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Supramolecular chemistry of monochiral naphthalenediimides.

Authors
Type
Published Article
Journal
Organic & Biomolecular Chemistry
1477-0520
Publisher
The Royal Society of Chemistry
Publication Date
Volume
9
Issue
21
Pages
7547–7553
Identifiers
DOI: 10.1039/c1ob06147j
PMID: 21946946
Source
Medline

Abstract

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.

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