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Synlett 2009(12): 2028-2034  
DOI: 10.1055/s-0029-1217528
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Self-Folded Molecular Rotors Controlled by Edge-to-Face CH/π Aromatic Interactions

Yitao Li, Yanping Zhu, Jing Qin, Huizhen Guo, Lin Li, Anxin Wu*
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079,P. R. of China
e-Mail: chwuax@mail.ccnu.edu.cn;
Further Information

Publication History

Received 25 March 2009
Publication Date:
01 July 2009 (online)

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Abstract

A series of novel self-folded molecular rotors were synthesized and characterized by ¹H NMR, ¹³C NMR, HRMS, and IR data. All but two compounds were also studied by X-ray crystallography.

Key words

self-folded - molecular rotors - CH/p interactions - ­molecular clips - diethoxycarbonyl glycoluril

    References and Notes

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9

Special Issue of Scientific American: Nanotech: The Science of Small Gets Down to Business, September 2001.

17

Synthesis of 7; General Procedure
DMF and the aliphatic amines had to be freshly distilled or recrystallized under nitrogen. Compounds 4 and 5a-g were synthesized as reported previously.¹5 The intermediates 5h and 5i were then produced from 5g through Sonogashira cross-coupling reactions. Thus, a suspension of 5 (5 mmol) in 37% aq formaldehyde (3.5 mL) and DMF (30 mL) was brought to reflux under magnetic stirring. A solution of aliphatic amine (5 mmol) in DMF (20 mL) was added slowly, dropwise (over 1 h) to the mixture. Refluxing was continued and the reaction was monitored by TLC. Upon completion, the solvent was removed under reduced pressure and the products were separated by column chromatography on silica gel (CHCl3-MeOH) to give compound 7 as a solid.

