Aie-active photosensitizer for selective bacterial elimination and cancer cell ablation
A technology for cancer cells and photosensitizers, applied in the field of photosensitizers, can solve the problems of high cost, complicated synthesis and difficulty
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Embodiment 1
[0084] Synthesis of Compound 1
[0085] Pd(PPh 3 ) 2 Cl 2 (0.078mmol, 58mg), CuI (0.13mmol, 24.8mg) and 4-bromotriphenylamine (1.3mmol, 421.5mg), and purged the flask with argon. Anhydrous toluene (8 mL) and DBU (7.8 mmol, 1.17 mL) were added sequentially via syringe under argon sparging. Ice-cold trimethylsilylacetylene (0.65 mmol, 92 uL) was then added via syringe, followed immediately by distilled water (0.52 mmol, 9.36 uL). The reaction flask was covered with aluminum foil and stirred at high rate for 20 h at 80 °C. The reaction mixture was then extracted in DCM and distilled water. The organic layer was washed with 10% HCl and brine, and washed with MgSO 4 dry. The crude product was purified by silica gel column chromatography with hexane / ethyl acetate (5:1, v / v) with a yield of 65%. 1 H NMR (400MHz, CD 2 Cl 2 ), δ (ppm): 7.39–7.31 (m, 4H), 7.34–7.23 (m, 8H), 7.18–7.02 (m, 12H), 7.03–6.94 (m, 4H). 13 C NMR (100MHz, CD 2 Cl 2 ), δ (ppm): 147.08, 146.58, 131....
Embodiment 2
[0087] Synthesis of 4TPA-BQ
[0088] Add 2-methylallylamine (0.15mmol, 14.03mg), 4,4'-((1,2-ethynediyl)bis[N,N-diphenylaniline] (0.45 mmol, 229mg), copper acetate (0.75mmol, 149.7mg), [Cp*RhCl 2 ] 2 (0.0075mmol, 4.63mg), sodium tetrafluoroborate (0.225mmol, 24.7mg) and methanol. The resulting solution was stirred overnight at 130 °C and washed with anhydrous MgSO 4 dry. The crude product was purified by silica gel column chromatography with DCM:MeOH (25:1, v:v) in 81% yield. 1 H NMR (400MHz, CD 2 Cl 2 ),δ(ppm):8.60(s,1H),7.97(s,1H),7.90(d,J=9.6Hz,1H),7.42–7.27(m,21H),7.21–7.03(m,24H) ,6.98–6.96(m,5H),6.89–6.84(m,4H),2.50(s,3H). 13 C NMR (100MHz, CD 2 Cl 2 ),δ(ppm):152.03,150.03,149.72,148.12,147.91,147.56,147.30,145.33,143.39,142.17,139.33,139.06,137.01,136.34,133.37,133.08,132.35,131.79,131.28,131.19,130.50,130.34 ,130.23,130.10,129.95,128.37,127.24,126.88,126.15,125.82,125.13,124.98,124.60,123.96,123.57,123.12,122.10,120.31,118.24,112.78,18.94.HRMS(MALDI-TOF):m / ...
Embodiment 3
[0092] Photophysical properties of 4TPA-BQ
[0093] 4TPA-BQ was well characterized by NMR, high resolution mass spectrometry and single crystal X-ray diffraction analysis (Table 1). The obtained data were in good agreement with the proposed structure (Fig. 1 to image 3 , Figure 5 ).
[0094] Table 1. Photophysical properties of 4TPA-BQ
[0095]
[0096] Will a τ is defined by the formula τ=ΣA i (τ i ) 2 / ΣA i τ i Calculated mean fluorescence lifetime,
[0097] where A i is the pre-exponential factor τ of lifetime i . b k r = Φ / τ. c k nr =1 / τ-k r .
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