Novel Molecular Building Blocks Based on the Boradiazaindacene Chromophore: Applications in Fluorescent Metallosupramolecular Coordination Polymers


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Bozdemir O. A. , Buyukcakir O., AKKAYA E. U.

CHEMISTRY-A EUROPEAN JOURNAL, vol.15, no.15, pp.3830-3838, 2009 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 15 Issue: 15
  • Publication Date: 2009
  • Doi Number: 10.1002/chem.200802538
  • Title of Journal : CHEMISTRY-A EUROPEAN JOURNAL
  • Page Numbers: pp.3830-3838
  • Keywords: coordination polymers, dyes/pigments, polymerization, self-assembly, Sonogashira coupling, RESONANCE ENERGY-TRANSFER, SUPRAMOLECULAR POLYMERS, BODIPY DYES, PHOTODYNAMIC THERAPY, TERPYRIDINE, CHEMISTRY, EFFICIENT, BORON, ION, ARCHITECTURES

Abstract

We designed and synthesized novel boradiazaindacene (Bodipy) derivatives that are appropriately functionalized for metal-ion-mediated supramolecular polymerization. Thus, ligands for 2-terpyridyl-, 2,6-terpyridyl-. and bipyridyl-functionalized Bodipy dyes were synthesized through Sonogashira couplings. These fluorescent building blocks are responsive to metal ions in a stoichiometry-dependent manner. Octahedral coordinating metal ions such as Zn-II result in polymerization at a stoichiometry corresponding to two terpyridyl ligands to one Zn-II ion. However, at increased metal ion concentrations, the dynamic equilibria are re-established in such a way that the monomeric metal complex dominates. The position of equilibria can easily be monitored by H-1 NMR and fluorescence spectroscopies. As expected, although open-shell Fe-II ions form similar complex structures, these cations quench the fluorescence emission of all four functionalized Bodipy ligands.