Synthesis of Water-Soluble Fullerene Derivatives

Fullerene derivatives C_s-C₆₀Ar₆, C₆₀Ar₅X (X=Cl, H) and C_s-C₆₀Ar₄ (compounds 1, 3–10) were synthesized using reported approach based on the arylation of the chlorofullerene C₆₀Cl₆ with the esters of aromatic acids followed by acidic hydrolysis of ester groups (Figure 1).24 Preparative chromatography was used to separate untypical products C_s-C₆₀Ar₆ and C_s-C₆₀Ar₄. Compound 2 with the structure C₆₀Ar₅Et was obtained by treatment of the fullerene derivative 1 with P(OEt)₃ at 100°C as reported previously.25 Compounds 3, 4 and 8 were synthesized and fully characterized earlier.26 Compounds 1, 2, 5, 6, 7, 9, 10 were obtained here for the first time (see Figures S1–S37 for NMR and ESI MS data).

Synthesis of the fullerene derivatives used in this work. Conditions: i – FeCl₃, PhNO₂, 100^oC, 1h; ii – P(OEt)₃, PhCH₃, 100^oC, 1h; iii – HCl, CH₃COOH, PhCH₃, 70^oC, 3d.

Compound 1-OMe. (79%)¹H NMR (500 MHz, CDCl₃, δ, ppm): 3.71 (s, 3H), 3.74 (s, 6H), 3.76 (s, 6H), 3.78 (s, 2H), 3.83 (s, 4H), 3.87 (s, 4H), 6.81 (d, 1H, J = 3.6 Hz), 6.85–6.87 (m, 3H), 6.91 (d, 2H, J = 3.5 Hz), 7.10 (d, 2H, J = 3.5 Hz), 7.41 (d, 2H, J = 3.6 Hz).¹³C NMR (125 MHz, CDCl₃, δ, ppm): 35.38 (CH₂), 35.49 (CH₂), 35.62 (CH₂), 52.29 (CH₃), 52.32 (CH₃), 52.34 (CH₃), 54.03 (C_{sp3 fullerene cage}), 56.19 (C_{sp3 fullerene cage}), 59.60 (C_{sp3 fullerene cage}), 75.30 (C_{sp3 fullerene cage}-Cl), 126.48, 126.92, 126.95, 127.58, 129.79, 135.68, 135.93, 136.24, 140.52, 141.56, 142.14, 142.59, 142.83, 143.17, 143.46, 144.07, 144.29, 144.34, 144.59, 144.69, 144.97, 145.78, 146.66, 147.17, 147.33, 147.85, 148.21, 148.32, 148.37, 148.69, 148.76, 149.67, 150.40, 153.19, 155.55, 170.60 (COOCH₃), 170.64 (COOCH₃), 170.71 (COOCH₃). FTIR (KBr pellet, ν, cm⁻¹): 538 (M), 754 (M), 778 (M), 798 (M), 1000 (M), 1038 (M), 1166 (S), 1212 (S), 1262 (M), 1288 (M), 1310 (M), 1348 (M), 1404 (M), 1432 (M), 1460 (M), 1542 (M), 1560 (M), 1654 (M), 1736 (VS), 2336 (M), 2586 (M), 2850 (M), 2922 (M), 3396 (M), 3406 (M), 3448 (M), 3506 (W).

Compound 1-OH. (97%)¹H NMR (500 MHz, (CD₃)₂SO, δ, ppm): 3.75 (s, 2H), 3.83 (s, 4H), 3.86 (s, 4H), 6.78 (d, 1H, J = 3.5 Hz), 6.83 (d, 1H, J = 3.6 Hz), 6.91 (d, 2H, J = 3.5 Hz), 6.95 (d, 2H, J = 3.6 Hz), 7.09 (d, 2H, J = 3.5 Hz), 7.37 (d, 2H, J = 3.5 Hz).

