In the past decades, tetrazine-based fluorogenic labels have been widely implemented in the studies of living systems <i>via</i> bioorthogonal reactions owing to their high-performance selectivity, fast reaction kinetics, and unique fluorescent properties. Yet, the fluorescence quenching mechanism in several precursors remains elusive, which impedes the rational design to further improve their fluorescence turn-on ratios after bioorthogonal reactions. In this work, with the aid of quantum chemical calculations, we named an unique quenching mechanism – internal conversion to a dark state (ICDS), to demonstrate the fluorogenicity of tetrazine-fused fluorogenic labels with integrated <i>π</i>-conjugation systems. The factors affecting ICDS efficiency were also discussed in detail. Furthermore, we proposed various molecular design strategies to enhance fluorescence turn-on ratios in wavelength-redshifted tetrazine-functionalized labels.

Quenching mechanism of tetrazine-integrated fluorogenic labels: Internal conversion to a dark state

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