Optimisation of Self-Immolative Systems: Understanding the Role of the Reporter Group

2019-11-19T15:35:20Z (GMT) by Alexander Gavriel
Stimuli-responsive materials have become significant targets in advance materials as systems of this type offer great potential to perform a variety of functions in a diverse range of applications that span drug delivery (1), biological and chemical sensors (2), diagnostics (3) and degradable polymers (4).

Self-immolative (5) systems are comprised of a stable bond between trigger and reporter group, the stability of which is sensitive to particular agents and environments. Recently, we have described (6) the first examples of selective self-immolative systems triggered by a non-acidic electrophilic species to afford a facile colorimetric visual disclosure of toxic electrophilic alkylating agents.

Through molecular design, we have carried out a systematic study on the reporter group to explore the balance between stability, reactivity and degradation of the self-immolative system. A structure-property relationship was established from the library of stimuli-responsive molecules synthesised, and an improved detector capable of disclosing electrophiles under ambient conditions realised.

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6. A. L. Acton, F. Leroux, A. Feula, K. Melia, M. R. Sambrook, W. Hayes and A. T. Russell, Chem. Commun., 2019, 55, 5219.