Post-Polymerization Functionalization Approach for Highly Water-Soluble Well-Defined Regioregular Head-to-Tail Glycopolythiophenes
Autor: | Cuihua Xue, Fen-Tair Luo, Haiying Liu |
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Rok vydání: | 2007 |
Předmět: | |
Zdroj: | Macromolecules. 40:6863-6870 |
ISSN: | 1520-5835 0024-9297 |
Popis: | Two bromide-bearing regioregular head-to-tail polythiophenes (polymers 1 and 3) were prepared by using Grignard metathesis method to polymerize 2,5-dibromo-3-bromohexylthiophene (2) and 2,5-dibromo-3-(11-bromo-3,6,9-trioxa-1-undecoxy)thiophene (7), respectively. Well-defined regioregular head-to-tail glycopolythiophenes were prepared through post-polymerization functionalization approach by treating the bromide-bearing polythiophenes with 1-thiolethyl-α-d-mannose tetraacetate (3a) or 1-thiol-β-d-glucose tetraacetrate (3b) in THF solution with a basic condition, respectively, and followed by sequential deacetylation under Zemplen conditions in methanol and methylene chloride containing sodium methoxide at room temperature. Glycopolythiophenes (polymers C and D) with hydrophilic tetra(ethylene glycol) as tethered spacers between the polymer backbone and carbohydrate residues are highly water-soluble while glycopolythiophenes (polymers A and B) with hydrophobic hexyl tethered spacers are completely insoluble... |
Databáze: | OpenAIRE |
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