A new approach to the synthesis of porphyrin-fullerene dyads

被引：0
作者：
Stanisław Ostrowski
Agnieszka Mikus
机构：
[1] University of Podlasie,Institute of Chemistry
[2] Polish Academy of Sciences,Institute of Organic Chemistry
来源：
Molecular Diversity | 2003年 / 6卷
关键词：
alkylation; [4+2]-cycloaddition; enyne metathesis; fullerene; porphyrins; vicarious nucleophilic substitution;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A new synthetic approach to porphyrin-fullerene dyads utilizing tetraphenylporphyrin (TPP) and three novel reactions (vicarious nucleophilic substitution, metathesis, and [4+2]-cycloaddition to fullerene) is described. 5-(4-Nitrophenyl)-10,15,20-triphenylporphyrin zinc complex reacts with the carbanion of chloromethyl para-tolyl sulphone (which bears a leaving group Cl at the carbanionic center),affording the nucleophilic substitution of hydrogen product containing a CH2SO2Tol group. The product obtained when alkylated with an alkyl halide (bearing an acetylenic function in the terminal position), followed by the cross-enyne metathesis reaction (with the use of an efficient ruthenium catalyst), resulted in the formation of a TPP-diene building block. Its Diels-Alder reaction with C60-fullerene led to the title dyad – a new artificial photosynthetic model. This method opens up the possibility for synthesis of dyads with variable distances between chromophores, depending on the type of the alkyl halides used.
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页码：315 / 321
页数：6
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共 47 条
  • [1] Fukuzumi S.(1999)60 J. Am. Chem. Soc. 121 3468-3474
  • [2] Nakanishi I.(1997)60 J. Am. Chem. Soc. 119 1400-1405
  • [3] Suenobu T.(1996)Photoinduced charge separation and charge recombination to a triplet state in a carotene-porphyrin-fullerene triad J. Am. Chem. Soc. 118 11771-11782
  • [4] Kadish K. M.(1998)Porphyrin-based photosensitizers for use in photodynamic therapy Tetrahedron 54 4151-4202
  • [5] Liddell P. A.(1978)Photoradiation therapy for the treatment of malignant tumors Cancer Res. 38 2628-2635
  • [6] Kuciauskas D.(2001)Synthesis of covalently linked chlorin-fullerene dyads Bull. Korean Chem. Soc. 22 257-258
  • [7] Sumida J. P.(1986)Synthesis of tetraphenylporphyrins under very mild conditions Tetrahedron Lett. 27 4969-4970
  • [8] Nash B.(1989)Regiospecific aryl nitration of meso-substituted tetraarylporphyrins: A simple route to bifunctional porphyrins J. Org. Chem. 54 2753-2756
  • [9] Nguyen D.(2001)Selective derivatization of TPP on one phenyl ring by nitration and subsequent nucleophilic substitution of hydrogen Bull. Korean Chem. Soc. 22 9-10
  • [10] Moore A. L.(1960)The ionization and coordination behavior of porphyrins Revs. Pure Appl. Chem. 10 35-60
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