¹³C NMR (125 MHz, (CD₃)₂SO, δ, ppm): 35.37 (CH₂), 35.54 (CH₂), 35.62 (CH₂), 54.07 (C_{sp3 fullerene cage}), 56.28 (C_{sp3 fullerene cage}), 59.64 (C_{sp3 fullerene cage}), 75.47 (C_{sp3 fullerene cage}-Cl), 126.87, 127.04, 127.45, 127.47, 127.60, 129.88, 137.90, 138.11, 138.45, 139.14, 140.21, 142.26, 142.54, 142.82, 143.10, 143.37, 143.89, 144.29, 144.30, 144.33, 144.61, 144.66, 144.93, 145.60, 146.00, 147.12, 147.26, 147.83, 148.18, 148.23, 148.32, 148.62, 148.69, 148.72, 149.95, 150.58, 153.32, 155.70, 171.79 (COOH), 171.92 (COOH), 171.93 (COOH). FTIR (KBr pellet, ν, cm⁻¹): 540 (M), 588 (M), 618 (M), 646 (M), 692 (M), 1042 (M), 1110 (W), 1236 (M), 1274 (M), 1336 (M), 1380 (S), 1442 (M), 1580 (VS), 1640 (S), 1658(M), 3364 (S), 3386 (S), 3396 (S), 3406 (S).

Compound 2-OMe. (90%)¹H NMR (500 MHz, CDCl₃, δ, ppm): 1.22 (t, 3H, J = 7.1 Hz), 2.10 (q, 2H, J = 7.1 Hz), 3.72 (s, 3H), 3.75 (s, 6H), 3.75 (s, 6H), 3.77 (s, 2H), 3.85 (s, 8H), 6.82 (d, 1H, J = 3.6 Hz), 6.87– 6.89 (m, 4H), 6.91 (d, 1H, J = 3.6 Hz), 7.11 (d, 2H, J = 3.3 Hz), 7.22 (d, 2H, J = 3.6 Hz).

¹³C NMR (125 MHz, CDCl₃, δ, ppm): 9.62 (CH₂CH₃), 32.55 (CH₂CH₃), 35.27 (CH₂), 35.53 (CH₂), 35.58 (CH₂), 52.30 (CH₃), 52.31 (CH₃), 54.24 (C_{sp3 fullerene cage}), 56.51 (C_{sp3 fullerene cage}), 59.84 (C_{sp3 fullerene cage}), 65.25 (C_{sp3 fullerene cage}), 126.12, 126.61, 126.78, 126.88, 126.90, 130.33, 135.30, 135.42, 135.97, 141.96, 142.57, 142.89, 143.09, 143.36, 143.45, 143.58, 144.17, 144.20, 144.49, 144.53, 144.78, 145.02, 146.03, 146.72, 146.99, 147.19, 147.29, 147.84, 148.12, 148.17, 148.20, 148.56, 148.58, 148.76, 150.69, 152.73, 155.50, 155.76, 170.61 (COOCH₃), 170.65 (COOCH₃), 170.69 (COOCH₃). FTIR (KBr pellet, ν, cm⁻¹): 538 (M), 796 (M), 1004 (M), 1038 (M), 1108 (S), 1168 (S), 1220 (S), 1262 (M), 1434 (S), 1710 (S), 1730 (VS), 1738 (VS), 2364 (M), 2854 (M), 2924 (S), 3430 (S).

Compound 2-OH. (96%)¹H NMR (500 MHz, (CD₃)₂SO, δ, ppm): 1.20 (t, 3H, J = 6.9 Hz), 1.97– 2.06 (m, 2H), 3.76 (s, 2H), 3.84 (s, 8H), 6.82– 6.86 (m, 2H), 6.90– 6.96 (m, 4H), 7.07 (d, 2H, J = 3.4 Hz), 7.21 (d, 2H, J = 3.4 Hz).

