Journal
POLYMER CHEMISTRY
Volume 4, Issue 6, Pages 1774-1787Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2py20951a
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Funding
- National Natural Science Foundation of China [20974093, 51173162]
- Qianjiang Talent Foundation of Zhejiang Province [2010R10021]
- Fundamental Research Funds for the Central Universities [2011QNA4029]
- Research Fund for the Doctoral Program of Higher Education of China [20100101110049]
- Zhejiang Provincial Natural Science Foundation of China [R4110175]
- China Postdoctoral Science Foundation [20100471707]
- China Postdoctoral Science Special Foundation [201104716]
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A new kind of segmented hyperbranched polymers (SHPs), hyperbranched poly(glycidyl methacrylate)s (HPGMAs), were synthesized via reversible addition-fragmentation chain transfer self-condensing vinyl polymerization (RAFT-SCVP). HPGMAs were efficiently functionalized on the whole scaffold via a collection of click chemistries, including the azidation of oxirane, thiol-epoxy click chemistry, thiol-ene click chemistry, copper-catalyzed azide-alkyne cycloaddition (CuAAC), and Menschutkin chemistry, affording SHPs with hetero-functional groups including hydroxyl + azide, dual hydroxyl, triple hydroxyl, hydroxyl + tertiary amine, hydroxyl + alkene, hydroxyl + carboxyl, alkene + azide, alkyne + azide, hydroxyl + alkyne, dual hydroxyl + alkene etc., all at similar to 100% conversion. Thiol-epoxy + thiol-ene sequential dual click and thiol-epoxy + Menschutkin chemistry + CuAAC triple click strategies were presented, making functional group transformation readily accessible. Hydrophilic dendritic brushes, hydrophobic dendritic brushes and amphiphilic dendritic hetero-brushes were synthesized. Esterification of SHP containing hydroxy and azido groups with 1-pyrenebutyric acid yielded clickable fluorescent macromolecules, which showed a very strong excimer emission.
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