F. Wessendorf, A. Hirsch / Tetrahedron 64 (2008) 11480–11489
11489
Wasserberg, D.; Wondergem, H. J.; Christianen, P. C. M.; Schenning, A. P. H. J.;
4.13. 5-(E-Ethynyl-phenyl-cyanuric-phenyl)-10,15,20-(3,5-
dimethoxy-phenyl)-porphyrinato zinc II (13)
´
¨
de Leeuw, D. M.; Tomovic, Z.; Wu, J.; Mullen, K.; Maan, J. C. J. Am. Chem. Soc.
2005, 127, 16233–16237; (k) Jonkheijm, P.; Stutzmann, N.; Chen, Z.; de Leeuw,
D. M.; Meijer, E. W.; Schenning, A. P. H. J.; Wu¨rthner, F. J. Am. Chem. Soc. 2006,
128, 9535–9540.
4-Iodophenyl isocyanuric acid (11 mg, 0.032 mmol), Pd2dba3
(1 mg, 0.0006 mmol), AsPh3 (0.2 mmol, 0.0006 mmol) and CuI
(0.5 mg, 0.002 mmol) were dissolved in dry THF (8 mL) and NEt3
(3 mL). Then porphyrin 12 (31 mg, 0.035 mmol) was added and the
reaction mixture was stirred under inert conditions and with ex-
clusion of light for 3 days. After removing the precipitates and
distillation of the solvent the residue was purified by column
chromatography (CH2Cl2/CH2Cl2/EtOAc/THF 2:1:1). Yield: 28 mg
(81%).
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1H NMR (THF-d8, 400 MHz, rt):
d [ppm] 10.69 (br s, 2H, NH), 8.98
(d, 3J¼4.6 Hz, 2H), 8.95 (s, 4H), 8.87 (d, 3J¼4.6 Hz, 2H), 8.25 (d,
3J¼8.1 Hz, 6H), 7.96 (d, 3J¼8.1 Hz, 6H), 7.78 (d, 3J¼8.7 Hz, 2H), 7.38
(s, 6H), 7.07 (d, 3J¼8.6 Hz, 2H), 6.91 (s, 6H), 3.94 (s, 18H). 13C NMR
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(THF-d8, 100.5 MHz, rt):
d [ppm] 159.8 (3C), 150.8 (2C), 150.7 (1C),
150.5 (2C), 150.1 (4C), 149.9 (1C), 146.0 (6C), 144.9 (2C), 138.6 (1C),
135.6 (2C), 132.2 (2C), 131.8 (2C), 131.7 (2C), 130.4 (4C), 130.1 (2C),
124.3 (3C), 123.0 (1C), 121.4 (1C), 120.3 (1C), 114.6 (6C), 100.2 (3C),
94.8 (1C), 90.2 (1C), 55.6 (6C). MS (FAB, NBA): m/z¼1084 [M]þ. UV/
vis (CH2Cl2): lmax (log
3
) [nm]¼43 (5.16), 548 (3.82), 588 (3.10). FTIR
(diamond, rt): [cmꢀ1] 3000, 2970, 2949, 2360, 2342, 1795, 1738,
1721,1590,1548,1515,1488,1489,1421,1366,1351,1229,1216,1204,
1153, 1107, 1062, 1026, 999, 953, 937, 825, 797, 757, 740, 723.
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Acknowledgements
We thank the Deutsche Forschungsgemeinschaft (SFB 583:
Redoxaktive Metallkomplexe – Reaktivita¨tssteuerung durch mole-
kulare Architekturen and Exzellenzcluster EAM-Engineering of
Advanced Materials) for financial support.
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