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RSS FeedsMolecules, Vol. 27, Pages 6292: Electrocatalytic Depolymerization of Self-Immolative Poly(Dithiothreitol) Derivatives (Molecules)

 
 

23 september 2022 17:08:41

 
Molecules, Vol. 27, Pages 6292: Electrocatalytic Depolymerization of Self-Immolative Poly(Dithiothreitol) Derivatives (Molecules)
 


We report the use of electrogenerated anthraquinone radical anion (AQ•−) to trigger fast catalytic depolymerization of polymers derived from poly(dithiothreitol) (pDTT)—a self-immolative polymer (SIP) with a backbone of dithiothreitols connected with disulfide bonds and end-capped via disulfide bonds to pyridyl groups. The pDTT derivatives studied include polymers with simple thiohexyl end-caps or modified with AQ or methyl groups by Steglich esterification. All polymers were shown to be depolymerized using catalytic amounts of electrons delivered by AQ•−. For pDTT, as little as 0.2 electrons per polymer chain was needed to achieve complete depolymerization. We hypothesize that the reaction proceeds with AQ•− as an electron carrier (either molecularly or as a pendant group), which transfers an electron to a disulfide bond in the polymer in a dissociative manner, generating a thiyl radical and a thiolate. The rapid and catalytic depolymerization is driven by thiyl radicals attacking other disulfide bonds internally or between pDTT chains in a chain reaction. Electrochemical triggering works as a general method for initiating depolymerization of pDTT derivatives and may likely also be used for depolymerization of other disulfide polymers.


 
50 viewsCategory: Biochemistry, Chemistry, Molecular Biology
 
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