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Materials 2020, 13, 2646 6 of 24 (0.64 mL, 1.28 mmol) was added. After 24 h of stirring at room temperature, the reaction mixture was placed into a separating funnel, and washed twice with cold distilled water. After being separated by decantation, the organic layer was dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting product was dissolved in methanol (10 mL), and an equal volume of a 14% (w/v) aqueous potassium iodide solution was added. After 2 h of stirring at room temperature, the precipitated dye was collected by filtration under reduced pressure, washed with cold distilled water, and recrystallized from dichloromethane/methanol/diethyl ether. Dark green crystals. Yield 70%. M.p. 277–279 ◦C (dec). Vis-NIR λmax (ACN): 658 nm, log ε = 5.83; Vis-NIR λmax (ACT): 664 nm, log ε = 5.85; Vis-NIR λmax (DCM): 669 nm, log ε = 5.84; Vis-NIR λmax (DMF): 674 nm, log ε = 5.79; Vis-NIR λmax (DMSO): 679 nm, log ε = 5.80; Vis-NIR λmax (DXN): 680 nm, log ε = 5.74; Vis-NIR λmax (EtOH): 667 nm, log ε = 5.84; Vis-NIR λmax (MeOH): 684 nm, log ε = 5.81; Vis-NIR λmax (THF): 680 nm, log ε = 5.79; Vis-NIR λmax (XLN): 714 nm, log ε = 5.80; Vis-NIR λmax (DMEM): 625 nm, log ε = 5.10; Vis-NIR λmax (H2O): 608 nm, log ε = 5.32; Vis-NIR λmax (PBS): 628 nm; log ε = 5.09. IR νmax (KBr): 3209 (w, NH), 3102 (w, ArCH), 2929 (w, CH), 1623 (w, C=O), 1565 (w, ArC=C), 1518 (w, ArC=C), 1456 (s), 1354 (m), 1274 (s), 1251 (s), 1158 (s), 1087 (w), 1069 (w), 980 (w) cm−1. 1H NMR (600 MHz, DMSO-d6) δ: 8.95 (1H, d, J = 9.6, ArH), 8.81 (1H, s, NH), 8.70 (1H, s, NH), 8.04 (1H, d, J = 9.6, ArH), 7.94 (1H, d, J = 7.8, ArH), 7.85–7.81 (2H, m, ArH), 7.77 (1H, t, J = 7.8, ArH), 7.50–7.47 (2H, m, ArH), 7.44 (1H, t, J = 7.5, ArH), 7.22 (1H, t, J = 7.5, ArH), 6.18 (1H, s, C=CH), 5.95 (1H, s, C=CH), 4.37 (2H, br s, NCH2(CH2)4CH3), 4.16 (2H, t, J = 7.2, NCH2(CH2)4CH3), 1.77–1.67 (4H, m, NCH2CH2(CH2)3CH3 + NCH2CH2(CH2)3CH3), 1.54 (2H, qt, N(CH2)2CH2(CH2)2CH3), 1.43 (2H, qt, N(CH2)2CH2(CH2)2CH3), 1.39–1.28 (8H, m, N(CH2)3(CH2)2CH3), 0.91 (3H, t, J = 7.3, N(CH2)5CH3), 0.88 (3H, t, J = 6.9, N(CH2)5CH3) ppm. 13C NMR (150.90 MHz, DMSO-d6) δ: 175.06, 167.63, 162.43, 158.25, 154.81, 151.21, 142.32, 138.66, 136.10 (ArCH), 132.63 (ArCH), 129.16 (ArCH), 127.89, 127.44 (ArCH), 125.85 (ArCH), 125.38 (ArCH), 124.97, 124.25 (ArCH), 124.13 (ArCH), 116.30 (ArCH), 114.14 (ArCH), 93.89 (C=CH), 89.15 (C=CH), 48.13 (NCH2(CH2)4CH3), 46.53 (NCH2(CH2)4CH3), 31.05 (CH2), 30.97 (CH2), 26.93 (CH2), 26.88 (CH2), 25.77 (CH2), 25.61 (CH2), 22.16 (CH2), 22.07 (CH2), 13.89 (CH3), 13.85 (CH3) ppm. HRESI-TOFMS m/z: 586.23254 [M-I]+ (C34H40N3OSe+, calc. 586.23334). 2.1.6. Synthesis of 1-Hexyl-2-[3-(3-hexylbenzoselenazol-2(3H)-ylidenemethyl)-2-methylamino- 4-oxocyclobut-2-enylidenemethyl]-quinolin-1-ium Iodide (12) To a solution of squaraine dye 10 (0.20 g, 0.27 mmol) in anhydrous dichloromethane (20 mL), under nitrogen atmosphere at room temperature, an excess of 2 M methylamine solution in tetrahydrofuran (0.64 mL, 1.28 mmol) was added. After 1 h of stirring at room temperature, the reaction mixture was placed into a separating funnel and washed twice with cold distilled water. The organic layer after separated by decantation was dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting product was dissolved in methanol (10 mL), and an equal volume of a 14% (w/v) aqueous potassium iodide solution was added. After 2 h of stirring at room temperature, the precipitated dye was collected by filtration under reduced pressure, washed twice with cold distilled water, and recrystallized from dichloromethane/diethyl ether. Dark-purple crystals. Yield 67%. M.p. 212–214 ◦C. Vis-NIR λmax (ACN): 671 nm, log ε = 5.76; Vis-NIR λmax (ACT): 676 nm, log ε = 5.81; Vis-NIR λmax (DCM): 681 nm, log ε = 5.71; Vis-NIR λmax (DMF) = 686 nm, log ε = 5.70; Vis-NIR λmax (DMSO): 690 nm, log ε = 5.75; Vis-NIR λmax (DXN): 689 nm, log ε = 5.69; Vis-NIR λmax (EtOH): 677 nm, log ε = 5.77; Vis-NIR λmax (MeOH): 695 nm, log ε = 5.76; Vis-NIR λmax (THF): 689 nm, log ε = 5.74; Vis-NIR λmax (XLN): 718 nm, log ε = 5.72; Vis-NIR λmax (DMEM): 638 nm, log ε = 5.01; Vis-NIR λmax (H2O): 617 nm, log ε = 5.27; Vis-NIR λmax (PBS): 778 nm; log ε = 5.20. IR νmax (KBr): 3234 (w, NH), 3065 (w, ArCH), 2929 (w, CH), 1624 (m, C=O), 1565 (m, ArC=C), 1454 (s), 1432 (s), 1344 (s), 1255 (s), 1159 (s), 1112 (s), 1055 (w), 1028 (m), 988 (m), 747 (w), 637 (w) cm−1. 1H NMR (600 MHz, DMSO-d6) δ: 8.97 (1H, d, J = 9.0, ArH), 8.91–8.88 (2H, m, ArH + NH), 8.80 (1H, br q, NH), 8.09 (1H, d, J = 9.6, ArH), 7.97–7.94 (2H, m, ArH), 7.90 (1H, d, J = 7.2, ArH), 7.88–7.82 (3H, m, ArH), 7.78 (2H, br t, J = 7.5, Ar-H), 7.72 (1H, t, J = 7.5, ArH), 7.52–7.40 (6H, m, ArH), 7.24 (1H, t, J = 7.5, ArH), 7.19 (1H, t, J = 7.5, ArH) 6.15 (1H, s, C=CH),PDF Image | Photophysicochemical Light Antiproliferative vs cancer
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