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A coumarin/phenanthridine-fused heterocycle was synthesized via base-mediated annulation of N-alkylquinolinium salt and coumarin. Its potential to function as a lockable molecular switch by use of pH and redox chemistry as external stimuli was evaluated. When treated with an acid, the light yellow, fluorescent ring-closed heterocycle is instantly switched to the red, non-fluorescent ring-opened iminium salt, and this process is reverted by adding a base. The acidichromism can be selectively "locked" by converting the ring-closed and -opened compounds to their “pH-inert” forms via NBS oxidation and NaBH4 reduction, respectively. A lockable colorimetric fluorescence molecular switch is introduced.

Synthesis of a coumarin/phenanthridine-fused heterocycle as a lockable colorimetric fluorescence molecular switch