ࡱ>       M Rbjbj==ByWWh>lVVVV~~~8v    q P$." N$i~]' | ]]=VV K< ===]dV (~ =]=@=}*T~} `P'0}R 0 }$L$=VVVV Synthesis and Self-aggregation of Isomeric Cyclic Alkynes Containing Helicene Keiichi Nakamura, Hitoshi Okubo, and Masahiko Yamaguchi* Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences Tohoku University Aoba, Sendai 980-8578, Japan Supporting Information Melting points were determined with a Yanagimoto micro melting point apparatus without correction. Optical rotations were measured on a JASCO DIP-340 digital polarimeter. IR spectra were measured on JASCO FT/ IR-400 spectrophotometer. UV spectra were measured on BECKMAN DU 640. 1H-NMR and 13C-NMR spectra were recorded on a Varian Mercury (400 MHz) or a Brucker AM-600 (600 MHz) with tetramethylsilane as an internal standard, and the abbreviations of signal patterns are follows: s, singlet; d, doublet; t, triplet; quin, quintet; m, multiplet. High-resolution mass spectra were recorded on a JEOL JMS-DX-303 or JMS-AX-500 spectrometer. FAB mass spectra were measured on a JEOL JMS-DX-303 or JMS-AX-500 spectrometer by using m-nitrobenzyl alcohol matrix. MALDI TOF-MS spectra were recorded on a Perseptive Biosystems VoyagerTM DE using a-cyano-4-hydroxycinnamic acid as the matrix. CD spectra were measured on a JASCO J-720 spectropolarimeter. Vapor pressure osmometry (VPO) was conducted with Corona 117 molecular weight apparatus. Gel permeation chromatography (GPC) was conducted with Recycling Preparative HPLC LC-908 or LC-918 (Japan Analytical Industry, Co. Ltd.). Dimethyl (M)-1,12-Dimethylbenzo[c]phenanthrene-5,8-dicarboxylate. Under an argon atmosphere, a mixture of (M)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylic acid (2.06 g, 5.37 mmol), and thionyl chloride (40 mL) was heated at reflux for 3 h. After cooled to room temperature, the solvent was removed under a reduced pressure, and the resulted acid chloride was azeotropically dried by adding dichloromethane (30 mL) and evaporating twice. Then dry dichloromethane (40 mL), triethylamine (4.5 mL), and methanol (0.65 mL) were added at 0 C. After 2 h at room temperature, the reaction was quenched by adding saturated aqueous ammonium chloride, and the organic materials were extracted with chloroform. The organic layer was washed with water and brine, dried over magnesium sulfate. After removing the solvents under a reduced pressure, silica gel chromatography gave the title compound (1.61 g, 5.08 mmol, 95%). Mp 242-243 C (n-hexane-ethyl acetate). [a]D23  310 (c 0.67, CHCl3). HRMS m/z Calcd for C22H20O4: 372.1362. Found: 372.1369. Anal. (C22H20O4) Calcd for: C, 77.40; H, 5.41%. Found: C, 76.36; H, 5.67%. UV-VIS (MeOH) l max (e) 314 nm (3.2x103). IR (KBr) 1717 cm-1. 1H-NMR (600 MHz, CDCl3) d 1.88 (6H, s), 4.07 (6H, s), 7.44 (2H, d, J = 6.9 Hz), 7.68 (2H, dd, J = 6.9, 8.3 Hz), 8.51 (2H, s), 8.84 (2H, d, J = 8.3 Hz). 