- 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 (2(RR)) induces M helicity in [1(2)(.)2(3)] 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.
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