Systemic study on fluorescent switching systems composed of naphthopyran and benzimidazole in solution and film forms

• A system of fluorescent photoswitchings based on benzimidazole-naphthopyran dyads was designed and prepared.
• The fluorescence emission of benzimidazole can be efficiently modulated by photochromism of naphthopyran.
• Photoinduced energy transfer is responsible for the modulation of fluorescence emission.
• The non-destructive readout ability of synthesized dyads in doped PMMA film was achieved.

The fluorescent photo-switching systems were prepared based on fluorescent benzimidazole and photochromic naphthopyran. Naphthopyran in this systems displayed excellent photochromic performance in tetrahydrofuran solutions and in PMMA films. The fluorescent emission of benzimidazole was modulated between “on” and “off” via the photoisomerization of naphthopyran in high-contrast due to the photoinduced energy transfer from benzimidazole to the open-form naphthopyran. Both the fluorescent photoswitching and the photochromism of benzimidazole-naphthopyran dyads in solutions and films displayed excellent fatigue resistance. The spaces between benzimidazole and naphthopyran affect the absorbance and fluorescence spectra of benzimidazole-naphthopyran dyads. The non-destructive readout ability of synthesized dyads in doped PMMA film was achieved.

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