13C-NMR (150 MHz, CDCl3-CD3OD) d 23.4, 52.4, 123.1, 127.0, 127.8, 128.8, 129.1, 129.8, 130.6, 131.3, 131.3, 136.8, 167.7. (M)-1,12-Dimethylbenzo[c]phenanthrene-5,8-dimethanol. Under an argon atmosphere, to a solution of dimethyl (M)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylate (1.10 g, 296 mmol) in dry tetrahydrofuran (20 mL) was added lithium aluminum hydride (224 mg, 5.90 mmol) at 0 C. The mixture was stirred for 2 h at room temperature. Then methanol, water, and hydrochloric acid were added successively, and the organic materials were extracted with chloroform. The organic layer was washed with water and brine, and dried over magnesium sulfate. The solvents were evaporated under a reduced pressure, and recrystallization gave the title compound (933 mg, 2.95 mmol, 100%). Mp > 300 C (chloroform-methanol). [a]D27 +186 (c 0.190, CHCl3-MeOH, 1:1). HRMS m/z Calcd for C22H20O2: 316.1463. Found: 316.1465. Anal. (C22H20O2) Calcd for: C, 83.52; H, 6.37%. Found: C, 83.68; H, 6.16%. UV-VIS (MeOH) l max (e) 333 (8.4x103), 303 nm (1.4x104). IR (KBr) 3286 cm-1. 1H-NMR (600 MHz, CDCl3-CD3OD) d 1.66 (6H, s), 4.32 (2H, s), 4.96 (2H, d, J = 13.3 Hz), 5.03 (2H, d, J = 13.2 Hz), 7.14 (2H, d, J = 7.0 Hz), 7.33 (2H, dd, J = 7.0, 8.0 Hz), 7.61 (2H, s), 7.84 (2H, d, J = 8.1 Hz). 13C-NMR (150 MHz, CDCl3-CD3OD) d 22.7, 62.0, 120.2, 123.6, 124.7, 125.3, 27.6, 129.9, 131.2, 131.2, 135.2, 136.2. (M)-1,12-Dimethylbenzo[c]phenanthrene-5,8-dicarbaldehyde. To a solution of (M)-1,12-dimethylbenzo[c]phenanthrene-5,8-dimethanol (1.37 g, 4.35 mmol) in dichloromethane (30 mL) was added activated manganese(IV) oxide (7.56 g, 87.2 mmol). The mixture was vigorously stirred for 11 h at room temperature. Then, the reaction mixture was filtered through Celite pad, and the pad was washed 3 times with dichloromethane. Solvents were evaporated under a reduced pressure, and silica gel chromatography gave the title compound. Mp 256-258 C (n-hexane-CHCl3). [a]D22  380 (c 0.47, CHCl3). HRMS m/z calc. for C22H16O2: 312.1150. Found: 312.1148. Anal. (C22H16O2) Calcd for: C, 46.20; H, 2.58; Br; 51.22%. Found: C; 46.22, H; 2.71, Br; 51.33%. UV-VIS (CHCl3) lmax (e) 323 nm (6.8x104). IR (KBr) 1682 cm-1. 1H-NMR (400 MHz, CDCl3) d 1.91 (6H, s), 7.52 (2H, d, J = 7.3 Hz), 7.78 (2H, dd, J = 7.3, 8.3 Hz), 8.40 (2H, s), 9.27 (2H, d, J = 8.3 Hz), 10.53 (2H, s). 13C-NMR (100 MHz, CDCl3) d 23.6, 122.5, 129.2, 129.3, 129.9, 130.1, 131.3, 131.4, 134.3, 137.0, 137.2, 192.3. (M)-5,8-Bis(2,2-dibromoethenyl)-1,12-dimethylbenzo[c]phenanthrene. Under an argon atmosphere, to a solution of triphenylphosphine (4.08 g, 15.5 mmol) in dichloromethane (10 mL) was added tetrabromomethane (2.58 mg, 7.78 mmol) at 0 C. After stirred for 45 min at the temperature, (M)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarbaldehyde (810 mg, 2.59 mmol) in dichloromethane (10 mL) was added dropwise. The mixture was stirred for 3.5 h at the temperature. Then, the solvent was evaporated under a reduced pressure, and silica gel chromatography gave the title compound (1.61 g, 2.59 mmol, 100%). Mp 224-225 C (n-hexane-CHCl3). [a]D23  290 (c 0.66, CHCl3). HRMS m/z Calcd for C26H16Br4 619.7985. Found: 619.7974. Anal. (C26H16Br4) Calcd for: C, 46.20; H, 2.58; Br; 51.22%. Found: C; 46.22, H; 2.71, Br; 51.33%. UV-VIS (CHCl3) lmax (e) 314 nm (6.3x104). IR (KBr) 2362 cm-1. 1H-NMR (400 MHz, CDCl3) d 1.95 (6H, s), 7.44 (2H, d, J = 7.1 Hz), 7.63 (2H, dd, J = 7.1, 8.1 Hz), 7.93 (2H, d, J = 1.1 Hz), 7.95 (2H, d, J = 8.1 Hz), 8.00 (2H, d, J = 1.1 Hz). 