Supramolecular chemistry of monochiral naphthalenediimides

Three new N-desymmetrised naphthalenediimides (NDIs) are described, each containing one chiral and one achiral centre. The ability of such 'monochiral' NDIs to self-assemble into hydrogen-bonded helical nanotubes, to act as a sergeant in a 'sergeants-and-soldiers' system and to f...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2011-11, Vol.9 (21), p.7547-7553
Main Authors: Anderson, Tom W, Pantoş, G Dan, Sanders, Jeremy K M
Format: Article
Language:English
Subjects:
Imides - chemical synthesis
Imides - chemistry
Macromolecular Substances - chemical synthesis
Macromolecular Substances - chemistry
Molecular Structure
Naphthalenes - chemical synthesis
Naphthalenes - chemistry
Stereoisomerism
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Summary:Three new N-desymmetrised naphthalenediimides (NDIs) are described, each containing one chiral and one achiral centre. The ability of such 'monochiral' NDIs to self-assemble into hydrogen-bonded helical nanotubes, to act as a sergeant in a 'sergeants-and-soldiers' system and to form a hexameric receptor for C(70) was examined. Small differences at the achiral centre were found to have significant effects on the supramolecular properties of the NDI. All three new NDIs form nanotubes that bind C(60), but with different efficiencies, and one is a better sergeant than any of the dichiral NDIs investigated to date.
ISSN:1477-0520
1477-0539
DOI:10.1039/c1ob06147j