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Boron dipyrromethene dyes bearing ancillary 2,2′:6′,2″- terpyridine coordination sites

Lookup NU author(s): Emeritus Professor Anthony Harriman, Laura Wildsmith, Beverly Stewart


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Two new boron-dipyrromethene dyes have been synthesised and their photophysical properties have been investigated by steady-state and time-resolved fluorescence spectroscopy. These dyes are equipped with ancillary 2,2′:6′,2″-terpyridine (terpy) residues, attached either at the B centre or at the meso position of the organic framework; in this latter case two ethynylated pyrene units are bound to the B atom. Under most experimental conditions, the absorption and emission spectral properties are typical of this class of dye. Complexation of zinc(II) cations to the terpy units attached at the B centre causes complete extinction of the fluorescence due to intramolecular electron transfer from the excited state dye to the resultant zinc(II) bis-terpy complex. Similar behaviour is noted when the terpy is attached at the meso site, although the rate of electron transfer is slower due to the weaker driving force. A most unusual feature of the pyrene-substituted dye is its facile self association in acetonitrile solution. This results in the reversible formation of a fluorescent associate, believed to be a symmetric dimer, that absorbs and emits to the red of the monomer. Self association is considered to be driven by a solvophobic effect in which the pyrene units seek to minimize surface contact with the surrounding solvent molecules. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Publication metadata

Author(s): Harriman A, Mallon LJ, Stewart B, Ulrich G, Ziessel R

Publication type: Article

Publication status: Published

Journal: European Journal of Organic Chemistry

Year: 2007

Issue: 19

Pages: 3191-3198

Print publication date: 01/01/2007

ISSN (print): 1434-193X

ISSN (electronic): 1099-0690

Publisher: Wiley-Blackwell


DOI: 10.1002/ejoc.200700190


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