18

Compound 7a: Yield: 58%; white solid; mp 159-160 ˚C; IR (KBr): 2960, 2923, 2852, 1737, 1635, 1377, 1267, 752, 722 cm-¹; ¹H NMR (CDCl3, 400 MHz): δ = 7.50-7.47 (m, 2 H), 7.30-7.19 (m, 5 H), 6.88-6.85 (m, 2 H), 4.86 (d, J = 15.6 Hz, 2 H), 4.65 (d, J = 15.2 Hz, 4 H), 4.39-4.25 (m, 6 H), 2.88 (s, 2 H), 1.38-1.25 (m, 6 H); ¹³C NMR (CDCl3,100 MHz): δ = 165.9, 165.6, 156.9, 136.2, 130.0, 129.0, 128.0, 127.4, 114.2, 80.3, 75.9, 63.3, 63.2, 59.8, 53.7, 45.5, 14.0, 13.9; HRMS: m/z [M + H]+ calcd for C27H29N5O6: 519.2118; found: 520.2191.
Compound 7b: Yield: 45%; white solid; mp 160-161 ˚C; IR (KBr): 3064, 2973, 2938, 1738, 1718, 1452, 1414, 1263, 752 cm-¹; ¹H NMR (CDCl3, 400 MHz): δ = 7.24-7.18 (m, 5 H), 6.85-6.82 (m, 2 H), 4.77 (d, J = 15.6 Hz, 2 H), 4.62 (d, J = 13.6 Hz, 2 H), 4.57 (d, J = 15.6 Hz, 2 H), 4.37-4.24 (m, 6 H), 2.87 (s, 2 H), 2.22 (s, 6 H), 1.36-1.28 (m, 6 H); ¹³C NMR (CDCl3, 100 MHz): δ = 165.9, 165.7, 156.9, 136.5, 136.0, 133.4, 131.2, 128.9, 127.9, 127.2, 80.4, 75.9, 63.1, 63.0, 59.8, 53.7, 45.0, 19.1, 13.9, 13.8; HRMS: m/z [M + H]+ calcd for C29H33N5O6: 547.2431; found: 548.2504.
Compound 7c: Yield: 67%; white solid; mp 228-229 ˚C; IR (KBr): 3069, 2957, 2936, 2852, 1762, 1718, 1465, 1417, 1282, 741 cm-¹; ¹H NMR (CDCl3, 400 MHz): δ = 7.21-7.19 (m, 3 H), 7.00-6.91 (m, 4 H), 4.78 (d, J = 16.0 Hz, 2 H), 4.68 (d, J = 14.0 Hz, 2 H), 4.61 (d, J = 16.0 Hz, 2 H), 4.40-4.28 (m, 6 H), 3.91 (s, 6 H), 2.94 (s, 2 H), 1.38-1.30 (m, 6 H); ¹³C NMR (CDCl3, 100 MHz): δ = 165.9, 165.7, 156.9, 147.7, 136.3, 128.9, 128.7, 127.9, 127.2, 113.3, 80.3, 76.0, 63.2, 63.1, 59.8, 56.0, 53.6, 45.1, 13.9, 13.8; HRMS: m/z
[M + H]+ calcd for C29H33N5O8: 579.2329; found: 580.2402.
Compound 7d: Yield: 45%; yellow solid; mp 247-248 ˚C; IR (KBr): 3061, 2927, 2852, 1761, 1743, 1721, 1457, 1420, 1251, 752 cm-¹; ¹H NMR (CDCl3, 400 MHz): δ = 7.42-7.21 (m, 5 H), 6.95 (d, J = 6.8 Hz, 2 H), 5.67 (d, J = 16.0 Hz, 2 H), 4.68 (d, J = 13.6 Hz, 2 H), 4.57 (d, J = 16.0 Hz, 2 H), 4.40-4.26 (m, 6 H), 3.00 (s, 2 H), 1.38-1.30 (m, 6 H); ¹³C NMR (CDCl3, 100 MHz): δ = 165.7, 165.5, 156.7, 137.8, 136.2, 133.9, 129.1, 128.1, 127.4, 124.2, 79.0, 76.4, 63.4, 63.2, 59.9, 54.0, 44.9, 14.0, 13.9; HRMS: m/z [M + H]+ calcd for C27H27Br2N5O6: 675.0328; found: 676.0401. Compound 7e: Yield: 50%; white solid; mp 163-165 ˚C; IR (KBr): 3448, 2984, 1772, 1619, 1533, 1459, 1420, 1368, 1319, 1259, 1224, 1154, 1099, 1077, 1027, 980, 914, 852, 815