¹³C NMR (125 MHz, (CD₃)₂SO, δ, ppm): 9.66 (CH₂CH₃), 32.56 (CH₂CH₃), 35.34 (CH₂), 35.57 (CH₂), 35.61 (CH₂), 54.31 (C_{sp3 fullerene cage}), 56.63 (C_{sp3 fullerene cage}), 59.91 (C_{sp3 fullerene cage}), 65.20 (C_{sp3 fullerene cage}), 126.21, 126.79, 127.16, 127.39, 127.52, 130.36, 137.38, 137.63, 138.35, 140.37, 141.90, 142.80, 142.90, 143.16, 143.32, 143.61, 144.11, 144.20, 144.45, 144.51, 144.78, 144.88, 144.91, 145.04, 145.42, 146.93, 147.06, 147.16, 147.23, 147.83, 148.09, 148.12, 148.51, 148.72, 151.08, 153.12, 155.58, 156.04, 171.82 (COOH), 171.93 (COOH), 171.98 (COOH). FTIR (KBr pellet, ν, cm⁻¹): 618 (S), 758 (M), 812 (M), 1046 (S), 1116 (VS), 1216 (S), 1380 (S), 1448 (S), 1594 (S), 2344 (S), 2362 (S), 2854 (S), 2924 (VS), 3206 (VS), 3268 (VS), 3310 (VS).

Compound 5-OMe. (40%)¹H NMR (600 MHz, CDCl₃, δ, ppm): 1.67 (m, 10Н), 1.98 (m, 10Н), 2.61 (t, 2Н), 2.66 (t, 4Н), 2.71 (t, 4Н), 3.38 (t, 1Н), 3.42 (t, 2Н), 3.44 (t, 2Н), 3.73 (s, 6Н), 3.75 (s, 12Н), 3.76 (s, 12Н), 5.24 (s, 1Н), 6.98 (d, 2Н), 7.01 (d, 4Н), 7.15 (d, 4Н), 7.32 (d, 2Н), 7.50 (d, 4Н), 7.67 (d, 4Н).

¹³C NMR (150 MHz, CDCl₃, δ, ppm): 28.35 (CH₂), 28.39 (CH₂), 28.42 (CH₂), 29.00 (CH₂), 29.06 (CH₂), 34.89 (CH₂), 34.95 (CH₂), 35.02 (CH₂), 51.52 (CH), 52.51 (CH₃), 52.54 (CH₃), 58.67 (C_{sp3 fullerene cage}), 58.73 (C_{sp3 fullerene cage}), 60.77 (C_{sp3 fullerene cage}), 62.91 (C_{sp3 fullerene cage}), 127.78, 128.08, 128.21, 128.63, 128.78, 128.89, 137.43, 137.47, 140.66, 140.93, 141.13, 143.12, 143.39, 143.81, 144.03, 144.11, 144.23, 144.33, 144.53, 145.47, 145.73, 145.98, 146.23, 146.91, 147.10, 147.20, 147.74, 147.94, 148.06, 148.25, 148.38, 148.67, 148.72, 151.78, 152.37, 152.61, 156.20, 169.78 (СOOCH₃).

Compound 5-OH. (96%)¹H NMR (600 MHz, (CD₃)₂CO, CS₂, δ, ppm): 1.50–1.75 (m, 10Н), 1.75–1.97 (m, 10Н), 2.57 (t, 2Н), 2.63 (t, 4Н), 2.71 (t, 4Н), 3.27–3.40 (m, 5Н), 5.36 (s, 1Н), 6.99 (d, 2Н), 7.04 (d, 4Н), 7.20 (d, 4Н), 7.25 (d, 2Н), 7.49 (d, 4Н), 7.71 (d, 4Н).