13C-NMR (100 MHz, CDCl3) d 23.7, 93.3, 121.6, 126.0, 126.2, 126.4, 128.8, 130.0, 130.8, 131.2, 132.6, 135.6, 136.9, 181.3. (M)-5,8-Bis(bromoethynyl)-1,12-dimethylbenzo[c]phenanthrene. Under an argon atmosphere, to a solution of (M)-5,8-bis(2,2-dibromoethenyl)-1,12-dimethylbenzo[c]phenanthrene (1.46 g, 2.35 mmol) in tetrahydrofuran (30 mL) was added sodium bis(trimethylsilyl)amide in tetrahydrofuran (1.0 M solution, 7.1 mL, 7.1 mmol) dropwise at 100 C. After stirred for 10 min at the temperature, saturated aqueous ammonium chloride was added. The organic materials were extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated under a reduced pressure, and silica gel chromatography gave the title compound (1.09 g, 2.36 mmol, 100%). Mp 224-225 C (n-hexane-CHCl3). [a]D20  389 (c 1.06, CHCl3). Anal. (C24H14Br2) Calcd C, 62.37; H, 3.05; Br, 34.58%. Found C, 62.41; H, 3.03; Br, 34.56%. 1H-NMR (400 MHz, CDCl3) d 1.90 (6H, s), 7.44 (2H, d, J = 6.8 Hz), 7.65 (2H, dd, J = 6.8, 7.6 Hz), 7.96 (2H, s), 8.36 (2H, d, J = 7.6 Hz). 13C-NMR (100 MHz, CDCl3) d 23.3, 54.8, 78.5, 119.8, 123.4, 126.4, 126.9, 129.1, 130.0, 130.5, 130.7, 132.3, 136.7. (M)-5,8-Diethynyl-1,12-dimethylbenzo[c]phenanthrene (M)-4. Under an argon atmosphere, to a solution of (M)-5,8-bis(bromoethynyl)-1,12-dimethylbenzo[c]phenanthrene (1.09 g, 2.36 mmol) in tetrahydrofuran (15 mL) was added n-butyllithium in hexane (1.56 M solution, 3.5 mL, 5.46 mmol) dropwise at 100 C. After stirred for 25 min at the temperature, the reaction mixture was warmed to room temperature, and diluted with n-hexane. Saturated aqueous ammonium chloride was added, and the organic materials were extracted with ethyl acetate. Then, the organic layer was washed with water and brine, and dried over magnesium sulfate. The solvents were evaporated under a reduced pressure, and silica gel chromatography gave (M)-4 (699 mg, 2.30 mmol, 96%). Mp 141-144 C (decomp., n-hexane-CHCl3). [a]D27  258 (c 1.16, CHCl3). Anal. (C24H16) Calcd for: C, 94.70; H, 5.30%. Found: C, 94.37; H, 5.43%. HRMS m/z Calcd for C24H16: 304.1252. Found: 304.1240. UV-VIS (CHCl3) lmax (e) 317 nm (7.8x104). IR (KBr) 3290, 2100 cm-1. 1H-NMR (400 MHz, CDCl3) d 1.92 (6H, s), 3.55 (2H, s), 7.45 (2H, d, J = 6.8 Hz), 7.66 (2H, dd, J = 6.8, 8.0 Hz), 8.02 (2H, s), 8.43 (2H, d, J = 8.0 Hz). 13C-NMR (100 MHz, CDCl3) d 23.4, 81.9, 82.5, 119.3, 123.5, 126.7, 126.9, 129.1, 130.3, 130.6, 130.7, 132.3, 136.7. (M)-1,12-Dimethyl-8-ethynyl-5-(trimethylsilylethynyl)benzo[c]phenanthrene and (M)-5,8-Bis(trimethylsilylethynyl)-1,12-dimethylbenzo[c]phenanthrene. Under an argon atmosphere, to a solution of (M)-7 (712 mg, 2.34 mmol) in tetrahydrofuran (15 mL) was added n-butyllithium in hexane (1.56 M solution, 1.65 mL, 2.57 mmol) dropwise at 100 C. After stirred for 50 min at the temperature, trimethylsilyl chloride (0.45 mL, 3.6 mmol) was added. The mixture was stirred for 15 min at the temperature, when saturated aqueous ammonium chloride and ethyl acetate were added. Stirring was continued for 15 min at room temperature. The organic materials were extracted with ethyl acetate. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. The solvents were evaporated under a reduced pressure, and silica gel chromatography gave (M)-1,12-dimethyl-8-ethynyl-5-(trimethylsilylethynyl)benzo[c]phenanthrene (645 mg, 1.71 mmol, 73%) and (M)-5,8-bis(trimethylsilylethynyl)-1,12-dimethylbenzo[c]phenanthrene (114 mg, 0.255 mmol, 11%). (M)-7 (90. mg, 0.30 mmol, 13%) was recovered. (M)-1,12-Dimethyl-8-ethynyl-5-trimethylsilylethynylbenzo[c]phenanthrene: Mp 224-225 C (n-hexane-CHCl3). [a]D22  326 (c 2.62, CHCl3). MS (EI, 70 eV) m/z 376 (M+, 100 %), 361 (M+ Me, 27). HRMS m/z Calcd for C27H24Si: 376.1647. Found: 376.1619. Anal. (C27H24Si) Calcd for: C, 86.12; H, 6.42%. Found: C, 85.83; H, 6.55%. 