Polylactide-polythiophene-polylactide triblock copolymers

Bryan W. Boudouris; C. Daniel Frisbie; Marc A. Hillmyer

doi:10.1021/ma1002134

Polylactide-polythiophene-polylactide triblock copolymers

Bryan W. Boudouris, C. Daniel Frisbie, Marc A. Hillmyer

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39 Scopus citations

Abstract

The synthesis of polylactide-b-polythiophene-b-polylactide block copolymers (PLA-PT-PLA) by the controlled polymerization of D,L-lactide from hydroxyl-terminated telechelic polythiophenes (HO-PT-OH) was reported. The end groups of regioregular, regiorandom, and copolymerized P3ATs were converted into nonfunctionalized end groups (PT) through the use of the halogen-magnesium exchange reaction followed by hydrolysis. PT polymers were converted to the bis-aldehyde polymers (HCO-PT-COH) using a Vilsmeier transformation and were subsequently reduced with LiAlH₄ to the hydroxyl-terminated polythiophenes. The resonance associated with the methylene end group protons at δ ≊ 4.8 ppm in HO-PT-OH was not observed upon PLA addition presumably because this resonance had approximately the same chemical shift as one of the main chain PLA protons.

Original language	English (US)
Pages (from-to)	3566-3569
Number of pages	4
Journal	Macromolecules
Volume	43
Issue number	7
DOIs	https://doi.org/10.1021/ma1002134
State	Published - Apr 13 2010

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title = "Polylactide-polythiophene-polylactide triblock copolymers",

abstract = "The synthesis of polylactide-b-polythiophene-b-polylactide block copolymers (PLA-PT-PLA) by the controlled polymerization of D,L-lactide from hydroxyl-terminated telechelic polythiophenes (HO-PT-OH) was reported. The end groups of regioregular, regiorandom, and copolymerized P3ATs were converted into nonfunctionalized end groups (PT) through the use of the halogen-magnesium exchange reaction followed by hydrolysis. PT polymers were converted to the bis-aldehyde polymers (HCO-PT-COH) using a Vilsmeier transformation and were subsequently reduced with LiAlH4 to the hydroxyl-terminated polythiophenes. The resonance associated with the methylene end group protons at δ ≊ 4.8 ppm in HO-PT-OH was not observed upon PLA addition presumably because this resonance had approximately the same chemical shift as one of the main chain PLA protons.",

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AU - Boudouris, Bryan W.

AU - Frisbie, C. Daniel

AU - Hillmyer, Marc A.

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N2 - The synthesis of polylactide-b-polythiophene-b-polylactide block copolymers (PLA-PT-PLA) by the controlled polymerization of D,L-lactide from hydroxyl-terminated telechelic polythiophenes (HO-PT-OH) was reported. The end groups of regioregular, regiorandom, and copolymerized P3ATs were converted into nonfunctionalized end groups (PT) through the use of the halogen-magnesium exchange reaction followed by hydrolysis. PT polymers were converted to the bis-aldehyde polymers (HCO-PT-COH) using a Vilsmeier transformation and were subsequently reduced with LiAlH4 to the hydroxyl-terminated polythiophenes. The resonance associated with the methylene end group protons at δ ≊ 4.8 ppm in HO-PT-OH was not observed upon PLA addition presumably because this resonance had approximately the same chemical shift as one of the main chain PLA protons.

AB - The synthesis of polylactide-b-polythiophene-b-polylactide block copolymers (PLA-PT-PLA) by the controlled polymerization of D,L-lactide from hydroxyl-terminated telechelic polythiophenes (HO-PT-OH) was reported. The end groups of regioregular, regiorandom, and copolymerized P3ATs were converted into nonfunctionalized end groups (PT) through the use of the halogen-magnesium exchange reaction followed by hydrolysis. PT polymers were converted to the bis-aldehyde polymers (HCO-PT-COH) using a Vilsmeier transformation and were subsequently reduced with LiAlH4 to the hydroxyl-terminated polythiophenes. The resonance associated with the methylene end group protons at δ ≊ 4.8 ppm in HO-PT-OH was not observed upon PLA addition presumably because this resonance had approximately the same chemical shift as one of the main chain PLA protons.

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Polylactide-polythiophene-polylactide triblock copolymers

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