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Materials 2020, 13, 2646 5 of 24 Vis-NIR λmax (DMF): 689 nm, log ε = 5.04; Vis-NIR λmax (DMSO): 700 nm, log ε = 5.20; Vis-NIR λmax (DXN): 700 nm, log ε = 5.15; Vis-NIR λmax (EtOH): 674 nm, log ε = 5.18; Vis-NIR λmax (MeOH): 690 nm, log ε = 5.28; Vis-NIR λmax (THF): 706 nm, log ε = 5.11; Vis-NIR λmax (XLN): 733 nm, log ε = 5.27; Vis-NIR λmax (DMEM): 649 nm, log ε = 4.54; Vis-NIR λmax (H2O): 631 nm, log ε = 4.58; Vis-NIR λmax (PBS): 650 nm; log ε = 4.46. IR (KBr) νmax: 3059 (w, ArCH), 2926 (w, CH), 1618 (m, C=O), 1588 (s, ArC=C), 1449 (s, ArC=C), 1426 (s), 1336 (s), 1289 (s), 1239 (s), 1165 (s), 1080 (s), 974 (m), 813 (w), 746 (m) cm−1. 1H NMR (600 MHz, CDCl3) δ: 9.28 (1H, d, J = 9.6, ArH), 7.55–7.49 (4H, m, ArH), 7.37 (1H, d, J = 9.0, ArH), 7.32 (1H, t, J = 7.8, ArH), 7.27 (1H, d, J = 8.4, ArH), 7.10 (1H, t, J = 7.2, ArH), 7.03 (1H, d, J = 8.4, ArH), 6.00 (1H, s, C=CH), 5.77 (1H, s, C=CH), 4.18 (2H, t, J = 7.8, NCH2(CH2)4CH3), 4.01 (2H, t, J = 7.2, NCH2(CH2)4CH3), 1.86 (2H, br s, NCH2CH2(CH2)2CH3), 1.78 (2H, qt, NCH2CH2(CH2)2CH3), 1.54 (2H, qt, N(CH2)2CH2(CH2)2CH3), 1.48–1.32 (10H, m, N(CH2)3(CH2)2CH3 + N(CH2)2(CH2)3CH3), 0.95–0.90 (6H, m, N(CH2)5CH3) ppm. 13C NMR (150.90 MHz, CDCl3) δ: 181.01, 176.91, 173.11, 159.77, 150.98, 142.72, 139.25, 133.44 (ArCH), 131.23 (ArCH), 128.79 (ArCH), 128.46, 126.79 (ArCH), 126.58 (ArCH), 125.14, 124.91 (ArCH), 124.04 (ArCH), 123.37 (ArCH), 114.49 (ArCH), 112.42 (ArCH), 92.85 (C=CH), 88.91 (C=CH), 48.21 (NCH2(CH2)4CH3), 46.65 (NCH2(CH2)4CH3), 31.41 (CH2), 31.37 (CH2), 26.91 (CH2), 26.67 (CH2), 26.50 (CH2), 22.44 (CH2), 22.58 (CH2), 22.48 (CH2), 13.94 (CH3), 13.93 (CH3) ppm. HRESI-TOFMS m/z: 586.20943 [M]+ (C34H38N2O2Se+, calc. 586.20953). 2.1.4. Synthesis of 1-Hexyl-2-[3-(3-hexylbenzoselenazol-2(3H)-ylidenemethyl)-2-methoxy- 4-oxocyclobut-2-enylidenemethyl]quinolin-1-ium trifluoromethanesulfonate (10) To a solution of squaraine dye 9 (0.72 g, 1.23 mmol) in anhydrous dichloromethane (50 mL), stirred under nitrogen atmosphere at room temperature, an excess of methyl trifluoromethanesulfonate (0.42 mL, 3.69 mmol) was added. After 4 h, the reaction mixture was placed into a separating funnel, quenched with a cold 5% (w/v) aqueous sodium bicarbonate solution and then with cold distilled water. The organic layer, after