cm-¹; ¹H NMR (CDCl3, 400 MHz): δ = 7.44 (s, 1 H), 7.29-7.23 (m, 3 H), 6.93-6.92 (d, J = 6.8 Hz, 2 H), 4.93 (d, J = 16.0 Hz, 1 H), 4.87 (d, J = 16.0 Hz, 1 H), 4.85-4.53 (m, 4 H), 4.37-4.25 (m, 6 H), 2.90 (s, 2 H), 2.33 (s, 3 H), 2.20 (s, 3 H), 1.37-1.29 (m, 6 H); ¹³C NMR (CDCl3, 150 MHz): δ = 165.6, 165.4, 156.9, 156.4, 152.1, 138.5, 136.3, 135.0, 133.2, 129.1, 128.1, 127.4, 126.3, 79.7, 76.0, 63.4, 63.2, 59.9, 59.8, 53.9, 45.2, 39.7, 19.9, 14.5, 13.9, 13.8; HRMS: m/z [M + H]+ calcd for C29H32N6O8: 592.2282; found: 593.2354.
Compound 7f: Yield: 52%; white solid; mp 158-160 ˚C; IR (KBr): 3062, 2977, 2937, 2847, 1754, 1718, 1520, 1470, 1423, 1276, 814, 744 cm-¹; ¹H NMR (CDCl3, 400 MHz):
δ = 7.86 (d, J = 9.2 Hz, 1 H), 7.28-7.22 (m, 3 H), 6.93-6.89 (m, 3 H), 5.80 (d, J = 16.8 Hz, 1 H), 5.74 (d, J = 16.0 Hz, 1 H), 4.68 (d, J = 14.0 Hz, 1 H), 4.62 (d, J = 16.8 Hz, 1 H), 4.52 (d, J = 14.4 Hz, 1 H), 4.40 (d, J = 14.0 Hz, 1 H), 4.38-4.21 (m, 6 H), 4.00 (s, 3 H), 2.99 (d, J = 13.2 Hz, 1 H), 2.66 (d, J = 13.6 Hz, 1 H), 1.38-1.25 (m, 6 H); ¹³C NMR (CDCl3, 100 MHz): δ = 165.7, 165.5, 160.3, 156.7, 144.2, 136.2, 133.5, 129.1, 128.1, 127.5, 126.9, 126.0, 110.6, 79.3, 63.4, 63.2, 60.6, 58.9, 56.8, 53.9, 38.6, 36.7, 13.9, 13.8; HRMS: m/z [M + H]+ calcd for C28H30N6O9: 594.2074; found: 595.2147.
Compound 7g: Yield: 56%; white solid; mp 233-234 ˚C; IR (KBr): 3448, 2979, 2935, 2825, 1950, 1754, 1721, 1585, 1558, 1497, 1465, 1417, 1372, 1301, 1277, 1252, 1213, 1168, 1141, 1110, 1073, 1029, 986, 961, 910, 862, 828
cm-¹; ¹H NMR (CDCl3, 400 MHz): δ = 7.83 (d, J = 8.0 Hz, 1 H), 7.47 (d, J = 8.0 Hz, 1 H), 6.94-6.88 (m, 3 H), 5.45 (d, J = 16.0 Hz, 1 H), 4.88 (d, J = 16.0 Hz, 1 H), 4.68-4.39 (m, 4 H), 4.37-4.26 (m, 6 H), 2.94 (d, J = 14.0 Hz, 1 H), 2.88 (d, J = 14.0 Hz, 1 H), 1.38-1.30 (m, 6 H); ¹³C NMR (CDCl3, 150 MHz): δ = 165.7, 165.5, 156.9, 156.7, 139.9, 139.4, 136.8, 136.3, 130.8, 129.3, 129.0, 128.0, 127.3, 100.6, 79.4, 76.2, 63.2, 63.1, 60.0, 59.6, 53.8, 49.7, 46.0, 13.4, 13.8; HRMS: m/z [M + H]+ calcd for C27H28IN5O6: 645.1084; found: 646.1157.
Compound 7h: Yield: 82%; white solid; mp 212-213 ˚C; IR (KBr): 3448, 3066, 2960, 2930, 2851, 2153, 1772, 1652, 1587, 1544, 1461, 1419, 1368, 1318, 1254, 1223, 1157, 1098, 1098, 1077, 1027, 987, 919, 905, 859 cm-¹; ¹H NMR (CDCl3, 400 MHz): δ = 7.44 (d, J = 7.6 Hz, 2 H), 7.29-7.20 (m, 4 H), 6.93 (d, J = 7.6 Hz, 2 H), 5.73 (d, J = 16.0 Hz, 1 H), 4.84 (d, J = 16.0 Hz, 1 H), 4.70 (d, J = 14.4 Hz, 1 H), 4.62 (d, J = 14.4 Hz, 1 H), 4.60 (d, J = 16.4 Hz, 1 H), 4.49 (d, J = 16.4 Hz, 1 H), 4.38-4.25 (m, 6 H), 3.02 (d, J = 13.2 Hz, 1 H), 2.87 (d, J = 13.2 Hz, 1 H), 1.38-1.26 (m, 6 H), 0.30 (s, 9 H); ¹³C NMR (CDCl3, 150 MHz): δ = 166.1, 165.8, 157.1, 156.6, 138.5, 136.6, 132.4, 130.3, 129.2, 128.9, 128.2, 128.0, 127.5, 127.3, 123.9, 102.3, 99.6, 80.1, 76.1, 63.3, 63.1, 60.4, 59.5, 54.0, 45.7, 42.5, 14.0, 13.9; HRMS: m/z [M + H]+ calcd for C32H37N5O6Si: 615.2513; found: 616.2586.