¹³C NMR (150 MHz, (CD₃)₂CO, CS₂, δ, ppm): 28.19 (CH₂), 28.28 (CH₂), 28.42 (CH₂), 29.79 (CH₂), 34.96 (CH₂), 35.03 (CH₂), 35.15 (CH₂), 51.16 (CH), 51.18 (CH), 51.21 (CH), 58.72 (C_{sp3 fullerene cage}), 58.82 (C_{sp3 fullerene cage}), 60.86 (C_{sp3 fullerene cage}), 63.14 (C_{sp3 fullerene cage}), 127.76, 128.13, 128.26, 128.85, 128.95, 129.03, 129.16, 136.80, 136.83, 141.18, 141.40, 141.58, 143.21, 144.04, 144.11, 144.18. 144.20, 144.29, 144.42, 144.78, 144.83, 145.69, 145.98, 146.19, 146.73, 146.95, 147.15, 147.25, 147.76, 148.10, 148.28, 148.31, 148.41, 148.69, 148.73, 152.08, 152.63, 152.77, 156.58, 170.49 (СOOH), 170.58 (СOOH), 170.70 (СOOH).

Compound 6-OMe. (5%)¹H NMR (500 MHz, CDCl₃, δ, ppm): 3.26 (s, 8H), 3.43 (s, 8H), 3.55 (s, 4H), 3.65 (s, 4H), 3.69 (s, 8H), 3.72 (s, 8H), 6.80 (dd, 2H, J = 8.2, 2.0 Hz), 6.98 (d, 2H, J = 1.9 Hz), 7.15 (dd, 2H, J = 8.1, 2.0 Hz), 7.17 (d, 2H, J = 1.8 Hz), 7.56 (d, 2H, J = 8.2 Hz), 7.98 (d, 2H, J = 8.0 Hz).

¹³C NMR (125 MHz, CDCl₃, δ, ppm): 40.46 (CH₂), 40.61 (CH₂), 51.90, 52.13, 52.24, 59.75 (C_{sp3 fullerene cage}), 60.15 (C_{sp3 fullerene cage}), 128.22, 128.77, 128.96, 129.15, 131.04, 131.24, 131.50, 133.07, 133.15, 133.95, 134.09, 134.76, 134.80, 136.07, 136.43, 137.40, 140.68, 142.19, 142.32, 142.77, 143.04, 143.46, 143.70, 143.93, 145.06, 145.23, 145.61, 145.68, 146.52, 146.73, 146.85, 147.35, 147.40, 147.50, 148.29, 148.41, 148.82, 149.19, 149.61, 149.78, 152.40, 162.24, 171.60 (COOCH₃), 171.67 (COOCH₃), 171.77 (COOCH₃), 171.91 (COOCH₃).

ESI MS: m/z= 1606 ([M]⁻).

Compound 6-OH. (95%)¹H NMR (600 MHz, (CD₃)₂SO, δ, ppm): 3.47 (s, 8H), 3.60 (s, 8H), 6.75 (d, 2H, J = 8.3 Hz), 6.99 (m, 2H), 7.17– 7.25 (m, 4H), 7.52 (d, 2H, J = 8.2 Hz), 8.04 (d, 2H, J = 8.0 Hz), 12.32 (s, 8H).

¹³C NMR (125 MHz, (CD₃)₂SO, δ, ppm): 40.62 (CH₂), 40.65 (CH₂), 59.42 (C_{sp3 fullerene cage}), 59.79 (C_{sp3 fullerene cage}), 128.35, 129.00, 130.40, 132.31, 133.42, 133.75, 134.55, 134.80, 134.94, 135.43, 136.60, 137.09, 137.32, 139.74, 141.82, 141.89, 142.21, 142.61, 142.81, 143.12, 143.67, 144.72, 144.99, 145.16, 145.44, 145.49, 145.81, 145.85, 146.19, 146.60, 146.81, 147.37, 147.48, 147.78, 147.99, 148.28, 148.47, 148.78, 149.19, 149.91, 152.33, 162.52, 172.36 (COOH), 172.44 (COOH), 172.46 (COOH), 172.52 (COOH).

