|
|Section2= |Section3= }} Porphyrazines, or tetraazaporphyrins, are tetrapyrrole macrocycles similar to porphyrins and phthalocyanines. Pioneered by Sir R. Patrick Linstead as an extension of his work on phthalocyanines,〔Cook, A. H.; Linstead, R. P., "Phthalocyanines. XI. The preparation of octaphenylporphyrazines from diphenylmaleinitrile." ''J. Chem. Soc.'' 1937, 929-933.(DOI: 10.1039/JR9370000929 )〕 porphyrazines differ from porphyrins in that they contain -meso nitrogen atoms, rather than carbon atoms, and differ from phthalocyanines in that their β-pyrrole positions are open for substitution. These differences confer physical properties that are distinct from both porphyrins and phthalocyanines.〔Ghosh, A.; Fitzgerald, J.; Gassman, P.G.; Almof, J. ''Inorg. Chem.'', 1994, ''33'', 6057-6060. (DOI: 10.1021/ic00104a014 )〕 ==Synthesis== Porphyrazines are prepared by magnesium templated cyclization of maleonitriles.〔Kobayashi, N. Meso-Azaporphyrins and Their Analogues. In ''The Porphyrin Handbook'', Kadish, K.M.; Smith, K.M.; Guilard, R., Eds.; Academic Press; 1999, ''Vol. 2'', pp. 317-321.〕 Cross-cyclization with phthalonitrile or diiminoisoindole derivatives is possible introducing a flexibile synthetic route that has led to the synthesis of porphyrazines with peripheral heterocyclic rings,〔Angeloni, S.; Ercolani, C., New classes of porphyrazine macrocycles with annulated heterocyclic rings. ''Journal of Porphyrins and Phthalocyanines'', 2000, ''4'', 474–483.〕 heteroatom substituents (S, O, N),〔Michel S.L.J.; Hoffman B.M. Baum S.M.; Barrett A.G.M.; "Peripherally functionalized porphyrazines: Novel metallomacrocycles with broad, untapped potential;" Progress in Inorganic Chemistry, 50: 473-590, 2001.〕 peripherally bound metal atoms,〔For example: Zhao, M; Zhong, C.; Stern, C.; Barrett, A.G.M.; Hoffman, B.M., Synthesis and Properties of Dimetallic M1()-M2(Base ) Complexes. ''Inorg. Chem.'', 2004, ''43'', 3377-3385.〕 and mixed -benzo porphyrazine systems.〔Miwa, H., Ishii, K., Kobayashi, N., Electronic Structures of Zinc and Palladium Tetraazaporphyrin Derivatives Controlled by Fused Benzo Rings. ''Chemistry - A European Journal'', 2004,10, 4422–4435.〕 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Porphyrazine」の詳細全文を読む スポンサード リンク
|