separation by decantation, was dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The crude product was recrystallized from dichloromethane/methanol/diethyl ether. Gold greenish crystals. Yield 88%. M.p. 195–198 ◦C (dec). Vis-NIR λmax (ACN): 636 nm, log ε = 5.82; Vis-NIR λmax (ACT): 640 nm, log ε = 5.91; Vis-NIR λmax (DCM): 643 nm, log ε = 5.91; Vis-NIR λmax (DMF): 647 nm, log ε = 5.75; Vis-NIR λmax (DMSO): 651 nm, log ε = 5.82; Vis-NIR λmax (DXN): 655 nm, log ε = 5.73; Vis-NIR λmax (EtOH): 641 nm, log ε = 5.86; Vis-NIR λmax (MeOH): 661 nm, log ε = 5.86; Vis-NIR λmax (THF): 646 nm, log ε = 5.85; Vis-NIR λmax (XLN): 688 nm, log ε = 5.75. IR (KBr) νmax: 3064 (w, ArCH), 2929 (w, CH), 1619 (w, C=O), 1565 (w, ArC=C), 1505 (m, ArC=C), 1446 (s), 1414 (s), 1348 (s), 1315 (m), 1257 (s), 1214 (m), 1181 (m), 1148 (s), 1111 (s), 1051 (m), 1030 (m), 978 (w), 752 (w), 637 (w) cm−1. 1H NMR (400 MHz, CDCl3) δ: 8.74 (1H, br s, ArH), 7.90 (1H, d, J = 9.2, ArH), 7.78–7.73 (2H, m, ArH), 7.67 (2H, t, J = 8.2, ArH), 7.47 (1H, t, J = 7.2, ArH), 7.46 (1H, t, J = 7.8, ArH), 7.26–7.23 (2H, m, ArH), 6.19 (1H, s, C=CH), 5.75 (1H, s, C=CH), 4.63 (3H, s, OCH3), 4.44 (2H, t, J = 7.4 NCH2(CH2)4CH3), 4.30 (2H, t, J = 7.6, NCH2(CH2)4CH3), 1.89 (2H, qt, NCH2CH2(CH2)2CH3), 1.81 (2H, qt, NCH2CH2(CH2)2CH3), 1.58 (2H, qt, N(CH2)2CH2(CH2)2CH3), 1.49–1.39 (6H, m, N(CH2)2(CH2)3CH3), 1.36–1.31 (4H, m, N(CH2)3(CH2)2CH3), 0.94 (3H, t, J = 7.0, N(CH2)5CH3), 0.88 (3H, t, J = 7.0, N(CH2)5CH3) ppm. 13C NMR (150.90 MHz, CDCl3) δ: 163.91, 159.39, 156.74, 152.13, 142.16, 138.85, 137.42 (ArCH), 133.09 (ArCH), 129.56 (ArCH), 128.38, 127.71 (ArCH), 126.12 (ArCH), 125.57, 125.09 (ArCH), 124.97 (ArCH), 124.28 (ArCH) 121.92, 119.79, 116.05 (ArCH), 114.28 (ArCH), 92.84 (C=CH), 89.13 (C=CH), 61.23 (OCH3), 49.34 (NCH2(CH2)4CH3), 47.53 (NCH2(CH2)4CH3), 31.47 (CH2), 31.33 (CH2), 27.48 (CH2), 27.42 (CH2), 26.37 (CH2), 26.26 (CH2), 22.48 (CH2), 22.42 (CH2), 15.24 (CH3), 13.93 (CH3) ppm. LRESI-TOFMS m/z: 601.23 [M+H–CF3SO3]+. 2.1.5. Synthesis of 2-[2-Amino-3-(3-hexylbenzoselenazol-2(3H)-ylidenemethyl)-4-oxocyclobut-2- enylidenemethyl]-1-hexylquinolin-1-ium Iodide (11) 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 ammonia solution in methanolPDF Image | Photophysicochemical Light Antiproliferative vs cancer
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