Compound 7-OMe. (10%)¹H NMR (500 MHz, CDCl₃, δ, ppm): 3.56 (s, 5H), 3.58– 3.61 (m, 15H), 3.63 (s, 5H), 3.67– 3.71 (m, 25H), 7.08 (m, 2H), 7.18 (d, 1H, J = 7.9 Hz), 7.21 (d, 1H, J = 7.7 Hz), 7.23 (d, 1H, J = 8.6 Hz), 7.25– 7.27 (m, 1H), 7.30 (d, 1H, J = 8.0 Hz), 7.45 (d, 1H, J = 2.1 Hz), 7.49 (d, 1H, J = 2.0 Hz), 7.51 (dd, 1H, J = 7.9, J = 2.1 Hz), 7.54 (dd, 1H, J = 7.8, J = 2.0 Hz), 7.72– 7.74 (m, 3H), 7.86 (dd, 1H, J = 7.9, J = 2.0 Hz).

¹³C NMR (125 MHz, CDCl₃, δ, ppm): 38.36 (CH₂), 38.50 (CH₂), 38.76 (CH₂), 38.78 (CH₂), 38.87 (CH₂), 52.01 (CH₃), 52.08 (CH₃), 52.12 (CH₃), 52.15 (CH₃), 52.22 (CH₃), 57.84 (C_{sp3 fullerene cage}), 57.97 (C_{sp3 fullerene cage}), 60.39 (C_{sp3 fullerene cage}), 60.53 (C_{sp3 fullerene cage}), 63.13 (C_{sp3 fullerene cage}), 76.08 (C_{sp3 fullerene cage}-Cl), 127.64, 127.68, 127.85, 128.07, 128.47, 128.65, 130.46, 131.18, 131.24, 131.40, 131.60, 132.61, 132.89, 133.06, 133.17, 133.24, 133.30, 134.01, 134.18, 134.20, 134.22, 134.30, 136.98, 137.27, 138.47, 142.82, 142.85, 142.97, 142.99, 143.18, 143.35, 143.36, 143.82, 143.85, 143.86, 143.90, 144.22, 144.30, 144.40, 144.43, 144.50, 144.72, 144.56, 145.10, 145.26, 145.44, 145.51, 146.57, 146.63, 147.36, 147.39, 147.50, 147.53, 147.94, 148.03, 148.32, 148.60, 148.62, 148.72, 148.82, 148.86, 148.90, 148.93, 148.97, 150.08, 150.67, 150.98, 151.29, 153.44, 154.29, 156.16, 156.62, 171.22 (COOCH₃), 171.25 (COOCH₃), 171.27 (COOCH₃), 171.28 (COOCH₃), 171.32 (COOCH₃), 171.35 (COOCH₃), 171.41 (COOCH₃), 171.47 (COOCH₃), 171.50 (COOCH₃).

ESI MS: m/z= 1827 ([M-Cl]⁻).

Compound 7-OH. (96%)¹H NMR (500 MHz, D₂O, δ, ppm): 3.24– 3.32 (m, 4H), 3.35 (s, 4H), 3.28– 3.45 (m, 4H), 3.45– 3.51 (m, 8H), 6.61– 6.67 (m, 2H), 6.77 (dd, 1H, J = 8.0, 1.8 Hz), 6.95–7.05 (m, 2H), 7.08– 7.24 (m, 6H), 7.44 (s, 2H), 7.68 (s, 2H) (for potassium salt form).

¹³C NMR (125 MHz, (CD₃)₂SO, δ, ppm): 38.44 (CH₂), 38.53 (CH₂), 38.57 (CH₂), 38.86 (CH₂), 38.88 (CH₂), 57.79 (C_{sp3 fullerene cage}), 57.85 (C_{sp3 fullerene cage}), 60.46 (C_{sp3 fullerene cage}), 60.60 (C_{sp3 fullerene cage}), 63.12 (C_{sp3 fullerene cage}), 76.24 (C_{sp3 fullerene cage}-Cl), 126.62, 127.34, 127.49, 128.77, 130.51, 130.79, 131.05, 131.16, 131.72, 131.89, 132.03, 132.43, 132.49, 134.26, 134.36, 134.39, 134.52, 134.58, 134.85, 135.29, 135.41, 135.65, 135.69, 135.73, 135.78, 135.81, 137.86, 137.98, 138.80, 142.68, 143.02, 143.07, 143.62, 143.85, 144.14, 144.24, 145.49, 145.56, 145.89, 146.03, 147.13, 147.21, 147.23, 147.27, 147.36, 147.46, 147.73, 147.80, 147.84, 147.93, 148.05, 148.36, 148.43, 148.51, 148.61, 148.70, 151.69, 152.34, 156.21, 159.58, 172.14 (COOH), 172.38 (COOH), 172.45 (COOH), 172.52 (COOH), 172.54 (COOH), 172.77 (COOH), 172.96 (COOH) (for acid form).

