A short and efficient synthesis of a series of isoprenecarboxylic acid esters and their corresponding polymers is presented. The base-catalyzed eliminative ring opening of anhydromevalonolactone (3) provides isoprenecarboxylic acid (6-H), which was further transformed to the isoprenecarboxylic acid esters. Reversible addition-fragmentation chain-transfer (RAFT) polymerization was used to synthesize high molecular weight (>100 kg mol-1) poly(isoprenecarboxylates) with dispersities of ca. 1.5. The glass transition temperatures (Tg) and entanglement molecular weights (Me) of the poly(isoprenecarboxylates) were determined and showed similar trends to the Tg and Me values for analogous poly(acrylate esters). These new glucose-derived materials could provide a sustainable alternative to poly(acrylates).
|Original language||English (US)|
|Number of pages||4|
|Journal||ACS Macro Letters|
|State||Published - Oct 18 2016|
Bibliographical noteFunding Information:
We thank David W. Giles and Christopher W. Macosko for assistance with rheology studies and Kechun Zhang for providing the mevalonate fermentation broth. Financial support for this research was provided by the Center for Sustainable Polymers at the University of Minnesota, an NSF-supported Center for Chemical Innovation (CHE-1413862). Some of the NMR data were recorded on an instrument purchased with support of the NIH Shared Instrumentation Grant program (S10OD011952).
© 2016 American Chemical Society.