Issue 6, 2013

High-density and hetero-functional group engineering of segmented hyperbranched polymersvia click chemistry

Abstract

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 ∼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.

Graphical abstract: High-density and hetero-functional group engineering of segmented hyperbranched polymers via click chemistry

Supplementary files

Article information

Article type
Paper
Submitted
10 Nov 2012
Accepted
27 Nov 2012
First published
28 Nov 2012

Polym. Chem., 2013,4, 1774-1787

High-density and hetero-functional group engineering of segmented hyperbranched polymers via click chemistry

S. Li, J. Han and C. Gao, Polym. Chem., 2013, 4, 1774 DOI: 10.1039/C2PY20951A

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