The design of self-immolative systems has been based upon a stable bond between trigger and reporter groups, the stability of which is sensitive to particular agents and environments. Chemically specific triggers have been realised for a diverse range of applications spanning drug delivery, biological and chemical sensors, diagnostics and degradable polymers. ‘Classical’ self-immolative chemistries operate by activation or deprotection of the trigger group by nucleophiles (<i>e.g.</i> fluoride, RSH) to render the immolative unit labile via generation of an electron rich, nucleophilic centre that then initiates a cascade of electrons and culminates in the release of the reporter group. To date, only limited use of self-immolative linkers in the disclosure of electrophilic species such as chemical warfare agents (CWAs), fumigants, pesticides, pharmaceuticals and other environmental hazards, has been reported and that by the vicarious generation of a nucleophile to trigger the self-immolative pathway. The challenge in generating a colorimetric disclosure system for reagents of this reactivity type under ambient conditions is to create a triggering system that responds to an electrophilic reagent in such a way as to allow indirect generation of a nucleophilic electron-rich centre in the trigger event. In this presentation, we report how we met this challenge by designing a series of disclosure molecules (see Figure 1) that represent the first examples of selective self-immolative systems triggered by a non-acidic electrophilic species such as methyl, allyl and benzylic halides as distinct from a proton, for the avoidance of false positive results. These systems provide a visual colorimetric response to such electrophiles, following exposure to mild, basic conditions, without the need for analytical instrumentation and thus there is great potential for the use of these reagents for the visual disclosure of toxic electrophilic alkylating agents.

Self-immolative systems for the disclosure of reactive electrophilic alkylating agents

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.