Compound 9-OMe. (25%)¹H NMR (500 MHz, CDCl₃, δ, ppm): 3.67 (s, 2H), 3.70 (s, 4H), 3.73 (s, 4H), 3.74 (s, 3H), 3.76 (s, 6H), 3.78 (s, 6H), 5.21 (s, 1H), 7.25 (d, 2H, J = 8.7 Hz), 7.29 (d, 4H, J = 8.6 Hz), 7.32 (d, 2H, J = 8.6 Hz), 7.42 (d, 4H, J = 8.5 Hz), 7.53 (d, 4H, J = 8.5 Hz), 7.71 (d, 4H, J = 8.5 Hz).

¹³C NMR (125 MHz, CDCl₃, δ, ppm): 36.08 (CH₂), 36.29 (CH₂), 36.34 (CH₂), 52.65 (CH₃), 52.68 (CH₃), 52.72 (CH₃), 58.39 (C_{sp3 fullerene cage}), 58.52 (C_{sp3 fullerene cage}), 60.51 (C_{sp3 fullerene cage}), 62.89 (C_{sp3 fullerene cage}), 127.73, 128.25, 128.59, 128.71, 129.98, 130.08, 130.34, 130.56, 132.60, 134.58, 134.76, 135.04, 138.25, 138.28, 143.28, 143.53, 144.02, 144.17, 144.28, 144.36, 144.45, 145.20, 145.51, 145.70, 146.91, 147.11, 147.20, 147.38, 147.79, 148.15, 148.19, 148.31, 148.44, 148.72, 148.82, 148.86, 151.13, 151.86, 152.42, 155.73, 169.83 (COOCH₃), 169.85 (COOCH₃).

ESI MS: m/z= 1626 ([M-H]⁻).

Compound 9-OH. (95%)¹H NMR (500 MHz, (CD₃)₂SO, δ, ppm): 3.77 (s, 2H), 3.79 (s, 4H), 3.85 (s, 4H), 5.77 (s, 1H), 7.12 (d, 2H, J = 8.3 Hz), 7.17 (d, 2H, J = 8.5 Hz), 7.22 (d, 4H, J = 8.4 Hz), 7.36 (d, 4H, J = 8.3 Hz), 7.64 (d, 4H, J = 8.3 Hz), 7.85 (d, 4H, J = 8.3 Hz).

¹³C NMR (125 MHz, (CD₃)₂SO, δ, ppm): 35.18 (CH₂), 35.48 (CH₂), 35.68 (CH₂), 58.19 (C_{sp3 fullerene cage}), 58.48 (C_{sp3 fullerene cage}), 60.54 (C_{sp3 fullerene cage}), 62.62 (C_{sp3 fullerene cage}), 128.16, 128.36, 128.44, 128.69, 128.78, 128.84, 128.98, 129.39, 135.80, 136.10, 136.28, 136.44, 136.54, 142.49, 143.05, 143.57, 143.90, 143.97, 143.99, 144.13, 144.21, 144.74, 145.63, 145.85, 145.90, 146.58, 146.74, 146.95, 147.06, 147.56, 147.89, 147.93, 148.08, 148.18, 148.22, 148.50, 148.58, 151.98, 152.68, 153.36, 156.51, 170.82 (COOH), 170.88 (COOH), 170.93 (COOH).

