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Novel Molecular Building Blocks Based on the Boradiazaindacene Chromophore: Applications in Fluorescent Metallosupramolecular Coordination Polymers
Author(s) -
Bozdemir Ö. Altan,
Büyükcakir Onur,
Akkaya Engin U.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802538
Subject(s) - bodipy , chromophore , fluorescence , sonogashira coupling , polymerization , chemistry , photochemistry , metal ions in aqueous solution , monomer , supramolecular chemistry , polymer , metal , stoichiometry , polymer chemistry , crystallography , crystal structure , organic chemistry , palladium , physics , quantum mechanics , catalysis
Bright polymers : Fluorescent coordination polymers made up of versatile functionalized bodipy (boron‐dipyrrin) chromophore building blocks, such as that depicted, are described. Polymerization is signaled by changes in fluorescence emission intensity and shifts in peak emission wavelengths.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 1 H 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.