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Hydroxyindanone based polymers, 1. Synthesis of monomers, their complexing and polymerisation behaviour
Author(s) -
Hallensleben Manfred L.,
Mödler Michael
Publication year - 1998
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(19980101)199:1<71::aid-macp71>3.0.co;2-g
Subject(s) - chemistry , monomer , polymer chemistry , differential scanning calorimetry , styrene , gel permeation chromatography , polymer , polymerization , nuclear magnetic resonance spectroscopy , molecule , copolymer , organic chemistry , physics , thermodynamics
Based on the elementary constituent 4‐bromo‐7‐hydroxy‐3‐methylindan‐1‐one ( 1b ), the monomers 7‐hydroxy‐3‐methyl‐4‐vinylindan‐1‐one ( 1 ), 7‐hydroxy‐3‐methyl‐4‐vinylindan‐1‐( N ‐phenylimine) ( 2 ) and 7‐hydroxy‐3‐methyl‐4‐vinylindan‐1‐thione ( 3 ) were prepared. The monomers were characterised via common techniques such as nuclear magnetic resonance ( 1 H NMR and 13 C NMR), infrared (IR), mass spectroscopy ( MS ), high resolution mass spectroscopy (HRMS) and differential scanning calorimetry (DSC). Homo‐ and copolymerisation succeeded by free radical polymerisation in solution. The resulting polymers were examined by gel permeation chromatography (GPC) and the copolymerisation behaviour of 7‐hydroxy‐3‐methyl‐4‐vinylindan‐1‐one and 7‐hydroxy‐3‐methyl‐4‐vinylindan‐1‐( N ‐phenylimine) towards styrene and N,N ‐dimethylacrylamide was investigated. The chelating ability towards several metal ions was tested with non‐polymerisable model substances using UV/Vis spectroscopy. The molecules show selectivity towards the ionic radii of metal ions due to fixed ligands by the condensed ring system. Variation of the coordinating atom (O,N,S) selects metal ions corresponding to the Lewis hard and soft acids and bases concept.