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1 Electronic Supplementary Information A Novel and Facile Zn-mediated Intramolecular Five-membered Cyclization of β-tetraarylporphyrin Radicals from β-bromotetraarylporphyrins Dong-Mei Shen, Chao Liu, Qing-Yun Chen * Key laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, , China Fax: (internat.) ; Chenqy@mail.sioc.ac.cn Materials and Instrumentations. 1 HNMR spectra were taken either on Varian-360L, or Brucker AM-300 (300MHz) with CDCl 3 as solvent unless otherwise stated. The 1 HNMR chemical shift were reported in parts per million relative to TMS as an internal standard (δ TMS =0). MS and HRMS were recorded on a Hewlett-Packard HP-5989A spectrometer and a Finnigan MAT-8483 mass spectrometer. UV-vis spectra were measured with Varian Cary 100 spectrophotometer. TLC analysis were performed on silica gel plate and column chromatography over silica gel (mesh ), which were both obtained from Qingdao Ocean Chemicals. Unless otherwise noted, reagents were commercial available and used as received. All solvents were purified according to the known procedure. NBS was crystallized from hot water and dried at room temperature in vacuum overnight. Zinc was activated by stirring with 2mol/L HCl solution and kept under N 2. General procedure for preparing the starting material H 2 TAP(Br)(1): A mixture of H 2 TAP (3) (500mg, 1.0equiv) and N-bromosuccinimide (1.1equiv) in dry chloroform (ethanol free, 100mL) was heated under reflux for 30-40min. After being cooled to room temperature, the mixture was evaporated to dryness and the resulting residue was purified by dry column chromatography using petrol ether and dichloromethane as eluent. The red-purple band and dark-purple band were drug out and respectively washed with CH 2 Cl 2. The red-purple band was unconsumed material. 1
2 The dark-purple band was used directly in the next step. An analytical sample was recrystallized from CH 2 Cl 2 /MeOH. (yield 30-40%) H 2 T(p-Me)PP(Br)(1b): UV-vis λ max (CH 2 Cl 2 )/nm: 421, 518, 554, 595, 650. δ H (300MHz, CDCl 3, Me 4 Si) (s, 2H, NH), (m, 12H, p-me), (m, 8H, Ph-H), (m, 2H, Ph-H), (m, 6H, Ph-H), (m, 7H, β-h); MS (MALDI) m/z: (M + +1); HRMS (MALDI) found: C 48 H 38 N 4 Br + requires: H 2 T(p-MeO)PP(Br)(1c): UV-vis λ max (CH 2 Cl 2 )/nm: 425, 522, 558, 596, 653. δ H (300MHz, CDCl 3, Me 4 Si) (s, 2H, NH), 4.10 (s, 12H, p-meo), (m, 8H, Ph-H), (m, 8H, Ph-H), (m, 7H, β-h); MS (MALDI) m/z: (M + +1); HRMS (MALDI) found: C 48 H 38 N 4 O 4 Br + requires: H 2 T(p-Cl)PP(Br)(1d): (Found: C, 61.18; H, 3.01; N, C 44 H 25 N 4 BrCl. 4 2H 2 O requires C, 60.92; H, 3.37; N, 6.46.); UV-vis λ max (CH 2 Cl 2 )/nm: 421, 517, 551, 592, 647; δ H (300MHz, CDCl 3, Me 4 Si) (s, 2H, NH), (m, 8H, Ph-H), 8.01 (d, J = 8.4Hz, 2H, Ph-H), 8.11 (d, J = 5.1, 6H, Ph-H), (m, 7H, β-h); MS (MALDI) m/z: (M + +1). General procedure for zinc insertion into H 2 TAP(Br)(1): A mixture of H 2 TAP(Br)(1) (100mg, 1.0equiv) and Zn(OAc). 