PDF《Supporting Information》

2 mol%) in THF (330 mL) and N-methylpyrrolidone (33 mL) was added decylmagnesium bromide (1.0 M in Et2O, 96.7 mL, 96.7 mmmol, 1.3 mol amt.) dropwise at room temperature. The color immediately changed into dark brown and the reaction was exothermic. After stirring for

2 h at ambient temperature, the reaction was quenched with water. The organic layer was extracted with ethyl acetate and washed with water and brine. After the solvent of combined organic layer was removed in vacuo, the crude material was purified by silica gel column chromatography (hexane:chloroform = 97:3) to afford the titled compound (17.0 g, 57.0 mmol, 77%) as white solid. The spectral data of this compound was identical to the literature previously.2 General procedure of homo-coupling reaction: 6,6'

-Didecyl-3,3'

-dimethoxy-2,2'

-binaphthalene (for synthesis of C10CDNFCVW) To a solution of 7-decyl-2-methoxynaphthalene (7.46 g, 25.0 mmol) in THF (100 mL) was added 1.62 M n-BuLi in hexane (17.0 mL, 27.5 mmol, 1.1 mol amt.) at

0 °C. After stirring at

0 °C for

2 h, Fe(acac)3 (9.71 g, 27.5 mmol, 1.1 mol amt.) was added at

0 °C 73% 1) n- BuLi (1.1 eq)

0 °C,

2 h 2) Fe(acac)3 (1.1 eq) 0°C to rt,

10 h OMe MeO H21C10 C10H21 OMe H21C10 OMe C10H21MgBr (1.3 eq) Fe(acac)3 (2 mol%) THF/ NMP rt,

2 h C10H21 77% OMe TfO S4 and the resultant mixture was stirred at room temperature for

10 h. After the reaction finished, the crude material was passed through a short pad of Celite? to remove the inorganic salt. After removing the solvent in vacuo, the crude material was purified by silica gel column chromatography (hexane:chloroform = 90:10) to afford the titled compound (5.43 g, 9.13 mmol, 73%) as white solid. M.p.: 68.4C71.5 °C.

1 H NMR (400 MHz, CDCl3): δ 0.89 (t, J = 6.8 Hz, 6H, CH3), 1.26C1.40 (m, 28H, (CH2)7), 1.70 (quin, J = 7.2 Hz, 4H, ArCH2CH2), 2.76 (t, J = 7.2 Hz, 4H, ArCH2), 3.86 (s, 6H, OCH3), 7.16 (s, 2H, ArH), 7.19 (d, J = 8.4 Hz, 2H, ArH), 7.56 (s, 2H, ArH), 7.68C7.71 (m, 4H, ArH).

13 C NMR (150 MHz, CDCl3): δ 14.3, 22.9, 29.2 (two carbons), 29.75, 29.82 (two carbons), 31.6, 32.1, 36.4, 55.8, 105.1, 125.2, 125.4, 127.2, 127.6, 129.2, 130.1, 134.6, 141.0, 156.5. TOF HRMS (APCI): Calcd for C42H59O2 [M+H] 595.4515, found 595.4537. Anal. Calcd for C42H58O2: C, 84.79;

H, 9.83. Found: C, 84.85;

H, 9.72. 7,7'

-Didecyl-3,3'

-dimethoxy-2,2'

-binaphthalene (for synthesis of C10CDNFCVV) White solid. Yield: 66%. M.p.: 65.4C66.4 °C.

1 H NMR (400 MHz, CDCl3): δ 0.88 (t, J = 6.8 Hz, 6H, CH3), 1.26C1.35 (m, 28H, (CH2)7), 1.69 (quin, J = 7.6 Hz, 4H, ArCH2CH2), 2.74 (t, J = 7.6 Hz, 4H, ArCH2), 3.86 (s, 6H, OCH3), 7.19 (s, 2H, ArH), 7.30 (d, J = 8.4 Hz, 2H, ArH), 7.55 (s, 2H, ArH), 7.68 (s, 2H, ArH), 7.70 (d, J = 8.4 Hz, 2H, ArH).

13 C NMR (150 MHz, CDCl3): δ 14.3, 22.9, 29.48, 29.51, 29.7, 29.80 (two carbons), 31.7, 32.1, 36.1, 55.8, 105.3, 126.3, 126.4, 127.9, 129.0, 129.9, 130.1, 132.8, 138.3, 155.9. TOF HRMS (APCI): Calcd for C42H59O2 [M+H] 595.4515, found 595.4509. Anal. Calcd for C42H58O2: C, 84.79;

H, 9.83. Found: C, 84.73;

H, 9.56. OMe MeO C10H21 C10H21 1) n- BuLi (1.1 eq)

0 °C,

2 h 2) Fe(acac)3 (1.1 eq) 0°C to rt,

12 h OMe C10H21 66% S5 General procedure of demethylation reaction: 6,6'

-Didecyl-2,2'

-binaphthalene-3,3'

-diol (for synthesis of C10CDNFCVW) To a solution of 6,6'

-didecyl-3,3'

-dimethoxy-2,2'

-binaphthalene (4.46 g, 7.50 mmol) in dichloromethane (30 mL) was added 1.0 M BBr3 in dichloromethane (16.5 mL, 16.5 mmol, 2.2 mol amt.) at