So far, studies on signal-amplified responsive synthetic materials using small molecule reagents or self-immolative polymers have been limited due to their challenging synthetic procedures to access reagents or polymers, and issues with background interference. An alternative approach to achieve bio-inspired amplified response in synthetic soft materials is the β-mercaptoethanol (BME) or dithiothreitol (DTT)-mediated amplification cascade based on Meldrum's acid conjugated polymeric materials . This strategy, first described by Anslyn and coworkers , detects thiol signals indirectly via thiolexchange mediated release of BME and its subsequent reaction with a Meldrum's acid-based reagent. Once initiated, the reaction converts one equivalent of BME or DTT to decouple two equivalents of thiol. Using this approach, the authors were able to amplify initial thiol input and convert it to macroscopic material degradation and optical detection. Inspired by these concepts, we sought to develop a new strategy for creating soft polymeric materials that are able to recognize, amplify and translate (bio)chemically relevant signals into global macroscopic material changes, regardless the quantities or molecular size of the applied signal. To realize this, we developed a new molecular approach for signal amplification in aqueous buffer by using allylic substitution of electron deficient allyl acetates with trivalent phosphines as signal amplifiers. This amplifier contains an inactive phosphorous moiety and an electrophilic double bond, which enables nucleophile-triggered substitution, converting the amplifier into a neutral phosphine species. This strategy enables: (i) control over disulfide redox chemistry by using the signal responsive allylic phosphonium ion, capable of direct thiolanalyte recognition and corresponding release of a phosphine species; (ii) coupling of this chemistry to a macroscopic response of a crosslinked hydrogel. Upon signal detection, the gels undergo physical degradation through chemical cascade reactions within the gel matrix.