The Power of Action Plots: Unveiling Reaction Selectivity of Light‐Stabilized Dynamic Covalent Chemistry

Exploiting the optimum wavelength of reactivity for efficient photochemical reactions has been well‐established based on the development of photochemical action plots. We herein demonstrate the power of such action plots by a remarkable example of the wavelength‐resolved photochemistry of two triazolinedione (TAD) substrates, i.e., aliphatic and aromatic substituted, that exhibit near identical absorption spectra yet possess vastly disparate photoreactivity. We present our findings in carefully recorded action plots, from which reaction selectivity is identified. The profound difference in photoreactivity is exploited by designing a ‘hybrid’ bisfunctional TAD molecule, enabling the formation of a dual‐gated reaction manifold that demonstrates the exceptional and site‐selective (photo)chemical behavior of both TAD substrates within a single small molecule. The power of action plots is demonstrated by unveiling a reaction selective window between two different substituted triazolinediones that exhibit near identical absorbance spectra. The remarkable difference in photoreactivity is exploited by designing a dual‐gated reaction manifold, which demonstrates the site‐selective (photo)chemical behavior of both triazolinedione substrates within a single small molecule.