Compound 7i: Yield: 58%; white solid; mp 288-289 ˚C; IR (KBr): 3424, 3059, 2983, 2930, 2846, 1739, 1721, 1588, 1545, 1460, 1420, 1368, 1315, 1259, 1224, 1172, 1148, 1080, 1026, 984, 917, 905, 854, 802 cm-¹; ¹H NMR (CDCl3, 400 MHz): δ = 8.63 (d, J = 8.4 Hz, 1 H), 7.90-7.84 (m, 2 H), 7.65-7.45 (m, 5 H), 7.33-7.29 (m, 2 H), 7.25-6.97 (m, 3 H), 6.95-5.90 (m, 2 H), 5.95 (d, J = 16.0 Hz, 1 H), 4.90 (d, J = 16.0 Hz, 1 H), 4.75-4.63 (m, 4 H), 4.57-4.26 (m, 6 H), 3.06 (d, J = 13.6 Hz, 1 H), 2.97 (d, J = 13.6 Hz, 1 H), 1.38-1.25 (m, 6 H); ¹³C NMR (CDCl3, 150 MHz): δ = 165.9, 165.6, 156.9, 156.6, 137.8, 136.8, 133.3, 133.1, 132.3, 130.9, 130.3, 129.3, 128.9, 127.8, 127.5, 126.9, 126.5, 126.4, 125.3, 124.2, 120.7, 92.3, 91.6, 80.1, 75.9, 63.4, 63.3, 59.4, 53.9, 45.7, 42.8, 13.9 cm-¹. HRMS: m/z [M + H]+ calcd for C39H35N5O6: 669.2587; found: 670.2660.
Compound 7j: Yield: 25%; white solid; mp 177-179 ˚C; IR (KBr): 3066, 2956, 2922, 1737, 1716, 1460, 1416, 1266, 850, 750 cm-¹; ¹H NMR (CDCl3, 400 MHz): δ = 7.51-7.45 (m, 4 H), 7.32-7.29 (m, 2 H), 6.94 (d, J = 2.0 Hz, 2 H), 4.86 (d, J = 15.6 Hz, 2 H), 4.64 (d, J = 15.6 Hz, 2 H), 4.60 (d, J = 14.0 Hz, 2 H), 4.39-4.28 (m, 6 H), 2.90 (s, 2 H), 1.38-1.25 (m, 6 H); ¹³C NMR (CDCl3, 100 MHz): δ = 165.8, 165.6, 157.0, 140.5, 136.2, 130.0, 129.1, 128.0, 125.0, 122.8, 80.3, 75.9, 63.3, 59.9, 53.2, 45.5, 29.7, 14.0; HRMS: m/z [M + H]+ calcd for C28H28F3N5O6: 587.1992; found: 588.2064.
Compound 7k: Yield: 65%; white solid; mp136-139 ˚C; IR (KBr): 3053, 2992, 2966, 2906, 1761, 1715, 1416, 1415, 1254, 820, 739 cm-¹; ¹H NMR (CDCl3, 400 MHz): δ = 7.49-7.46 (m, 2 H), 7.29-7.26 (m, 2 H), 7.01 (d, J = 7.6 Hz, 2 H), 6.75 (d, J = 8.0 Hz, 2 H), 4.86 (d, J = 16.0 Hz, 2 H), 4.64 (d, J = 16.0 Hz, 2 H), 4.37-4.27 (m, 6 H), 2.84 (s, 2 H), 2.27 (s, 3 H), 1.38-1.30 (m, 6 H); ¹³C NMR (CDCl3, 100 MHz): δ = 166.0, 165.7, 156.9, 136.8, 136.2, 133.4, 130.0, 128.9, 128.7, 128.0, 80.3, 76.0, 63.2, 63.1, 59.8, 53.5, 45.4, 21.0, 14.0, 13.9; HRMS: m/z [M + H]+ calcd for C28H31N5O6: 533.2274; found: 534.2347.
Compound 7l: Yield: 72%; white solid; mp 190-192 ˚C; IR (KBr): 3068, 2981, 2954, 2841, 1766, 1738, 1719, 1466, 1421, 1226, 736 cm-¹; ¹H NMR (CDCl3, 400 MHz): δ = 7.47-7.43 (m, 2 H), 7.27-7.24 (m, 2 H), 6.12 (s, 2 H), 4.86 (d, J = 16.0 Hz, 2 H), 4.65 (d, J = 15.6 Hz, 4 H), 4.38-4.29 (m, 6 H), 3.81 (s, 6 H), 3.79 (s, 3 H), 2.81 (s, 2 H), 1.38-1.31 (m, 6 H); ¹³C NMR (CDCl3, 100 MHz): δ = 165.8, 165.5, 156.9, 152.5, 136.6, 136.2, 131.8, 129.7, 127.8, 105.7, 80.2, 75.8, 63.2, 63.1, 60.6, 59.6, 55.8, 54.0, 45.3, 13.9, 13.8; HRMS: m/z [M + H]+ calcd for C30H35N5O9: 609.2435; found: 610.2508.

