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

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Self-immolative polymers (SIPs) are promising members of the emerging class
6 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 in
8 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 by
10 solid-state polymerization in a robust and easily scalable process by mechanically mixing DTT
11 with 2,2′-dithiodipyridine as the end-capping agent. The new polymer possesses good thermal
12 and chemical stabilities, but once its depolymerization is triggered, this proceeds smoothly
13 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 DTT
15 waste was recovered, reduced to DTT monomer, and repolymerized in a closed-loop approach.
Original languageEnglish
JournalMacromolecules
Volume53
Issue12
Pages (from-to)4685-4691
Number of pages7
ISSN0024-9297
DOIs
Publication statusPublished - Jun 2020

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