1H-NMR (400 MHz, CDCl3) d 0.37 (9H, s), 1.91 (3H, s), 1.92 (3H, s), 3.55 (1H, s), 7.44 (2H, d, J = 6.8 Hz), 7.65 (1H, dd, J = 6.8, 7.2 Hz), 7.66 (1H, dd, J = 6.8, 8.0 Hz), 8.01 (2H, s), 8.41 (1H, d, J = 7.2 Hz) 8.43 (1H, d, J = 8.0 Hz). 13C-NMR (100 MHz, CDCl3) d 0.3, 23.2, 23.3, 81.8, 82.3, 100.1, 103.0, 119.1, 120.1, 123.3, 123.5, 126.4, 126.7, 126.7, 128.9, 128.9, 129.7, 130.2, 130.6, 130.6, 130.7, 132.1, 132.2, 136.6, 136.6. (M)-5,8-Bis(trimethylsilylethynyl)-1,12-dimethylbenzo[c]phenanthrene: Mp 224-225 C (n-hexane-CHCl3). [a]D26  309 (c 0.72, CHCl3). MS (EI, 70 eV) m/z 448 (M+, 100 %), 433 (M+-Me, 17). HRMS m/z Calcd for C30H32Si2: 448.2043. Found: 448.2010. IR (KBr) 2959, 2148 cm-1. 1H-NMR (400 MHz, CDCl3) d 0.37 (18H, s), 1.90 (6H, s), 7.42 (2H, d, J = 6.8 Hz), 7.64 (2H, dd, J = 6.8, 7.6 Hz), 7.97 (2H, s), 8.40 (2H, d, J = 7.6 Hz). 13C-NMR (100 MHz, CDCl3) d 0.4, 23.3, 100.1, 103.1, 120.1, 123.6, 126.4, 126.7, 129.0, 129.8, 130.8, 130.8, 132.2, 136.7. Decyl (M)-3-[1',12'-Dimethyl-8'-(trimethylsilylethynyl)benzo[c]phenanthryl-5'-ethynyl]-5-trifluoromethanesulfoxybenzoate (M)-5. Under an argon atmosphere, a mixture of decyl 3,5-bis(trifluoromethanesulfonyloxy)benzoate (1.54 g, 2.75 mmol), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (18 mg, 0.017 mmol), cuprous iodide (39 mg, 0.21 mmol), trimesitylphosphine (40 mg, 0.10 mmol), triphenylphosphine (27 mg, 0.10 mmol), tetrabutylammonium iodide (509 mg, 1.38 mmol), diisopropylethylamine (0.4 mL), and N,N-dimethylformamide (8 mL) was freeze-evacuated three times in flask A. In flask B, a solution of (M)-1,12-dimethyl-8-ethynyl-5-trimethylsilylethynylbenzo[c]phenanthrene (259 mg, 0.689 mmol) in N,N-dimethylformamide (2 mL) was freeze-evacuated three times, and was added to flask A dropwise. The mixture was stirred for 30 min at room temperature. The reaction was quenched by adding saturated aqueous ammonium chloride, and the organic materials were extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate. The solvents were evaporated under a reduced pressure, and separation by recycling GPC gave (M)-5 (513 mg, 0.653 mmol, 95%). Mp 88-89 C (MeOH-toluene). [a]D27  337 (c 1.11, CHCl3). HRMS m/z Calcd for C45H47 F3O5SSi: 784.2866. Found: 784.2846. UV-VIS (CHCl3) lmax (e) 335 nm (8.6x104). IR (KBr) 2926, 2149, 1729 cm-1. CD (CHCl3, 28 mM) lmax (De) 383 nm ( 36), 331 (22), 296 ( 17), 262 (47). Anal. (C45H47F3O5SSi) Calcd for: C, 68.85; H, 6.03; S, 4.08%. Found: C, 68.46; H, 6.01; S, 4.71%. 1H-NMR (400 MHz, CDCl3) d 0.39 (9H, s) , 1.20-1.50 (14H, m), 1.82 (2H, quin, J = 6.8 Hz), 1.93 (3H, s), 1.94 (3H, s), 4.40 (2H, t, J = 6.8 Hz), 7.46 (1H, d, J = 7.2 Hz), 7.47 (1H, d, J = 7.6 Hz), 7.67 (1H, dd, J = 7.2, 8.0 Hz), 7.70 (1H, dd, J = 7.6, 8.0 Hz), 7.75 (1H, dd, J = 1.4, 2.6 Hz), 7.93 (1H, dd, J = 1.6, 2.4 Hz), 8.02 (1H, s), 8.07 (1H, s), 8.35 (1H, t, J = 1.4 Hz), 8.43 (1H, d, J = 8.0 Hz), 8.43 (1H, d, J = 8.0 Hz). 