In:
Canadian Journal of Chemistry, Canadian Science Publishing, Vol. 78, No. 6 ( 2000-06-01), p. 723-731
Abstract:
A new H-bonded supramolecular assembly of the diamine-diol family has been obtained from (1R,2R)-1,2-diaminocyclohexane (DAC) and (S)-1-phenyl-1,2-ethanediol (PED). The structure was characterized by single-crystal X-ray analysis and showed the typical architecture of DAC based assemblies, consisting of a three-stranded helicate coiling around a H-bonded core, with a predictable helicity sense determined by the configuration of DAC. The new assembly, while reconfirming the unique role of DAC as a powerful assembler of supramolecular structures, demonstrated that the C 2 symmetry of diol partners employed so far is not essential for assembling helicates, although chirality is. In the case of the adduct between (1R,2R)-1,2-diaminocyclohexane and (2R,3R)-2,3-butanediol, molecular recognition and self-assembly have been shown to take place even in the absence of solvent, in the gas phase, where long crystals were formed by spontaneous organized aggregation of diamine-diol units. A thorough analysis of the results from the present and previous investigations has lead to a deeper understanding of the key features of the diamine-diol molecular code and of the requirements for recognition and assembly.Key words: supramolecular, hydrogen bonding, molecular recognition, self-assembly, diamines, diols.
Type of Medium:
Online Resource
ISSN:
0008-4042
,
1480-3291
Language:
English
Publisher:
Canadian Science Publishing
Publication Date:
2000
detail.hit.zdb_id:
1482256-8
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