Synthesis and Closed-Loop Recycling of Self-Immolative Poly(dithiothreitol)

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Synthesis and Closed-Loop Recycling of Self-Immolative Poly(dithiothreitol). / Pal, Sunirmal; Sommerfeldt, Andreas; Davidsen, Maiken Berglund; Hinge, Mogens; Pedersen, Steen Uttrup; Daasbjerg, Kim.

In: Macromolecules, Vol. 53, No. 12, 06.2020, p. 4685-4691.

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Pal, Sunirmal ; Sommerfeldt, Andreas ; Davidsen, Maiken Berglund ; Hinge, Mogens ; Pedersen, Steen Uttrup ; Daasbjerg, Kim. / Synthesis and Closed-Loop Recycling of Self-Immolative Poly(dithiothreitol). In: Macromolecules. 2020 ; Vol. 53, No. 12. pp. 4685-4691.

Bibtex

@article{5eaae84cd4674cd587c02fb2f656a3ec,
title = "Synthesis and Closed-Loop Recycling of Self-Immolative Poly(dithiothreitol)",
abstract = "Self-immolative polymers (SIPs) are promising members of the emerging class6 of recyclable polymers with the ability to end-to-end depolymerize to their monomers.7 Unfortunately, SIPs are often synthesized by cumbersome procedures at low temperatures in8 protected atmosphere. In this study, a SIP with a novel poly(disulfide) backbone is introduced,9 using DL-dithiothreitol (DTT) as the monomer. Remarkably, poly(DTT) can be produced by10 solid-state polymerization in a robust and easily scalable process by mechanically mixing DTT11 with 2,2′-dithiodipyridine as the end-capping agent. The new polymer possesses good thermal12 and chemical stabilities, but once its depolymerization is triggered, this proceeds smoothly13 within minutes to afford cyclic DTT because of a favorable intramolecular back-biting thiol−14 disulfide exchange reaction in the polymer backbone. As a proof of concept, the cyclic DTT15 waste was recovered, reduced to DTT monomer, and repolymerized in a closed-loop approach.",
author = "Sunirmal Pal and Andreas Sommerfeldt and Davidsen, {Maiken Berglund} and Mogens Hinge and Pedersen, {Steen Uttrup} and Kim Daasbjerg",
year = "2020",
month = jun,
doi = "10.1021/acs.macromol.0c00861",
language = "English",
volume = "53",
pages = "4685--4691",
journal = "Macromolecules",
issn = "0024-9297",
publisher = "AMER CHEMICAL SOC",
number = "12",

}

RIS

TY - JOUR

T1 - Synthesis and Closed-Loop Recycling of Self-Immolative Poly(dithiothreitol)

AU - Pal, Sunirmal

AU - Sommerfeldt, Andreas

AU - Davidsen, Maiken Berglund

AU - Hinge, Mogens

AU - Pedersen, Steen Uttrup

AU - Daasbjerg, Kim

PY - 2020/6

Y1 - 2020/6

N2 - Self-immolative polymers (SIPs) are promising members of the emerging class6 of recyclable polymers with the ability to end-to-end depolymerize to their monomers.7 Unfortunately, SIPs are often synthesized by cumbersome procedures at low temperatures in8 protected atmosphere. In this study, a SIP with a novel poly(disulfide) backbone is introduced,9 using DL-dithiothreitol (DTT) as the monomer. Remarkably, poly(DTT) can be produced by10 solid-state polymerization in a robust and easily scalable process by mechanically mixing DTT11 with 2,2′-dithiodipyridine as the end-capping agent. The new polymer possesses good thermal12 and chemical stabilities, but once its depolymerization is triggered, this proceeds smoothly13 within minutes to afford cyclic DTT because of a favorable intramolecular back-biting thiol−14 disulfide exchange reaction in the polymer backbone. As a proof of concept, the cyclic DTT15 waste was recovered, reduced to DTT monomer, and repolymerized in a closed-loop approach.

AB - Self-immolative polymers (SIPs) are promising members of the emerging class6 of recyclable polymers with the ability to end-to-end depolymerize to their monomers.7 Unfortunately, SIPs are often synthesized by cumbersome procedures at low temperatures in8 protected atmosphere. In this study, a SIP with a novel poly(disulfide) backbone is introduced,9 using DL-dithiothreitol (DTT) as the monomer. Remarkably, poly(DTT) can be produced by10 solid-state polymerization in a robust and easily scalable process by mechanically mixing DTT11 with 2,2′-dithiodipyridine as the end-capping agent. The new polymer possesses good thermal12 and chemical stabilities, but once its depolymerization is triggered, this proceeds smoothly13 within minutes to afford cyclic DTT because of a favorable intramolecular back-biting thiol−14 disulfide exchange reaction in the polymer backbone. As a proof of concept, the cyclic DTT15 waste was recovered, reduced to DTT monomer, and repolymerized in a closed-loop approach.

U2 - 10.1021/acs.macromol.0c00861

DO - 10.1021/acs.macromol.0c00861

M3 - Journal article

VL - 53

SP - 4685

EP - 4691

JO - Macromolecules

JF - Macromolecules

SN - 0024-9297

IS - 12

ER -