Planar chiral asymmetric naphthalenediimide cyclophanes : synthesis, characterization and tunable FRET properties

Gabutti, Sandro and Schaffner, Silvia and Neuburger, Markus and Fischer, Matthias and Schaefer, Gabriel and Mayor, Marcel. (2009) Planar chiral asymmetric naphthalenediimide cyclophanes : synthesis, characterization and tunable FRET properties. Organic and Biomolecular Chemistry, 7 (16). pp. 3222-3229.

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Official URL: http://edoc.unibas.ch/dok/A5259893

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A series of planar chiral asymmetric naphthalenediimide (NDI) cyclophanes (1-4) consisting of two different NDIs interlinked by rigid meta-dimethylenebenzene spacers was synthesized. A modular synthetic strategy based on the dichloro cyclophane 1 as common precursor gave a straightforward access to racemic mixtures of the NDI cyclophane dyes 2-4. In particular the substitution of both chlorine atoms of 1 by tert-butylsulfanyl-, methoxy-and piperidinyl-groups provided racemic mixtures of the fluorescent NDI cyclophane dyes 2, 3 and 4 respectively. Fluorescence spectroscopy revealed chemically tuneable intramolecular FRET properties, as the spectral overlap between the emission of the unsubstituted NDI and the absorption of the core-substituted NDI subunit of the cyclophane could be adjusted by the core substituents. The racemic nature of the samples of cyclophanes 2-4, and in the case of the di-tert-butylsulfanyl functionalized cyclophane 2 the enrichment of both enantiomers, was demonstrated by HPLC using a chiral stationary phase. The solid state structure of 2 was determined by X-ray analysis. A periodic arrangement of both enantiomers of the planar chiral cyclophane 2 in pillars such that NDI- and 2,6-core substituted NDI chromophores alternate periodically was observed.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Molecular Devices and Materials (Mayor)
UniBasel Contributors:Mayor, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:05 Apr 2017 14:05
Deposited On:22 Mar 2012 14:07

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