Neutral π - associated porphyrin [2]catenanes

Title
Neutral π - associated porphyrin [2]catenanes
Publication Date
2003
Author(s)
Gunter, Maxwell John
Farquhar, Sandra
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
Royal Society of Chemistry
Place of publication
United Kingdom
DOI
10.1039/b307383a
UNE publication id
une:1391
Abstract
A series of neutral porphyrin-containing catenanes has been synthesised, consisting of a zinc porphyrin strapped by apolyethylene glycol chain containing four or six ethylenoxy-units and incorporating a central naphthoquinol unit,interlinked with a naphthalene diimide macrocycle. The napthalene diimide precursor units exhibit only weakbinding with the strapped porphyrins (K[a] between 8 and 0.02 M⁻¹), but good yields of the catenanes were obtained byGlaser coupling of the alkynyl napthalene diimide precursors in the presence of the porphyrins. Structures andsolution conformations were determined by mass spectral and detailed ¹H NMR studies. For the longer strappedporphyrins, the diimide macrocycle rotates around the central naphthoquinol unit at 420–450 times per second, whilerotation is virtually prevented in the tighter strapped derivatives. A second dynamic process occurring in both sets ofcatenanes and described as ‘yawing’ leads to inequivalence in the naphthalene moieties. UV-Visible spectra indicatecharge transfer interactions and electronic communication between the two components of the catenane.
Link
Citation
Organic & Biomolecular Chemistry, 1(0), p. 3450-3457
ISSN
1477-0539
1477-0520
Start page
3450
End page
3457

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