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Multicomponent Reactions with a Convertible Isocyanide: Efficient and Versatile Grafting of ADMET‐Derived Polymers
Author(s) -
Kreye Oliver,
Trefzger Carsten,
Sehlinger Ansgar,
Meier Michael A. R.
Publication year - 2014
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/macp.201400187
Subject(s) - chemistry , isocyanide , monomer , polymerization , gel permeation chromatography , polymer chemistry , amide , polymer , triphosgene , metathesis , nucleophile , organic chemistry , combinatorial chemistry , catalysis , phosgene
The Ugi four‐component reaction (Ugi‐4CR) and the Passerini three‐component reaction (Passerini‐3CR) are applied for α,ω‐diene monomer synthesis using a convertible isocyanide. These monomers are polymerized using acyclic diene metathesis polymerization (ADMET), followed by hydrogenation of the double bonds and conversion of the isocyanide‐derived moieties to highly reactive indolyl amides under mild acidic conditions. Subsequently, several post‐polymerization modification reactions of these indolyl‐amide‐containing ADMET polymers are investigated using different nucleophiles. Under elimination of indole, side‐chain modifications to carboxylic acids, esters, secondary and tertiary amides, and thioesters are shown, leading to diversely substituted polymers exhibiting different properties. Moreover, multicomponent reactions are also used for further modifications. All the obtained polymers are carefully characterized by NMR, gel‐permeation chromatography (GPC), DSC, and IR measurements.