Naphthalimide-BODIPY dyads: Synthesis, characterization, photophysical properties, live cell imaging and antimicrobial effect

NI-BODIPY-GO Nanocomposites for Targeted PDT

“…Compounds 11 and 12 and related nanocarriers ( GO - 11 and -12 ) showed a maximum absorption peak between 654 and 669 nm with a vibrational peak around 600 nm. Distyryl BODIPY derivatives 10 – 12 in dichloromethane displayed a maximum absorption peak at ∼660 nm responsive to the lowest-energy spin-allowed S 0 –S 1 transitions . Furthermore, there was a second characteristic peak around 370–380 nm due to the S 0 –S 2 transition (Figure A).…”

“…Distyryl BODIPY derivatives 10−12 in dichloromethane displayed a maximum absorption peak at ∼660 nm responsive to the lowest-energy spin-allowed S 0 −S 1 transitions. 45 Furthermore, there was a second characteristic peak around 370−380 nm due to the S 0 −S 2 transition (Figure 4A). Molar absorption coefficients (ε) of the BODIPYs (10− 12) were calculated by plotting maximum absorbance against concentration in dichloromethane (12.02, 9.03, and 7.66 × 10, 4 respectively) (Table 1 and Figures S43−S45).…”

“…The synthesis of the three new glucose-substituted NI-BODIPY dyads ( 10 – 12 ) are presented in Scheme . First, we prepared a NI-BODIPY core according to our previous report . Dibromo- and diiodo-NI-BODIPY derivatives ( 6 and 7 ) were introduced by the reaction with N -bromosuccinimide (NBS) in DCM and I 2 /HIO 3 in ethanol, respectively, to synthesize 11 and 12 .…”

“…First, we prepared a NI-BODIPY core according to our previous report. 45 Dibromo-and diiodo-NI-BODIPY derivatives (6 and 7) were introduced by the reaction with N-bromosuccinimide (NBS) in DCM and I 2 /HIO 3 in ethanol, respectively, to synthesize 11 and 12. BODIPY cores 4−6 were functionalized with aldehyde groups via double Knoevenagel condensation for the alkyne introduction and to initiate light absorption in the photodynamic window.…”

“…Synthesis compounds 1−4 were carried out according to the literature. 45,53 Synthesis of Compound 5. In a 50 mL round-bottom flask, compound 4 (0.15 g; 0.25 mmol) was dissolved in 30 mL of dichloromethane.…”