Complementary electrostatic interaction between the zwitterionic merocyanine and dipolar molecules has emerged as a common strategy for reversibly structural conversion of spiropyrans. Herein, we report a concept-new approach for thermal switching of a spiropyran that is based on simultaneous nucleophilic-substitution reaction and electrostatic interaction. The nucleophilic-substitution at spiro-carbon atom of a spiropyran is promoted due to electron-deficient interaction induced by 6- and 8-nitro groups, which is responsible for the isomerization of the spiropyran by interacting with thiol-containing amino acids. Further, the electrostatic interaction between the zwitterionic merocyanine and the amino acids would accelerate the structural conversion. As proof-of-principle, we outline the route to glutathione (GSH)-induced ring-opening of 6,8-dinitro-1',3',3'-trimethylspiro [2H-1-benzopyran-2,2'-indoline] (1) and its application for rapid and sensitive colorimetric detection of GSH. In ethanol-water (1:99, v/v) solution at pH 8.0, the free 1 exhibited slight-yellow color, but the color changed clearly from slight-yellow to orange-yellow when GSH was introduced into the solution. Ring-opening rate of 1 upon accession of GSH in the dark is 0.45 s(-1), which is 4 orders of magnitude faster in comparison with the rate of the spontaneous thermal isomerization. The absorbance enhancement of 1 at 480 nm was in proportion to the GSH concentration of 2.5 × 10(-8)-5.0 × 10(-6) M with a detection limit of 1.0 × 10(-8) M. Furthermore, due to the specific chemical reaction between the probe and target, color change of 1 is highly selective for thiol-containing amino acids; interferences from other biologically active amino acids or anions are minimal.

A chromogenically reversible, mechanochromic pressure sensor is integrated into a mininvasive surgical grasper compatible with the da Vinci robotic surgical system. The sensorized effector, also featuring two soft‐material jaws, encompasses a mechanochromic polymeric inset doped with functionalized spiropyran (SP) molecule, designed to activate mechanochromism at a chosen pressure and providing a reversible color change. Considering such tools are systematically in the visual field of the operator during surgery, color change of the mechanochromic effector can help avoid tissue damage. No electronics is required to control the devised visual feedback. SP‐doping of polydimethylsiloxane (2.5:1 prepolymer/curing agent weight ratio) permits to modulate the mechanochromic activation pressure, with lower values around 1.17 MPa for a 2% wt. SP concentration, leading to a shorter chromogenic recovery time of 150 s at room temperature (25 °C) under green light illumination. Nearly three‐times shorter recovery time is observed at body temperature (37 °C). To the best of knowledge, this study provides the first demonstration of mechanochromic materials in surgery, in particular to sensorize unpowered surgical effectors, by avoiding dramatic increases in tool complexity due to additional electronics, thus fostering their application. The proposed sensing strategy can be extended to further tools and scopes.

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