Synthesis of Naphthalimide Azocarboxylates Showing Turn‐On Fluorescence by Substitution Reaction with Sulfinates

The addition reaction of sulfinates to naphthalimide-substituted azocarboxylate afforded the sulfonyl hydrazides with high quantum yields (up to 0.91 in THF and 0.54 in methanol), which exhibited a large Stokes shift (105 nm), while the unsubstituted hydrazide and the sulfonyl-position isomer showed no fluorescence in polar solvents.

Abstract

The synthesis and characterization of sulfinate addition-responsive fluorescent molecules are described. We found that addition reaction of sulfinates to naphthalimide-substituted azocarboxylates afforded the corresponding sulfonyl hydrazides with high fluorescence quantum yields (up to 0.91 in THF and 0.54 in methanol), which exhibited a large Stokes shift (105 nm) in protic methanol solvent, while the unsubstituted hydrazide and the sulfonyl-position isomer showed no fluorescence in polar solvents.

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