Issue 14, 2008

Porphyrin–naphthodiimide interactions as a structural motif in foldamers and supramolecular assemblies

Abstract

π–π Stacking interactions between electron deficient naphthalenediimides (NDI) and electron-rich porphyrins (POR) leading to charge transfer are shown to be prevalent in linked NDI–POR and POR–NDI–POR structures. For flexibly-linked systems, intramolecular interactions lead to S-shaped foldamers in solution, whereas intermolecular association is predominant in more rigid systems. The foldamer structures can be interrupted by competing aromatic solvents, by six-coordination of metallated porphyrin derivatives, by protonation of the free base porphyrin in non-metallated structures, and in facially sterically hindered porphyrins.

Graphical abstract: Porphyrin–naphthodiimide interactions as a structural motif in foldamers and supramolecular assemblies

Supplementary files

Article information

Article type
Paper
Submitted
14 Mar 2008
Accepted
16 Apr 2008
First published
16 May 2008

Org. Biomol. Chem., 2008,6, 2534-2543

Porphyrin–naphthodiimide interactions as a structural motif in foldamers and supramolecular assemblies

Z. Merican, K. D. Johnstone and M. J. Gunter, Org. Biomol. Chem., 2008, 6, 2534 DOI: 10.1039/B804267E

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