ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 2,7-diazapyrenium group (DAP2+) combines the features of pyrene, of methylviologen, and of nucleicacid intercalators and may thus present a variety of interesting properties. The cations 1 and 2 and the bis-diazapyrenium species 3 have been synthesized and shown to bind molecular anions like aromatic polycarboxylates, giving rise to pronounced shifts of 1H-NMR signals, modifications of UV/VIS absorption spectra, and quenching of fluorescence. The complexes formed probably have a face-to-face structure, and their stability constants are remarkably high, in particular for the bis-diazapyrenium cation 3 which is susceptible to form intercalative chelate complexes such as 9(log Ks ≈ 3 for 1, up to ca. 7 or more for 3a). Neutral molecules like adenine are also bound, but much less strongly. Visible-light irradiation of Me2DAP2+ (1) in presence of various electron donors, such as EDTA, gives the reduced species Me2DAP+ wich has been characterized by UV/VIS and ESR spectroscopy. The results indicate that Me2DAP2+ (1) functions as a methylviologen analogue, photoactive in visible light. Thus 2,7-diazapyrenium cations are attractive subunits for incorporation into macropolycyclic structures to give photo- and electroactive receptor molecules.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19870700102
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