Journal
ACS MACRO LETTERS
Volume 4, Issue 9, Pages 1039-1043Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsmacrolett.5b00528
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Funding
- NSF [CHE-1410119]
- University of Pittsburgh
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1410119] Funding Source: National Science Foundation
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A new general synthetic approach to sequenced macromolecules was developed and applied to the synthesis of polymers comprising lactic acid (L), glycolic acid (G), and epsilon-caprolactone (C)-derived monomer units. The new method employs entropy-driven ring-opening metathesis polymerization (ED-ROMP) to prepare copolymers with embedded sequences and controlled molecular weights. Cyclic macromonomer precursors were prepared by ring-closing metathesis of ethylene glycol (Eg)-linked sequenced oligomers bearing terminal olefins. ED-ROMP of the resulting macrocycles using Grubbs' second generation catalyst yielded poly(CL-Eg-LC-Oed), poly(CLL-Eg-LLC-Oed), poly(LGL-Eg-LGL-Oed), and poly(LGL-Eg-LGL-Hed) (Oed = octenedioc acid; Hed = hexenedioc acid). Hydrogenation produced the saturated sequenced copolymers. Molecular weight was well-controlled and could be adjusted by varying the monomer-to-catalyst ratio. M(n)s of 26-60 kDa were obtained (dispersities = 1.1-1.3). The methodology proved general for three different sequences and two olefinic metathesis groups.
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