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23
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For previous examples of porphyrin array synthesis via alkyne coupling reactions, see: Wagner, R. W.; Johnson, T. E.; Lindsey, J. S. J. Am. Chem. Soc. 1996, 118, 11166.
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For examples of multiple alkyne aryl halide and alkene aryl halide coupling reactions, see: Tao, W.; Nesbitt, S.; Heck, R. F. J. Org. Chem. 1996, 55, 63.
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a) The synthesis of the analogous nickel(II) complex of 3 has been previously reported: Arnold, D. P.; Nitschinski, L. J. Tetrahedron 1992, 48, 8781. However, this compound is not suitable for the synthesis of photoactive porphyrin arrays: the central nickel ion cannot be removed or exchanged under mild reaction conditions to obtain other porphyrin chromophores.
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Arnold, D.P.1
Nitschinski, L.J.2
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b) For the synthesis of other alkyne-substituted porphyrin derivatives, see: Arnold, D. P.; Nitschinski, L. J. Tetrahedron Lett. 1993, 34, 693 (meso-ethynyloctaethylporphyrin).
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a) Lindsey, J. S.; Prathapan, S.; Johnson, T. E.; Wagner, R. W. Tetrahedron 1994, 50, 8941.
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For the analogous Wittig reaction of 2-formyl nickel tetraphenylporphyrin, see: Callot, H. J. Bull. Soc. Chim. Fr. 1973, 3413.
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Callot, H.J.1
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36
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34548004764
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note
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The same is observed with 1: the zinc complex shows an NMR spectra of poor resolution, whereas 1 gives well resolved NMR spectra.
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37
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85082849241
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1,3,5-Triiodobenzene was prepared from commercially available 1,3,5-tribromobenzene according to Suzuki, H.; Kondo, A.; Inouye, M.; Ogawa, T. Synthesis 1986, 121.
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Suzuki, H.1
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Ogawa, T.4
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38
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0000349749
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For the demetalation of copper porphyrins more vigorous conditions are necessary: Smith, K. M.; Graig, G. W. J. Org. Chem. 1983, 48, 4302.
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Smith, K.M.1
Graig, G.W.2
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