Self-immolative systems

A self-immolative molecule suitable to be triggered by non-protic electrophilic agents, having structural formula:

• wherein Nu is phosphorus (P), R1 and R2 comprise phenyl functional groups or substituted phenyl functional groups, and releasable portion is a chemical moiety capable of generating a detection/measurable response upon release.

The self-immolative molecule according to claim 29, wherein R6 is NO2, and R4, R6, R7 and R8 are H.

A self-immolative triggered method for interrogating a sample suspected of comprising a non-protic electrophilic agent comprising contacting the sample, in the presence of a mild base, with a self-immolative molecule suitable to be triggered by non-protic electrophilic agents, wherein the self-immolative molecule comprises at least one trigger portion linked to at least one releasable portion via a self-immolative portion, wherein the trigger portion comprises a neutral nucleophile selected from the neutral nucleophiles R3SR1, and —R3PR1R2, wherein R1 and R2 are selected from H, alkyl, aryl, or heteroaryl, S is sulfur, P is phosphorous, and wherein R3 is a chemical moiety capable of undergoing β-elimination and is at least a part of the self-immolative portion, which self immolative portion comprises the functional group CH2OC(O).

The self-immolative triggered method according to C wherein the electrophilic agent is an alkylating agent.

The self-immolative triggered method according to wherein the mild base is diisopropylethamine.