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Issue 9, 2011
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Catalytic synthesis and post-polymerization functionalization of conjugated polyisoprene

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Abstract

Anionically synthesized polyisoprene (PI) was catalytically isomerized with RuHCl(CO)(PPh3)3 to produce conjugated PI (CPI). Both the reaction time and temperature were varied to control the number of conjugated dienes along the CPI backbone. The same reaction scheme also conjugated polycyclooctadiene, demonstrating the utility of the catalyst to conjugate other olefin-containing polymers. The CPI samples retained their narrow distributions as indicated by size exclusion chromatography (SEC). Small molecules were coupled with CPI through the Diels–Alder click reaction in solution to produce an array of post-polymerization functionalized polymers. In one example, N-2-hydroxyethyl maleimide (HEMI) was coupled to CPI to produce a hydroxylated material. L-Lactide was polymerized from this macroinitiator with both tin(II) octoate (Sn(Oct)2) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) to produce poly(L-lactide) (PLLA) grafted from PI (PI-g-PLLA) with a monomodal SEC distribution at 95 wt% PLLA content.

Graphical abstract: Catalytic synthesis and post-polymerization functionalization of conjugated polyisoprene

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Publication details

The article was received on 01 Apr 2011, accepted on 23 May 2011 and first published on 15 Jun 2011


Article type: Paper
DOI: 10.1039/C1PY00147G
Citation: Polym. Chem., 2011,2, 2062-2067
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    Catalytic synthesis and post-polymerization functionalization of conjugated polyisoprene

    W. M. Gramlich and M. A. Hillmyer, Polym. Chem., 2011, 2, 2062
    DOI: 10.1039/C1PY00147G

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