13C-NMR (100 MHz, CDCl3) d 0.3, 14.2, 22.8, 23.3, 26.1, 28.7, 29.4, 29.4, 29.6, 32.0, 66.3, 91.0, 91.4, 100.3, 102.9, 118.9, 120.4, 122.0, 123.2, 123.6, 126.2, 126.8, 126.9, 126.9, 127.9, 129.1, 129.2, 129.6, 130.1, 130.7, 130.8, 131.8, 132.3, 132.4, 133.2, 136.7, 136.8, 149.1, 164.0. Decyl (M)-3,5-Bis[1',12'-dimethyl-8'-trimethylsilylethynylbenzo[c]phenanthryl-5'- ethynyl]benzoate. Under an argon atmosphere, a mixture of decyl 3,5-bis(trifluoromethane sulfonyloxy)benzoate (140 mg, 0.251 mmol), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (13 mg, 0.013 mmol), cuprous iodide (29 mg, 0.15 mmol), trimesitylphosphine (15 mg, 0.038 mmol), triphenylphosphine (10 mg, 0.037 mmol), tetrabutylammonium iodide (370 mg, 1.00 mmol), diisopropylethylamine (0.4 mL), and N,N-dimethylformamide (8 mL) was freeze-evacuated three times in flask A. In flask B, a solution of (M)-5 (190 mg, 0.505 mmol) in N,N-dimethylformamide (2 mL) was freeze-evacuated three times, and was added dropwise to flask A. The mixture was stirred for 1 h at room temperature. The reaction was quenched by adding saturated aqueous ammonium chloride, and the organic materials were extracted with chloroform. The organic layer was washed with brine, and dried over magnesium sulfate. The solvents were evaporated under a reduced pressure, and separation by recycling GPC gave the title compound (239 mg, 0.236 mmol, 94%). Mp 112-114 C (MeOH-toluene). [a]D28  504 (c 0.35, CHCl3). MS (FAB, NBA) m/z 1010 (M+ 1). UV-VIS (CHCl3) lmax (e) 335 nm (1.1x105). CD (CHCl3, 17 mM) lmax (De) 385 nm ( 36), 331 (21), 297 ( 16), 263 (43). IR (KBr) 1724 cm-1. Anal. (C71H70O2Si2) Calcd for: C, 84.31; H, 6.98%. Found: C, 84.06; H, 6.96%. 1H-NMR (400 MHz, CDCl3) d 0.39 (18H, s), 0.86 (3H, t, J = 7.2 Hz), 1.20-1.45 (12H, m), 1.45-1.55 (2H, m), 1.85 (2H, quin, J = 7.2 Hz), 1.94 (6H, s), 1.95 (6H, s), 4.42 (2H, t, J = 6.6 Hz), 7.46 (2H, d, J = 8.0 Hz), 7.48 (2H, d, J = 8.0 Hz), 7.67 (2H, t, J = 8.0 Hz), 7.71 (2H, t, J = 8.0 Hz) , 8.04 (2H, s), 8.08 (2H, s), 8.18 (1H, t, J = 1.6 Hz), 8.35 (2H, d, J = 1.2 Hz), 8.43 (2H, d, J = 8.0 Hz) , 8.53 (2H, d, J = 8.0 Hz). 13C-NMR (100 MHz, C6D6) d 0.5, 14.5, 23.3, 23.4 (2 peaks), 26.6, 29.3, 29.8, 29.9, 30.1, 30.1, 32.5, 65.9, 90.3, 93.6, 100.4, 104.3, 120.4, 121.2, 124.1, 124.2, 125.1, 127.2, 127.2, 127.3, 127.9, 129.4, 129.4, 130.5, 131.5, 131.5, 131.6, 132.5, 132.8, 132.8, 133.1, 137.2, 137.2, 138.5, 165.0. (M,M,M)-[3+2]Dialkyne Bistrimethylsilyl Derivative. Under an argon atmosphere, a mixture of (M)-5 (262 mg, 0.334 mmol), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (9 mg, 0.008 mmol), cuprous iodide (19 mg, 0.10 mmol), trimesitylphosphine (19 mg, 0.048 mmol), triphenylphosphine (13 mg, 0.050 mmol), tetrabutylammonium iodide (246 mg, 0.666 mmol), diisopropylethylamine (0.20 mL) and N,N-dimethylformamide (4 mL) was freeze-evacuated three times in flask A. In flask B, a solution of (M)-4 (51 mg, 0.17 mmol) in N,N-dimethylformamide (3 mL) was freeze-evacuated three times, and was added to flask A dropwise. The mixture was stirred for 1 h at room temperature. The reaction was quenched by adding saturated aqueous ammonium chloride, and the organic materials were extracted with chloroform. The organic layer was washed with brine, and dried over magnesium sulfate. The solvents were evaporated under a reduced pressure, and separation by recycling GPC gave the title compound (219 mg, 0.139 mmol, 83%). Mp 142-144 C (MeOH-toluene). [a]D27  433 (c 1.96, CHCl3). MS (FAB, NBA) m/z 1573 (M+). UV-VIS (CHCl3) lmax (e) 335 nm (1.2x105). CD (CHCl3, 21 mM) lmax (De) 387 nm ( 136), 332 (60), 297 ( 56), 263 (171). IR (CHCl3) 2149, 1724 cm-1. Anal. (C112H108O4Si2) Calcd for: C, 85.45; H, 6.91%. Found: C, 85.28; H, 6.79%. 