Synthesis of Self‑Immolative Polymers

Students: Maiken Berglund Davidsen

Supervisors: Kim Daasbjerg and Steen Uttrup Pedersen


Project description: Self-immolative polymers are classified as polymers with the unique degradability property of head‑to‑tail depolymerization upon specific external stimuli.  In this project we will synthesize a short chained self-immolative polymer from one of the simplest precursors available, i.e. dithiothreitol (DTT)


Aim/Hypothesis: By carrying out the polymerization process at low temperature and let 2,2ˈ‑dipyridyl disulfide serve as endcapping agent, we believe that the synthesis of self-immolative DTT can be accomplished for the first time

Method: Synthesis using DTT and 2,2ˈ‑dipyridyl disulfide in N,N‑dimethylformamide is expected to produce poly(DTT). To be successful one probably needs to lower the temperature considerably. The advantage is that the synthesis of poly(DTT) will be much less sensitive to moisture and adventurous impurities compared with other self‑immolative systems, and, therefore, can be prepared outside a glovebox. The determination of the number of repeating units will be done by NMR. Likewise, NMR can be used in the study of the degradation mechanism.

Perspectives: The promises of self‑immolative polymers are great, in that they may find use as environmentally friendly plastics and biodegradable polymeric materials that are produced from renewable nonpetroleum resources. Furthermore, at the end of their product life they can be degraded into reusable nontoxic intermediates.

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