DNA Triplex-Mediated Assembly of Polyaromatic Chromophores

Authors

  • Sarah M. Biner,

    1. Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, (phone: +41 31 631 4382)
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  • Robert Häner

    Corresponding author
    1. Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, (phone: +41 31 631 4382)
    • Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, (phone: +41 31 631 4382)
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Abstract

The synthesis and characterization of intramolecular triple-helical DNA structures containing polyaromatic pyrene and perylene (perylenetetracarboxylic acid diimide, PDI) building blocks are presented. Two 1,8-dialkynylpyrene units are located in the Watson[BOND]Crick stem of the construct, while a PDI or a natural thymidine is present in the Hoogsteen strand. The triple helical structures were investigated by UV/VIS absorbance, fluorescence spectroscopy, and circular dichroism (CD) measurements. The folding of the intramolecular triple helix can be monitored by changes in the vibronic transition ratios, as well as by a change in the alkynylpyrene fluorescence (monomer vs. excimer). It is shown that thymine in the third strand has a pronounced influence on the interaction and, thus, on the fluorescence properties of two pyrene building blocks.

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