1H-NMR (400 MHz, CDCl3) d 0.39 (18H, s), 0.86 (6H, t, J = 6.8 Hz), 1.20-1.45 (24H, m), 1.45-1.55 (4H, m), 1.86 (4H, quin, J = 7.2 Hz), 1.94 (6H, s), 1.95 (6H, s), 2.00 (6H, s), 4.43 (4H, t, J = 6.8 Hz), 7.46 (2H, d, J = 8.0 Hz), 7.47 (2H, d, J = 8.8 Hz), 7.51 (2H, d, J = 7.2 Hz), 7.67 (2H, dd, J = 7.6, 8.0 Hz), 7.72 (2H, t, J = 8.0 Hz), 7.74 (2H, dd, J = 7.6, 8.4 Hz), 8.04 (2H, s), 8.09 (2H, s), 8.15 (2H, s), 8.20 (2H, t, J = 2.0 Hz), 8.36 (2H, t, J = 2.0 Hz), 8.37 (2H, t, J = 2.0 Hz), 8.43 (2H, d, J = 7.6 Hz), 8.54 (2H, d, J = 8.8 Hz), 8.55 (2H, d, J = 8.4 Hz). 13C-NMR (100 MHz, CDCl3) d 0.4, 14.4, 22.9, 23.4, 23.4, 23.5, 26.3, 29.0, 29.5, 29.5, 29.8, 32.1, 65.9, 89.4, 89.4, 93.0 93.1, 100.2, 103.1, 119.7, 119.9, 120.3, 123.6, 123.7, 124.3, 124.3, 126.6, 126.9, 126.9, 127.0, 129.1, 129.2, 129.3, 129.8, 130.8, 130.9, 131.0, 131.5, 132.1, 132.2, 132.3, 136.7, 136.8, 136.9, 138.2, 165.3. (M,M,M)-[3+2]Dialkyne (M,M,M)-6. To a solution of (M,M,M)-[3+2]dialkyne bistrimethylsilyl derivative (127 mg, 0.0807 mmol) in tetrahydrofuran (3 mL) was added tetrabutylammonium fluoride (1.0 M solution, 0.20 mL, 0.20 mmol) at room temperature. After stirred for 2 h at the temperature, saturated aqueous ammonium chloride was added. The organic materials were extracted with chloroform. The organic layer was washed with brine, and dried over magnesium sulfate. The solvents were evaporated under a reduced pressure, and silica gel chromatography gave (M,M,M)-6 (115 mg, 80.4 mmol, 100%). Mp 137 139 C (toluene-methanol). [a]D23  580 (c 1.00, CHCl3). MS (FAB, NBA) m/z 1429 (M+). UV-VIS (CHCl3) lmax (e) 332 nm (1.8x105). CD (CHCl3, 18 mM) lmax (De) 386 nm ( 50), 331 (26), 297 ( 23), 263 (68). IR (KBr) 3303, 1721 cm-1. Anal. (C106H92O4) Calcd for: C, 89.04; H, 6.49%. Found: C, 88.72; H, 6.33%. 1H-NMR (400 MHz, CDCl3) d 0.86 (6H, t, J = 6.8 Hz), 1.20-1.45 (24H, m), 1.45-1.55 (4H, m), 1.86 (4H, quin, J = 7.2 Hz), 1.96 (12H, s), 1.99 (6H, s), 3.57 (2H, s), 4.43 (4H, t, J = 6.8 Hz), 7.47 (2H, d, J = 8.4 Hz), 7.49 (2H, d, J = 8.0 Hz), 7.51 (2H, d, J = 8.0 Hz), 7.67 (2H, dd, J = 7.6, 8.4 Hz), 7.73 (2H, t, J = 8.0 Hz), 7.74 (2H, t, J = 8.0 Hz), 8.08 (2H, s), 8.11 (2H, s), 8.15 (2H, s), 8.20 (2H, dd, J = 2.0, 1.6 Hz), 8.36 (2H, dd, J = 1.2, 1.6 Hz), 8.37 (2H, d, J = 2.0, 1.2 Hz), 8.45 (2H, d, J = 8.0 Hz), 8.54 (2H, d, J = 8.0 Hz), 8.55 (2H, d, J = 7.6 Hz). 13C-NMR (100 MHz, CDCl3) d 14.2, 22.8, 22.8, 23.3, 23.4, 26.2, 28.9, 29.3, 29.4, 29.7, 31.7, 32.0, 65.9, 81.8, 82.4, 89.3 (two peaks), 92.9, 93.0, 119.3, 119.7, 119.7, 123.4, 123.5, 123.5, 124.2, 126.7, 126.7, 126.8, 126.9, 129.1, 129.1, 129.2, 129.7, 129.7, 130.3, 130.7, 130.8, 130.8, 130.9, 131.4, 132.0, 132.1, 132.2, 136.7, 136.8, 136.8, 138.1, 165.2. (M,P,M)-[3+2]Dialkyne Bistrimethylsilyl Derivative. The title compound (131 mg, 0.0832 mmol, 82%) was prepared from (P)-4 (31 mg, 0.10 mmol) and (M)-5 (161 mg, 0.205 mmol) as was (M,M,M)-[3+2]dialkyne bistrimethylsilyl derivative. Mp 138141 C (toluene-methanol). [a]D24  107 (c 1.12, CHCl3). UV-VIS (CHCl3) lmax (e) 335 nm (2.0x105). CD (CHCl3, 16 mM) lmax (De) 400 nm (3.8), 379 ( 34), 329 (27), 297 ( 16), 259 (32). IR (CHCl3) 2149, 1724 cm-1. MALDI TOF-MS m/z Calcd for 12C11113CH108O4Si2: 1573.8. Found: 1574.1. 