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

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 at1,7-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 at1,7-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.

Development of aryl-containing dipyrrolyldiketone difluoroboron complexes(BONEPYs):Tune the hydrogen bond o-C—H…F for fluoride recognition

Dipyrrolyldiketone difluoroboron complexes(BONEPYs)were synthesized by condensation of the corresponding pyrroles and malonyl chloride followed by treatment with BF3·OEt2.The aryl-substituted pyrrole is introduced to form a cyclic system in order to investigate anion binding studies.In BONEPYs 1-3 the o-H of the aryl group forms hydrogen bonding with F to give a more table complex.In contrast,the intramolecular hydrogen-bonded BONEPY endo-4 is more stable than its exo isomer.While adding F,the hydrogen bonds must be broken first to give 4·(3)F.Owing to the electron-rich group(-OMe),the o-H of the phenyl group can hardly interact with F via hydrogen bonding to give the less stable complex4-(5)F.The energy diffe rences between the different conformations were calculated using DFT methods,which is consistent to the experimental observations.