Synthesis of aza-BODIPY dyes bearing the naphthyl groups at 1,7-positions and application for singlet oxygen generation

Abstract

Using 2-vinylnaphthalene, aza-BODIPYs with the naphthyl groups at 1,7-positions were prepared and their photophysical properties were characterized. Due to attachment of the naphthyl groups at 1,7-positions, aza-BODIPYs show long-wavelength absorption and emission in the near-infrared region. The singlet oxygen generation of the dibromo substituted aza-BODIPY with the naphthyl groups at 1,7-positions as a photosensitizer was more effective than that of the corresponding aza-BODIPY with the phenyl groups at 1,7-positions. No photobleaching of the naphthyl-containing aza-BODIPY was observed and such NIR aza-BODIPY could be used for the singlet oxygen generation.