2 2H 2 O (5.0equiv) in CH 2 Cl 2 /MeOH (4/1 vol) was heated at reflux for 1h. Then it was washed with water three times. The organic layer was filtered through a silica gel plug (eluting with CH 2 Cl 2 ). The filtrate was evaporated to dryness to yield a reddish purple solid. The compound was sufficiently pure to carry through to the next reaction. An analytical sample was obtained by further flash column chromatography. (yield 95-98%) ZnT(p-Me)(Br)(Zn1b): UV-vis λ max (CH 2 Cl 2 )/nm: 422, 550, 588; δ H (300MHz, CDCl 3, Me 4 Si) 2.72 (s, 12H, p-me), (m, 8H, Ph-H), (m, 2H, Ph-H), 2
3 (m, 6H, Ph-H), (m, 6H, β-h), (m, 1H, β-h); MS (MALDI) m/z: (M + ); HRMS (MALDI) found: C 48 H 35 N 4 BrZn + requires: ZnT(p-MeO)PP(Br)(Zn1c): UV-vis λ max (CH 2 Cl 2 )/nm:425, 552, 590; δ H (300MHz, CDCl 3, Me 4 Si) 4.05 (s, 12H, p-meo), (m, 8H, Ph-H), 7.93 (t, J = 16.5Hz, 3H, Ph-H), (m, 5H, Ph-H), (m, 6H, β-h), (m, 2H, β-h); MS (MALDI) m/z: (M + ); HRMS (MALDI) found: C 48 H 35 N 4 BrZn + requires: ZnT(p-Cl)PP(Br)(Zn1d): (Found: C, 57.78; H, 2.61; N, C 44 H 23 N 4 BrCl 4 Zn. H 2 O requires C, 57.90; H, 2.76; N, 6.14.); UV-vis λ max (CH 2 Cl 2 )/nm: 431, 565, 606; δ H (300MHz, CDCl 3, Me 4 Si) (m, 8H, Ph-H), (m, 8H, Ph-H), (m, 6H, β-h), 9.02 (s, 1H, β-h); MS (MALDI) m/z: (M + ). General procedure for preparing the starting material H 2 TAP(Br) 4 (4): A mixture of H 2 TAP (200mg, 1.0equiv) and N-bromosuccinimide (6.5equiv) in dry chloroform (ethanol free, 40mL) was heated under reflux for 4h. After being cooled to room temperature, the reaction mixture was filtered through a silica gel plug (mesh ; eluting with CH 2 Cl 2 ). The filtrate was evaporated to dryness and the resulting residue was recrystallized from CH 2 Cl 2 /MeOH to give the desired products. (yield 40-65%) H 2 T(p-Me)PP(Br) 4 (4b): (Found: C, 58.15; H, 3.76; N, C 48 H 34 N 4 Br 4 requires C, 58.44; H, 3.47; N, 5.68.); UV-vis λ max (CH 2 Cl 2 )/nm: 438, 536, 612, 683; MS (MALDI) m/z: (M + +1). The title compound was insoluble in common solvents and no 1 H NMR spectrum was obtained. H 2 T(p-MeO)PP(Br) 4 (4c): (Found: C, 52.81; H, 3.41; N, C 48 H 34 N 4 O 4 Br 4. 2H 2 O requires C, 53.06; H, 3.35; N, 5.16.); UV-vis λ max (CH 2 Cl 2 )/nm: 451, 548, 602, 715; δ H 3
4 (300MHz, CDCl 3, Me 4 Si) (s, 2H, NH), 4.11 (s, 12H, P-MeO), (m, 8H, Ph-H), 8.11 (d, J = 8.7Hz, 8H, Ph-H), 8.70 (s, 4H, β-h); MS (MALDI) m/z: (M + +1). (Zn1). General procedure for zinc insertion into H 2 TAP(Br) 4 (4): The procedure was similar to that described above for the preparation of ZnTAP(Br) ZnT(p-Me)PP(Br) 4 (Zn4b): (Found: C, 53.79; H, 3.25; N, C 48 H 32 N 4 Br 4 Zn. H 2 O requires C, 53.99; H, 3.21; N, 5.52.); UV-vis λ max (CH 2 Cl 2 )/nm: 432, 559, 600; δ H (300MHz, DMSO-d 6, Me 4 Si) (s, 12H, P-Me), (m, 8H, Ph-H), (m, 8H, Ph-H), (m, 4H, β-h); MS (MALDI) m/z: (M + ). ZnT(p-MeO)PP(Br) 4 (Zn4c): (Found: C, 51.78; H, 3.31; N, C 48 H 32 N 4 O 4 Br 4 Zn requires C, 51.76; H, 2.70; N, 5.03.); UV-vis λ max (CH 2 Cl 2 )/nm: 436, 562, 606; δ H (300MHz, CDCl 3, Me 4 Si) 4.12 (s, 12H, P-Me), 7.28 (s, 8H, Ph-H), 7.97 (d, J = 8.4Hz, 8H, Ph-H), 8.78 (s, 4H, β-h); MS (MALDI) m/z: (M + ). Procedure for preparing the starting material 11: A mixture of 14 (100mg, 1.0equiv.) (prepared according to the lit. Eur. J. Org. Chem. 2005, 306) and N-bromosuccinimide (3.35equiv.) in dry chloroform (ethanol free) was heated under reflux for 4h. After being cooled to room temperature, the reaction mixture was evaporated to dryness and the resulting residue was purified by flash column chromatography to give the desired product 11 (96mg, 80%). 11: (Found: C, 60.41; H, 2.93; N, C 48 H 26 N 4 F 4 Br. 2 3H 2 O requires C, 60.78; H, 3.40; N, 5.91.); UV-vis λ max (CH 2 Cl 2 )/nm: 451, 549, 631, 698; δ H (300MHz, CDCl 3, Me 4 Si) (m, 12H, Ph-H), (m, 8H, Ph-H), 8.58 (d, J = 5.4Hz, 2H, β-h), 8.66 (d, j = 4.8Hz, 2H, β-h); δ F (282MHz, CDCl 3, CFCl 3 ) (d, J = 19.2Hz, 2F, Por-CF=CF), (d, J = 22.8, 2F, Por-CF); MS (MALDI) m/z: (M + +1). Procedure for zinc insertion into 11: 4
5 (Zn1). The procedure was similar to that described above for the preparation of ZnTAP(Br) Zn11: (Found: C, 57.99; H, 2.64; N, C 48 H 24 N 4 F 4 Br 2 Zn requires C, 58.00; H, 2.84; N, 5.64.); UV-vis λ max (CH 2 Cl 2 )/nm: 382, 486, 642, 704; δ H (300MHz, CDCl 3, Me 4 Si) (m, 12H, Ph-H), (m, 8H, Ph-H), 8.62 (d, J = 4.8Hz, 2H, β-h), 8.69 (d, j = 4.8Hz, 2H, β-h); δ F (282MHz, CDCl 3, CFCl 3 ) (m, 2F, Por-CF=CF), (m, 2F, Por-CF); MS (MALDI) m/z: (M + +1). General procedure for the Zn-mediated intramolecular reactions of β-porphyrin radicals: An oven-dried 50mL Schlenk tube equipped with a magnetic stirring bar was charged with ZnTAP(Br) n (100mg, 1.0equiv), zinc power (50equiv) and freshly distilled DMSO (20mL). The solution was stirred under N 2 for 2-30min. After being cooled to room temperature, CH 2 Cl 2 (20mL) was added and the mixture was filtered. The filtrate was washed with water three times. The organic layer was dried over Na 2 SO 4 and evaporated to dryness. The resulting residue was purified by dry column chromatography using petrol ether and THF as eluent. The red-purple band and yellow-green band were drug out and respectively washed with CH 2 Cl 2. The red-purple band was the hydronated products. The yellow-green band was the desired intramolecular cyclization products. An analytical sample of was obtain by further flash column chromatography. (yield 20-42%) Zn2a: (Found: C, 77.98; H, 4.34; N, C 44 H 26 N 4 Zn requires C, 78.17; H, 3.88; N, 8.29.); UV-vis λ max (CH 2 Cl 2 )/nm: 403, 419, 445 (sh), 466, 505, 591, 679; δ H (300MHz, CDCl 3, Me 4 Si) (m, 2H, Ph-H), (m, 1H, Ph-H), (m, 1H, Ph-H), 7.52 (s, 1H, β-h), (m, 9H, Ph-H), (m, 6H, Ph-H), (m, 6H, β-h); MS (MALDI) m/z: (M + ). Zn2b: (Found: C, 76.14; H, 4.91; N, C 48 H 34 N 4 Zn. 1.5H 2 O requires C, 75.93; H, 4.91; N, 7.38.); UV-vis λ max (CH 2 Cl 2 )/nm: 420, 469, 508, 549, 590; δ H (300MHz, 5
