Journal
CRYSTAL GROWTH & DESIGN
Volume 7, Issue 5, Pages 935-939Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cg060849c
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The systematic investigation of supramolecular host systems consisting of a primary amine/carboxylic acids has been performed upon changing the molecular length of the component. The combinations of enantiopure erythro-2-amino-1,2-diphenylethanol (1) and achiral benzoic acid derivatives (2a-e) were found to be effective for the inclusion of 1-phenylethanol derivatives (3a-d) with chiral recognition. X-ray crystallographic analyses revealed that a one-dimensional (1D) helical columnar architecture was commonly constructed in the ternary inclusion crystals. However, there were two types of arrangements of the columns, anti-parallel and parallel, depending on the relative molecular length of 2/3. Similarity in molecular lengths between 2 and 3 resulted in an anti-parallel alignment of the columns, while a parallel alignment was achieved when one of the two components was much longer than the other; the 1D helical columns tend to align in an anti-parallel manner to cancel their dipole; however, the alignment switches to a parallel manner to avoid the formation of large voids between the columns.
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