1H-NMR (400 MHz, CDCl3) d 0.39 (18H, s), 0.86 (6H, t, J = 6.6 Hz), 1.20-1. 54 (28H, m), 1.86 (4H, m), 1.94 (6H, s), 1.95 (6H, s), 2.00 (6H, s), 4.43 (4H, t, J = 6.8 Hz), 7.46 (2H, d, J = 8.1 Hz), 7.48 (2H, d, J = 8.4 Hz), 7.51 (2H, d, J = 6.8 Hz), 7.68 (2H, t, J = 7.6 Hz), 7.72 (2H, dd, J = 8.1, 9.3 Hz), 7.74 (2H, dd, J = 7.3, 9.3 Hz), 8.04 (2H, s), 8.09 (2H, s), 8.15 (2H, s), 8.20 (2H, t, J = 1.6 Hz), 8.36 (2H, t, J = 1.6 Hz), 8.37 (2H, t, J = 1.6 Hz), 8.43 (2H, d, J = 7.9 Hz), 8.54 (2H, d, J = 9.2 Hz), 8.56 (2H, d, J = 8.4 Hz). 13C-NMR (100 MHz, CDCl3) d 0.3, 14.2, 22.8, 23.3, 23.3, 23.4, 26.2, 28.9, 29.4, 29.7, 32.0, 65.8, 89.3, 89.3, 92.8, 92.9, 100.1, 203.0, 119.6, 119.7, 120.2, 123.4, 123.6, 124.2, 124.2, 126.5, 126.8, 126.9, 129.0129.1, 129.2, 129.7, 130.7, 130.8, 130.9, 131.4, 132.0, 132.1, 132.2, 136.6, 136.7, 136.8, 138.1, 165.2. (M,P,M)-[3+2]Dialkyne (M,P,M)-6. The title compound (71 mg, 0.049 mmol, 98%) was prepared from (M,P,M)-[3+2]dialkyne bistrimethylsilyl derivative (79 mg, 0.050 mmol) as was (M,P,M)-[3+2]dialkyne. Mp 127128 C (toluene-MeOH). [a]D23  105 (c 0.82, CHCl3). MALDI TOF-MS m/z Calcd for 12C10513CH92O4: 1429.7. Found: 1430.9. UV-VIS (CHCl3) lmax (e) 331 nm (1.2x105). CD (CHCl3, 140 mM) lmax (De) 397 nm (20), 377 ( 68), 326 (64), 295 ( 37), 261 (71). IR (CHCl3) 3304, 1722 cm-1. 1H-NMR (400 MHz, CDCl3) d 0.86 (6H, t, J = 6.9 Hz), 1.20-1.41 (24H, m), 1.43-1.52 (4H, m), 1.86 (4H, quin, J = 7.0 Hz), 1.96 (12H, s), 2.00 (6H, s), 3.57 (2H, s), 4.43 (4H, t, J = 6.8 Hz), 7.47 (2H, d, J = 8.2 Hz), 7.49 (2H, d, J = 8.3 Hz), 7.51 (2H, d, J = 7.9 Hz), 7.67 (2H, dd, J = 8.1, 7.2 Hz), 7.74 (4H, dt, J = 7.1, 5.0 Hz), 8.08 (2H, s), 8.11 (2H, s), 8.15 (2H, s), 8.20 (2H, dd, J = 1.7, 1.5 Hz), 8.36 (2H, dd, J = 1.7, 1.5 Hz), 8.37 (2H, d, J = 1.7, 1.5 Hz), 8.45 (2H, d, J = 8.1 Hz), 8.55 (2H, d, J = 7.7 Hz), 8.56 (2H, d, J = 5.9 Hz). 13C-NMR (100 MHz, CDCl3) d 14.2, 21.6, 22.8, 23.3, 23.4, 26.2, 28.9, 29.4, 29.7, 30.4, 32.0, 65.9, 81.8, 82.4, 89.3, 92.9, 93.0, 119.3, 119.7, 119.7, 123.4, 123.5, 124.2, 125.2, 126.7, 126.7, 126.8, 126.9, 128.1128.9, 129.1, 129.1, 129.2, 129.7, 129.7, 130.3, 130.7, 130.8, 130.9, 130.9, 131.4, 132.0, 132.1, 132.2, 136.7, 136.8, 136.8, 138.1, 165.2. (M,M,M)-[3+3]Cycloalkyne (M,M,M)-3. Under an argon atmosphere, a mixture of tris (dibenzylideneacetone)dipalladium(0)-chloroform adduct (3 mg, 0.003 mmol), cuprous iodide (7 mg, 0.04 mmol), trimesitylphosphine (7 mg, 0.02 mmol), tetrabutylammonium iodide (87 mg, 0.24 mmol), diisopropylethylamine (5 mL) and N,N-dimethylformamide (150 mL) was freeze-evacuated three times in flask A. In flask B, a solution of (M,M,M)-6 (85 mg, 0.059 mmol) and decyl 3,5-diiodebenzoate 7 (30 mg, 0.059 mmol) in toluene (5 mL) was freeze-evacuated three times, and was added dropwise to the flask A over 5 h. The mixture was stirred for another 1 h at room temperature. The reaction was quenched by adding saturated aqueous ammonium chloride, and the organic