19

Crystal data for compound 7a: C27H29N5O6; MW = 519.55; monoclinic; a = 15.655(4), b = 8.752(2), c = 19.427(5) Å, β = 110.550(5)˚; V = 2492.4(11) ų; T = 292(2) K; space group P21/n; Z = 4; µ(Mo-Kα) = 0.100 mm-¹; 13703 reflections measured, 4889 unique (R int = 0.0476) which were used in all calculations. The final wR2 (F 2) was 0.1980 (all data).
For compound 7b: C29H33N5O6; MW = 547.60; monoclinic; a = 9.9597(9), b = 23.109(2), c = 12.4028(11) Å, β = 101.193(2)˚; V = 2800.3(4) ų; T = 292(2) K; space group P21/c; Z = 4; µ(Mo-Kα) = 0.092 mm-¹; 14003 reflections measured, 4926 unique (R int = 0.0343) which were used in all calculations. The final wR2 (F 2) was 0.1755 (all data).
For compound 7c: C29H33N5O8; MW = 579.60; monoclinic; a = 8.1464(6), b = 23.9524(17), c = 15.0281(11) Å, β = 104.7310(10)˚; V = 2836.0(4) ų; T = 292(2) K; space group P21/n; Z = 4; µ(Mo-Kα) = 0.100 mm-¹; 33110 reflections measured, 6772 unique (R int = 0.0987) which were used in all calculations. The final wR2 (F 2) was 0.1729 (all data).
For compound 7d: C27H27Br2N5O6; MW = 677.36; triclinic; a = 9.136(3), b = 10.144(3), c = 15.028(4) Å, α = 90.784(5)˚, β = 94.628(5)˚, γ = 94.984(5)˚; V = 1382.6(7) ų; T = 292(2) K; space group P1, Z = 2; µ(Mo-Kα) = 2.983 mm-¹; 13279 reflections measured, 5386 unique (R int = 0.1158) which were used in all calculations. The final wR2 (F 2) was 0.1795 (all data).
For compound 7e: C29H32N6O8; MW = 592.61; monoclinic; a = 7.9571(4), b = 15.6173(6), c = 22.8959(10) Å, β = 94.0820(10)˚; V = 2838.0(2) ų; T = 292(2) K; space group P21/c; Z = 4; µ(Mo-Kα) = 0.103 mm-¹; 21931 reflections measured, 4992 unique (R int = 0.0254) which were used in all calculations. The final wR2 (F 2) was 0.1761 (all data).
For compound 7f: C56H64N12O19; MW = 1209.19; tetragonal; a = 15.9660(6), b = 15.9660(6), c = 11.1270(9) Å, α = β = γ = 90.00˚; V = 2836.4(3) ų; T = 292(2) K; space group P43; Z = 2; µ(Mo-Kα) = 0.108 mm-¹; 32120 reflections measured, 6183 unique (R int = 0.1055) which were used in all calculations. The final wR2 (F 2) was 0.1147 (all data).
For compound 7g: C27H28IN5O6; MW = 645.44; monoclinic; a = 9.0743(10), b = 25.339(3), c = 11.6956(13) Å, β = 90.212(2)˚; V = 2689.2(5) ų; T = 292(2) K; space group P21/c; Z = 4; µ(Mo-Kα) = 1.242 mm-¹; 30097 reflections measured, 5852 unique (R int = 0.0924) which were used in all calculations. The final wR2 (F 2) was 0.1632 (all data).
For compound 7j: C28H28F3N5O6; MW = 587.55; triclinic; a = 9.2056(13), b = 12.8972(18), c = 13.3762(19) Å, α = 113.437(2)˚, β = 98.874(2)˚, γ = 99.525(2)˚; V = 1393.8(3) ų; T = 292(2) K; space group P1; Z = 2; µ(Mo-Kα) = 0.113 mm-¹; 14646 reflections measured, 5445 unique (R int = 0.0559) which were used in all calculations. The final wR2 (F 2) was 0.1554 (all data).
For compound 7k: C28H31N5O6; MW = 533.58; orthorhombic; a = 18.049(4), b = 18.263(4), c = 8.0492(17) Å, α = β = γ = 90.00˚; V = 2653.3(10) ų; T = 292(2) K; space group Pna21; Z = 4; µ(Mo-Kα) = 0.096 mm-¹; 26452 reflections measured, 3099 unique (R int = 0.0885) which were used in all calculations. The final wR2 (F 2) was 0.1101 (all data).
For compound 7l: C30H35N5O9; MW = 613.63; monoclinic; a = 8.9216(5), b = 29.5203(17), c = 11.5079(6) Å, β = 90.5000(10)˚; V = 3030.7(3) ų; T = 292(2) K; space group P21/n; Z = 4; µ(Mo-Kα) = 0.101 mm-¹; 23651 reflections measured, 5919 unique (R int = 0.0768) which were used in all calculations. The final wR2 (F 2) was 0.2164 (all data).
CCDC-724320 (7a); CCDC-724321 (7b); CCDC-724322 (7c); CCDC-724323 (7d); CCDC-724324 (7e); CCDC-724325 (7f); CCDC-724326 (7g); CCDC-724327 (7j); CCDC-724328 (7k); CCDC-724329 (7l). These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; email: deposit@ccdc.cam.ac.uk].