Synthesis and Photophysical Properties of a Series of Novel Porphyrin Dendrimers Containing Organoiron Complexes View Full Text


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Article Info

DATE

2019-03

AUTHORS

Mosa Alsehli, Shaya Y. Al-Raqa, Inan Kucukkaya, Paul R. Shipley, Brian D. Wagner, Alaa S. Abd-El-Aziz

ABSTRACT

This article is focused on the design and photophysical properties of a series of novel porphyrin and metalloporphyrin dendrimers containing cationic η6-chloroarene-η5-cyclopentadienyliron(II) complexes functionalized with naphthalene and capped with ferrocene. The incorporation of cationic η6-chloroarene-η5-cyclopentadienyliron moieties into the dendrimer structures enhances solubility, and facilitates nucleophilic aromatic substitution and addition reactions due to the intense electron-withdrawing ability of the iron center. Divergent approaches were employed to yield highly symmetrical branched materials, with interesting and potentially useful properties. The preparation of these dendrimers was achieved via metal-mediated nucleophilic aromatic substitutions and Steglich esterifications. These dendrimers and their precursors were characterized through nuclear magnetic resonance spectroscopy, infrared spectroscopy, and UV–Visible and fluorescence spectroscopy. Substitution on the porphyrin core with various side chains and terminal functional groups and chromophores had little impact on the porphyrin emission properties, allowing for a wide variety of fluorescent macromolecules to be prepared which retain this characteristic emission. Also, the presence or absence of the organopyrene moieties also had little effect on the emission from these compounds. Complexation of a metal cation, such as Zn2+, by these compounds, did however result in a significant blue shift in the observed fluorescence; this interesting result has the potential for applications in the development of fluorescent-based cation sensors. More... »

PAGES

628-641

References to SciGraph publications

  • 2014-12. Dendrimers: synthesis, applications, and properties in NANOSCALE RESEARCH LETTERS
  • 2005-09. Hyperbranched Polymers Containing Cyclopentadienyliron Complexes in JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS
  • 2004-12. First Example of Benzothiazole Azo Dyes Containing Cyclopentadienyliron Polynorbornene Macromolecules in JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS
  • 2012-04. Electron-transfer processes in dendrimers and their implication in biology, catalysis, sensing and nanotechnology in NATURE CHEMISTRY
  • 2007-10-25. Genealogically directed synthesis: Starburst/cascade dendrimers and hyperbranched structures in SUPRAMOLECULAR CHEMISTRY I — DIRECTED SYNTHESIS AND MOLECULAR RECOGNITION
  • 2010-09. Design of Star-Shaped Organoiron Oligomers with Azo Dye Bridges in JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/s10904-018-1019-0

    DOI

    http://dx.doi.org/10.1007/s10904-018-1019-0

    DIMENSIONS

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