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, 10-3 mol) was dissolved in 5 mL of MeOH and NaOMe (60 mg, 1.1 ´ 10-3 mol) was added. The mixture was stirred at room temperature for 30 minutes and then treated with Dowex 50WX4 (H + ) (2 g), filtered and evaporated to give Man-SH (277 mg, 93 %)
, Synthesis of 12-Ni mixture was achivied following the synthetic procedure reported in ref, vol.110
,
, MHz, CDCl3, 298 K): d 8.67 (d, 1H, Hpyrr, 3 JH-H = 5.0 Hz), 8.54 (d, 1H, Hpyrr, 3 JH-H = 5.0 Hz), vol.8
,
,
, CH2Cl2): lmax (log ?), vol.343
, trans 13-Ni: 1 H NMR (400Mz, CDCl3, 298 K): d 8.63 (d, 1H, Hpyrr, 3 JH-H = 5.0 Hz), 8.60 (d, 1H, Hpyrr, 3 JH-H = 5.0 Hz), vol.8
, , vol.3
,
, CH2Cl2): ?max (log ?) 446 (5.3), vol.564, p.611
,
Several attemps failed to prepare cis [Zn(AuCl)2] using procedure A Procedure B. A solution of the porphyrin trans Zn-BF4 (20 mg, 1.5 ´ 10-5 mol, 1 eq.) and ,
, mL/10 drops) was added dropwise. The reaction mixture was stirred at room temperature for 1 hour and monitored by silica gel TLC analysis. When the reaction was completed, the solvent was evaporated and the crude product was purified by column chromatography (SiO2, eluent CHCl3). Crystallization from CHCl3/n-hexane afforded cis, a THF/MeOH mixture
,
,
3 JH-H = 8.3 Hz), 3.14 (s, 6H, HNMe), 2.90 (s, 6H, HNMe), vol.1 ,
, C{ 1 H} NMR (125.7 MHz, CDCl3, vol.398
, CHCl3): lmax (log e) = 449 (5.4), vol.580
,
DMSO-d6, 298 K): 2.11´1011´11´10-10 m 2 s-1. Synthesis of 17-Zn A ,
, ) of the later solution were added to a Schlenk tube containing porphyrin [ZnAuCl] (30 mg, 2.5 ´ 10-5 mol, 1 eq.). After a final addition of a 0.25 M KOH solution in MeOH (300 µL, 7.5 ´ 10-5 mol, 3 eq.), the reaction mixture was stirred at room temperature. After 72 hours, a dark purple precipitate appeared. After filtration, the solid was redispersed in fresh MeOH (10 mL) and submitted to ultrasounds for 10 minutes
, 400 MHz, CD2Cl2, 298 K): d 8.96 (d, 6H, Hpyrr, 3 JH-H = 5 Hz), 8.95 (s, 6H, Hpyrr), 8.90 (d, 6H, Hpyrr, 3 JH-H = 5 Hz), vol.8
, 7.82 (s, 3H, HPh), vol.7
, 7.65 (d, 6H, HPh, 3 JH-H = 8.3 Hz), vol.7
, C{ 1 H} NMR (125.7 MHz, CD2Cl2): d 199.4 (NHC), vol.152
,
, m/z calcd for C219H207Au3N18Zn3 :3878.2307
400 MHz, CD2Cl2, 298 K): 2.80´1080´80´10-10 m 2 s-1. Synthesis of trans ,
, After the addition of a 0.25 M KOH solution in MeOH (800 µL, 20.0 ´ 10-5 , 10 equiv), the reaction mixture was stirred at room temperature. After 24 hours, the solvent was evaporated. Crystallization from CH2Cl2/MeOH afforded trans, A solution of phenylacetylene (4.9 ´ 10-3 M) was prepared in THF. Then, 10.2 mL (5.0
, 400 MHz, CD2Cl2, 298 K): d 8.56 (s, 4H, Hpyrr), 8.14 (d, 8H, HAr meso, 3 JH-H = 8.3 Hz), 7.86 (d, 8H, HAr meso, 3 JH-H = 8.3 Hz), 7.33 (m, 4H, HPh)
, C{ 1 H} NMR (125.7 MHz, CD2Cl2, 298 K): d 198.4 (NHC)
, CH2Cl2): lmax (log e) = 435 (5.5), vol.544
, MS (MALDI-TOF + ): m/z calcd for C82H80Au2N8Ni : 1628.5 [M] ·+
Synthesis of cis, n = 2115 cm-1 (C?C) ,
, After the addition of a 0.25 M KOH solution in MeOH (800 µL, 20.0 ´ 10-5 , 10 eq.), the reaction mixture was stirred at room temperature. After 24 hours, the solvent was evaporated. Crystallization from CH2Cl2/MeOH afforded cis, A solution of phenylacetylene (4.9 ´ 10-3 M) was prepared in THF. Then, 10.2 mL (5.0
,
,
, JH-H = 8.3 Hz), 7.32 (m, 4H, HPh), 7.26-7.10 (m, 6H, HPh), 3.13 (s, 6H, HNMe)
, CH2Cl2): lmax (log e) = 434 (5.5), vol.543
, MS (MALDI-TOF + ) : m/z calcd for C82H80Au2N8Ni : 1628.5 [M] ·+
Synthesis of 18-Ni A solution of 1,3,5-tris(4-ethynylphenyl)benzene (1.8 ´ 10-3 M) was prepared in THF. Then, n = 2114 cm-1 (C?C), vol.7 ,
, After the addition of a 0.25 M KOH solution in MeOH (800 µL, 2.0 ´ 10-4 mol, 15 eq.), the reaction mixture was stirred for 6 hours at 50°C and a. a red precipitate appeared. The title compound was isolated by vacuum filtration
Anal. calc (%) for (C129H117Au3N12Ni1.5)n : C 61, vol.64 ,
, IR (ATR): n = 2100 cm-1 (C?C)