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Updated: May 29, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Supramolecular chemistry of monochiral naphthalenediimides
Tom W Anderson1, G Dan Pantoş, Jeremy K M Sanders
1University Chemical Laboratory, University of Cambridge, Lensfield Rd., Cambridge, UK CB2 1EW.
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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