6 CDCl 3, Me 4 Si) (m, 12H, p-me), (m, 10H, 9Ph-H + 1β-H), (m, 3H, Ph-H), (m, 5H, 3Ph-H + 2β-H), 8.97 (s, 4H, β-h); MS (MALDI) m/z: (M + ). Zn2c: (Found: C, 71.91; H, 4.72; N, C 48 H 34 N 4 O 4 Zn. 0.5H 2 O requires C, 71.55; H, 4.44; N, 6.95.); UV-vis λ max (CH 2 Cl 2 )/nm: 423, 473, 511, 552, 591; δ H (300MHz, DMSO-d 6, Me 4 Si) (m, 12H, p-meo), (m, 10H, 9Ph-H + 1β-H), (m, 3H, Ph-H), (m, 5H, 3Ph-H + 2β-H), 8.79 (s, 4H, β-h); MS (MALDI) m/z: (M + ). Zn2d: (Found: C, 63.35; H, 3.27; N, C 44 H 22 N 4 Cl 4 Zn. H 2 O requires C, 63.53; H, 2.91; N, 6.73.); UV-vis λ max (CH 2 Cl 2 )/nm: 420, 446 (sh), 468, 506, 549, 589; δ H (300MHz, CDCl 3, Me 4 Si) (m, 10H, 9Ph-H + 1β-H), (m, 4H, Ph-H), (m, 4H, 2Ph-H + 2β-H), 8.95 (s, 4H, β-h); MS (MALDI) m/z: (M + ). Zn12: (Found: C, 69.17; H, 3.57; N, C 48 H 24 N 4 F 4 Zn. 2H 2 O requires C, 69.11; H, 2.38; N, 6.72.); UV-vis λ max (CH 2 Cl 2 )/nm: 451(sh), 485, 613, 701; δ H (300MHz, CDCl 3, Me 4 Si) (m, 18H, Ph-H + β-h ), (m, 3H, Ph cyclizated -H), (m, 1H, Ph cyclizated -H), 8.21 (d, J = 4.8Hz, 1H, β-h), 8.27 (d, J = 4.8Hz, 1H, β-h); δ F (282MHz, CDCl 3, CFCl 3 ) (m, 2F, Por-CF=CF), (d, 2F, Por-CF); MS (MALDI) m/z: (M + ); HRMS (MALDI) found: C 48 H 25 N 4 F 4 BrZn + requires: Zn13: UV-vis λ max (CH 2 Cl 2 )/nm: 441, 478(sh), 573, 693; δ H (300MHz, CDCl 3, Me 4 Si) (m, 12H, Ph-H), (m, 8H, Ph-H), 8.69 (s, 1H, β-h), 8.78 (d, J = 4.8Hz, 2H, β-h), 8.88 (d, J = 5.7Hz, 2H, β-h); δ F (282MHz, CDCl 3, CFCl 3 ) (d, J = 16.9Hz, 2F, Por-CF=CF), (d, J = 14.7Hz, 2F, Por-CF); MS (MALDI) m/z: (M + ); HRMS (MALDI) found: C 48 H 25 N 4 F 4 BrZn + requires: Demetalation of the mixture of green band: The mixture of green band (100mg) 6
7 was dissolved in CH 2 Cl 2 (50mL). TFA (5mL) was added. The mixture was stirred at room temperature for 2h. Then it was washed with water, saturated NaHCO 3 solution and water. The organic layer was dried over Na 2 SO 4 and evaporated to dryness. The resulting residue was purified by dry column chromatography with petrol ether/ CH 2 Cl 2 (3/1 vol) as eluent. The three band were drug out and respectively washed with CH 2 Cl 2 to yield the products.(8, 45%; 9, 25%; 10, 20%) 8: (Found: C, 74.38; H, 4.39; N, C 44 H 27 N 4 Br. H 2 O requires C, 74.47; H, 4.12; N, 7.90.); UV-vis λ max (CH 2 Cl 2 )/nm: 412, 449, 474, 499(sh), 651; δ H (300MHz, CDCl 3, Me 4 Si) (s, 1H, NH), -0.35(s, 1H, NH), 6.87 (t, 1H, J = 3.8Hz, Ph-H), 7.00 (t, 1H, J = 7.8Hz, Ph-H), (m, 1H, Ph-H), 7.56 (d, 1H, J = 6.6Hz, Ph-H), (m, 9H, Ph-H), (m, 7H, 6Ph-H + 1β-H), (m, 3H,β-H), (m, 1H, β-h), 8.99 (d, 1H, J = 4.2Hz, β-h); MS (MALDI) m/z: (M + +1); HRMS (MALDI) found: C 44 H 28 N 4 Br + requires: : UV-vis λ max (CH 2 Cl 2 )/nm: 422, 452, 475, 603, 648; δ H (300MHz, CDCl 3, Me 4 Si) (s, 1H, NH), (s, 1H, NH), 6.91 (t, 1H, J = 7.8Hz, Ph-H), 7.04 (t, 1H, J = 7.8Hz, Ph-H), 7.48 (d, 1H, J = 6.9Hz, Ph-H), (m, 9H, Ph-H), (m, 7H, Ph-H), (m, 2H, β-h), 8.34 (d, 1H, J = 6.6Hz, β-h), (m, 1H, β-h), (m, 1H, β-h); MS (MALDI) m/z: (M + +1); HRMS (MALDI) found: C 44 H 27 N 4 Br + 2 requires: : UV-vis λ max (CH 2 Cl 2 )/nm: 428, 524, 603, 663; δ H (300MHz, CDCl 3, Me 4 Si) (s, 1H, NH), (s, 1H, NH), (m, 12H, Ph-H), (m, 8H, Ph-H), (m, 5H, β-h); MS (MALDI) m/z: (M + +1); HRMS (MALDI) found: C 44 H 28 N 4 Br + 3 requires:
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