ESI MS: m/z= 1556 ([M-H]⁻).

Compound 10-OMe. (8%)¹H NMR (500 MHz, CDCl₃, δ, ppm): 3.74 (s, 3H), 3.78 (s, 3H), 3.81 (s, 6H), 3.84 (s, 6H), 4.46 (s, 2H), 4.48 (s, 2H), 4.65 (s, 4H), 4.70 (s, 4H), 6.01 (d, 2H, J = 8.8 Hz), 6.44 (d, 2H, J = 8.9 Hz), 6.57 (d, 2H, J = 8.8 Hz), 6.79 (d, 4H, J = 8.8 Hz), 6.88 (d, 4H, J = 8.8 Hz), 7.12 (d, 2H, J = 8.8 Hz), 7.51 (d, 4H, J = 8.7 Hz), 7.65 (d, 4H, J = 8.7 Hz).

¹³C NMR (125 MHz, CDCl₃, δ, ppm): 52.14 (CH₃), 52.19 (CH₃), 52.33 (CH₃), 57.26 (C_{sp3 fullerene cage}), 60.94 (C_{sp3 fullerene cage}), 63.29 (C_{sp3 fullerene cage}), 65.01 (CH₂), 65.04 (CH₂), 65.30 (CH₂), 65.34 (CH₂), 72.30 (C_{sp3 fullerene cage}), 112.20, 113.56, 114.86, 115.36, 127.04, 127.73, 129.10, 129.61, 129.99, 130.09, 130.21, 130.56, 131.23, 131.69, 132.59, 133.09, 133.38, 135.70, 138.42, 142.41, 142.80, 143.00, 143.85, 144.01, 144.05, 144.26, 144.37, 144.60, 145.33, 145.69, 147.17, 147.30, 147.53, 147.92, 148.24, 148.34, 148.62, 148.66, 148.83, 148.86, 149.85, 154.15, 155.49, 156.02, 157.33, 157.40, 157.67, 158.94, 169.09 (COOCH₃), 169.13 (COOCH₃), 169.18 (COOCH₃).

ESI MS: m/z= 1711 ([M]⁻).

Compound 10-OH. (98%)¹H NMR (500 MHz, (CD₃)₂CO, δ, ppm): 4.41 (s, 4H), 4.61 (s, 4H), 4.67 (s, 4H), 6.05 (d, 2H, J = 8.2 Hz), 6.46 (d, 2H, J = 7.8 Hz), 6.65 (d, 2H, J = 7.7 Hz), 6.84 (d, 4H, J = 7.9 Hz), 6.94 (d, 4H, J = 7.7 Hz), 7.22 (d, 2H, J = 7.3 Hz), 7.56 (d, 4H, J = 7.7 Hz), 7.71 (d, 4H, J = 7.8 Hz).

¹³C NMR (125 MHz, (CD₃)₂CO, δ, ppm): 57.29 (C_{sp3 fullerene cage}), 61.06 (C_{sp3 fullerene cage}), 63.34 (C_{sp3 fullerene cage}), 64.50 (CH₂), 64.58 (CH₂), 64.62 (CH₂), 72.45 (C_{sp3 fullerene cage}), 112.12, 113.74, 115.01, 129.10, 129.42, 129.86, 130.15, 131.28, 131.64, 132.49, 132.71, 135.40, 137.91, 142.73, 142.91, 143.11, 143.72, 143.93, 143.98, 144.25, 144.43, 144.56, 145.39, 145.57, 146.91, 147.22, 147.54, 147.78, 148.12, 148.18, 148.28, 148.54, 148.77, 148.87, 150.15, 154.15, 154.44, 155.75, 156.31, 157.65, 157.73, 157.79, 159.33, 170.03 (COOH), 170.12 (COOH), 170.40 (COOH).

ESI MS: m/z= 1626 ([M-H]⁻), 812 ([M-2H]^2-).