Abstract
The quadruple click reactions, thiol-ene, copper catalyzed azide-alkyne cycloaddition (CuAAC), Diels-Alder cycloaddition, and nitroxide radical coupling (NRC) reactions were successfully employed for the synthesis of cysteine-functional heterograft brush copolymer. An equimolar mixture of oxanorbornenyl-anthracene (ONB-anthracene), oxanorbornenyl-bromide (ONB-Br), and oxanorbornenyl tosylate (ONB-OTs) was polymerized via ring opening metathesis polymerization (ROMP) using the first generation Grubbs' catalyst in CH 2Cl2 at room temperature to form poly(ONB-anthracene-co- ONB-Br-co-ONB-OTs)10 copolymer as a main backbone. Next, this main backbone was first reacted with N-acetyl-L-cysteine methyl-ester via radical thiol-ene click reaction and then sequentially clicked with a furan protected maleimide-terminated poly(methyl methacrylate) (PMMA20-MI), and 2,2,6,6-tetramethyl-1-piperidinyloxy-terminated poly(ethylene glycol) (PEG 13-TEMPO), alkyne-terminated poly(ε-caprolactone) (PCL 28-alkyne) via Diels-Alder, and NRC/CuAAC reactions, respectively to yield a cysteine-functional poly(ONB-g-PMMA-co-ONB-g-PEG-co-ONB-g-PCL) 10 heterograft brush copolymer.
| Original language | English |
|---|---|
| Pages (from-to) | 1796-1802 |
| Number of pages | 7 |
| Journal | European Polymer Journal |
| Volume | 49 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - Jul 2013 |
Keywords
- Atom transfer radical polymerization (ATRP)
- Copper catalyzed azide-alkyne cycloaddition (CuAAC)
- Diels-Alder cycloaddition Thiol-ene
- Nitroxide radical coupling (NRC)
- Ring opening metathesis polymerization (ROMP)