materials were extracted with chloroform. The organic layer was washed with brine and dried over magnesium sulfate. The solvents were evaporated under a reduced pressure, and separation by recycling GPC gave (M,M,M)-3 (54 mg, 0.032 mmol, 54%). Mp 132-133 C (decomp., toluene-MeOH). [a]D29  403 (c 0.7, CHCl3). MALDI TOF-MS m/z Calcd for 12C12213CH114O6: 1687.7. Found: 1688.3. UV-VIS (CHCl3) lmax (e) 340 nm (2.0x105). CD (CHCl3, 4.0 mM) lmax (De) 380 nm ( 356), 357 ( 448), 334 (450), 262 (132). IR (CHCl3) 3308, 2256, 2210, 1722 cm-1. Anal. (C123H114O6) Calcd for: C, 87.51; H, 6.89%. Found: C, 87.38; H, 6.90%. 1H-NMR (400 MHz, CDCl3, 80 mM) d 0.87 (9H, t, J = 6.6 Hz), 1.26-1.49 (42H, m), 1.92 (6H, quin, J = 7.2 Hz), 1.99 (18H, s), 4.47 (6H, t, J = 6.8 Hz), 7.51 (6H, d, J = 7.3 Hz), 7.74 (6H, dd, J = 7.3, 7.9 Hz), 8.19 (6H, s), 8.25 (3H, t, J = 1.5 Hz), 8.35 (6H, d, J = 1.5 Hz), 8.54 (6H, d, J = 7.9 Hz). 13C-NMR (100 MHz, CDCl3) d 14.3, 22.8, 23.4, 23.4, 26.2, 28.9, 29.5, 29.7, 29.8, 32.0, 65.8, 81.8, 93.0, 119.3, 123.4, 123.5, 124.2, 126.8, 126.9, 129.1, 129.2, 129.7, 129.7, 130.3, 130.9, 131.4, 132.2, 136.8, 138.1, 165.2. (M,P,M)-[3+3]Cycloalkyne (M,P,M)-3. The title compound (65 mg, 0.039 mmol, 50%) was prepared from (M,P,M)-[3+2]dialkyne (110 mg, 0.077 mmol) as was (M,M,M)-3. Mp 136140 C (decomp., toluene-MeOH). [a]D27  301 (c 1.4, CHCl3). UV-VIS (CHCl3) lmax (e) 340 nm (2.2x105). CD (CHCl3, 12 mM) lmax (De) 380 nm ( 191), 357 ( 241), 334 (242), 267 (72). IR (CHCl3) 1725 cm-1. MALDI TOF-MS m/z Calcd for 12C12213CH114O6: 1687.7. Found: 1689.7. Anal. (C123H114O6) Calcd for: C, 87.81; H, 6.89%. Found: C, 87.44; H, 6.91%. 1H-NMR (600 MHz, CDCl3, 98 mM) d 0.87 (9H, t, J = 6.8 Hz), 1.26-1.45 (42H, m), 1.90 (6H, quintet, J = 7.5 Hz), 1.997 (6H, s), 2.002 (12H, s), 4.471 (2H, t, J = 6.9 Hz), 4.474 (4H, t, J = 6.9 Hz), 7.52 (6H, d, J = 6.7 Hz), 7.752 (4H, dd, J = 7.2, 7.5 Hz), 7.758 (2H, dd, J = 7.2, 7.5 Hz), 8.19 (6H, s), 8.262 (2H, t, J = 1.5 Hz), 8.269 (1H, t, J = 1.5 Hz), 8.381 (2H, d, J = 1.5 Hz), 8.388 (4H, d, J = 1.5 Hz), 8.566 (2H, d, J = 1.5 Hz), 8.575 (4H, d, J = 1.5 Hz). 13C-NMR (150 MHz, CDCl3) d 14.2, 22.8, 23.3, 29.4, 29.5, 29.5, 29.7, 29.8, 32.0, 65.51 and 65.55 (1: 2), 88.76 and 88.96 (1: 2), 92.86 and 92.97 (1: 2), 119.7, 119.8, 123.2, 123.4, 123.6, 126.2, 126.3, 128.79 and 128.86 (1: 2), 129.77 and 129.86 (1: 2), 130.62 and 130.71 (2: 1), 131.21 and 131.33 (2: 1), 131.6, 131.7, 131.8, 131.9, 136.4, 165.2 and 165.3 (1: 2).  Figure 4. CD spectra (CHCl3, 25 C) of (M,M,M)-3 at 0.25, 0.64, and 1.53 mM. Inset is the concentration dependencies of De at 330 nm. Figure 5. CD spectra (top) and UV spectra (bottom) of (M,M,M)-3 (4.0 mM, 12 mM) and (M,P,M)-3 (12 mM, 8.5 mM) in chloroform at 25 C. Figure 6.  1/F* of (M,M,M)-3, (M,P,M)-3, and 2 vs stoichiometric concentration at 35 C in chloroform. The molar osmotic coefficient F* is expressed as F* = m/ms where ms is the stoichiometric molarity and m is the osmotic molarity. The numerical value of  1/F* means the average number of association; for example, 1/F* = 1 is for the monomer, 1/F* = 2 for the dimer. The data for 2 are taken from the reference 4. Table 1. 1H-NMR (CDCl3, 22 C) chemical shifts of (M,M,M)-3 at various concentrations.  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