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Preparation and chemical properties of π-conjugated poly(1,10-phenanthroline-3,8-diyl)s with crown ether subunits
Affiliation:1. Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Ratchathewi, Bangkok 10400, Thailand;2. Department of Biochemistry, Faculty of Dentistry, Chulalongkorn University, Henri Dunant Road, Patumwan, Bangkok 10330, Thailand;3. Department of Biochemistry and Center of Excellence in Protein Structure and Function, Faculty of Science, Mahidol University, Rama VI Road, Ratchathewi, Bangkok 10400, Thailand;1. University of Technology and Life Sciences, Faculty of Chemical Technology and Engineering, Seminaryjna 3, 85-326 Bydgoszcz, Poland;2. Nicolaus Copernicus University, Collegium Medicum, Department of Physical Chemistry, Kurpińskiego 5, 85-950 Bydgoszcz, Poland;3. Institute of Physical and Theoretical Chemistry, Wroclaw University of Technology, Wyb. Wyspiańskiego 27, 50-370 Wroclaw, Poland;1. Departamento de Física, Universidade Federal do Paraná, CP 19044, CEP 81531-990 Curitiba, PR, Brazil;2. Department of Applied Chemistry, University of Johannesburg, Doornfontein 2028, South Africa
Abstract:π-Conjugated polymers consisting of 1,10-phenanthroline units and crown ether subunits (Poly-1, Poly-2, and Poly-3) were prepared by dehalogenation polycondensation of the corresponding dibromo monomers using a zero-valent nickel complex as a condensing agent. They were characterized by elemental analysis, 1H NMR and UV–Vis spectroscopies, and cyclic voltammetry (CV). They were partly soluble in CHCl3, and the number average molecular weight of the soluble part of Poly-2, which had 15-crown-5 subunits, was estimated to be 5300. The polymers exhibited UV–Vis peaks at approximately λmax = 360 nm, which was reasonable. Complexation with Ru(bpy)2]2+ and alkaline metal ions made the polymer soluble in organic solvents. The complexation of Ru(bpy)2]2+ to the 1,10-phenanthroline unit proceeded quantitatively, and the Ru(bpy)2]2+ complexes exhibited CV curves characteristic of Ru(N-N)3]2+ complexes.
Keywords:π-Conjugated polymers  Poly(1  10-phenanthroline)  Crown ether  Alkaline metal ions  Ru complex  Organometallic polymerization
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