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

Research output: Contribution to journal › Article › peer-review

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

Publisher link

10.1021/ma1002134

Find It

Find It at U of M Libraries

Cite this

@article{613db4ca1757489db914f153d460e4b9,

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.",

author = "Boudouris, {Bryan W.} and Frisbie, {C. Daniel} and Hillmyer, {Marc A.}",

year = "2010",

month = apr,

day = "13",

doi = "10.1021/ma1002134",

language = "English (US)",

volume = "43",

pages = "3566--3569",

journal = "Macromolecules",

issn = "0024-9297",

publisher = "American Chemical Society",

number = "7",

}

TY - JOUR

T1 - Polylactide-polythiophene-polylactide triblock copolymers

AU - Boudouris, Bryan W.

AU - Frisbie, C. Daniel

AU - Hillmyer, Marc A.

PY - 2010/4/13

Y1 - 2010/4/13

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.

UR - http://www.scopus.com/inward/record.url?scp=77951543929&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77951543929&partnerID=8YFLogxK

U2 - 10.1021/ma1002134

DO - 10.1021/ma1002134

M3 - Article

AN - SCOPUS:77951543929

SN - 0024-9297

VL - 43

SP - 3566

EP - 3569

JO - Macromolecules

JF - Macromolecules

IS - 7

ER -

Polylactide-polythiophene-polylactide triblock copolymers

Abstract

Publisher link

Find It

Other files and links

Fingerprint

Cite this