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Zinc(II) tetrakis({2-Deoxy-3,5-bis[O-(p-toluoyl)]-α,β-d-ribofuranosyl}ethynyl) phthalocyaninate (4): A mixture of 2
[17]
(250.0 mg, 0.231 mmol), 3
[16]
(524.8 mg, 1.39 mmol), Pd(PPh3)2Cl2 (20 mg) and CuI (10 mg) were dried under vacuum for 1 h. To this mixture, anhyd DMF
(2.5 mL) was added followed by Et3N (1 mL) and allowed to stir at r.t. for 72 h. The solvent was removed by evaporation
and the crude green solid was purified by silica gel chromatography (EtOAc-hexane,
40:60) to furnish 4 as a blue solid (360.0 mg, 75%); IR (KBr): 2954, 2229, 1720, 1611, 1488, 1386, 1271,
1178, 1100, 1020, 837, 752 cm-1; 1H NMR (600MHz, acetone-d
6
): δ = 8.64 (br s, 8 H, Ar-H), 8.23-8.06 (m, 20 H, Ar-H), 7.42-7.37 (m, 16 H, Ar-H),
5.87-5.56 (m, 8 H, 1′,3′-H), 4.95-4.71 (m, 12 H, 4′,5′-H), 3.11-2.98 (m, 8 H, 2′-H),
2.46-2.20 (m, 24 H, Ar-CH3); MALDI-TOF MS (Matrix: dithranol): m/z calcd for: 2080.61, 2081.61, 2082.61, 2083.60, 2084.61, 2085.60; found: 2080.55,
2081.54, 2083.54, 2084.54, 2085.54; UV/Vis (dioxane): λmax (log ε) = 686 (5.5), 655 (4.6), 617 (4.7), 360 nm (5.0); UV/Vis (toluene): λmax (log ε) = 691 (5.4), 660 (4.7), 622 (4.7), 360 nm (4.9); fluorescence (DMSO): λem = 701, 764 nm [excitation at 650 nm; φf = 0.25; zinc(II) tetra-tert-butylphthalocyaninate was used as reference (φf = 0.3 in DMSO)
[4]
].
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Zinc(II) tetrakis[(2-deoxy-α,β-d-ribofunosyl)ethynyl] phthalocyaninate (1): A mixture of 4 (20.1 mg, 0.0096 mmol), and K2CO3 (14.4 mg, 0.104 mmol), in MeOH-THF (2:1, 3 mL) was stirred at r.t. for 48 h. The
reaction mixture was filtered and washed with MeOH. The MeOH was evaporated off to
furnish a dark blue solid, to which was added H2O (4.0 mL, pH adjusted to 6) and filtered. The solid was washed with H2O and 30% of acetone in H2O and purified twice by Sephadex® G-25 using MeOH as an eluent. Evaporation of the solvent gave a crude blue solid.
Further purification by recrystallization with MeOH and EtOAc gave pure 1 (8.2 mg, 80%); IR (KBr): 2954, 2229, 1720, 1611, 1488, 1386, 1271, 1178, 1100, 1020,
837, 752 cm-1; 1H NMR (600MHz, CD3OD): δ = 8.54 (br s, 8 H, Ar-H), 7.91 (br s, 4 H, Ar-H), 5.31 (br s, 4 H, 1′-H), 4.52
(br s, 2 H, 4′-H), 4.43 (br s, 2 H, 4′-H), 4.21 (br s, 2 H, 3′-H), 4.02 (br s, 2 H,
3′-H), 3.83-3.77 (m, 8 H, 5′-H), 2.87 (br s, 2 H, 2′-H), 2.53-2.41 (br s, 6 H, 2′-H);
MALDI-TOF MS (Matrix: α-CHCA): m/z calcd for: 1136.27, 1137.27, 1138.27, 1139.27, 1140.26, 1141.27, 1142.27, 1143.27;
found: 1136.27, 1137.28, 1138.29, 1139.30, 1142.23, 1143.29; UV/Vis (DMSO): λmax (log ε) = 691 (5.4), 658 (4.5), 621 (4.6), 366 nm (4.9); UV/Vis (DMSO-H2O, 1:1): λmax (log ε) = 693 (4.6), 642 (4.7), 360 nm (4.9); (DMSO-H2O, 1:19): λmax (log ε) = 689 (4.7), 638 (4.68) 348 nm (4.8); fluorescence (DMSO): λem = 701, 765 nm (φf = 0.22); (DMSO-H2O, 1:19): λem = 685, 701 nm (0.5 × 10-5 M).
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