New styryl-substituted tetrapyrazinoporphyrazines [St8PyzPzM] (M = 2NaI, MgII(H2O) and ZnII; St = -CH=CHAr, where Ar = phenyl or cumyl) were prepared by template cyclotetramerization of 5,6-distyrylpyrazine-2,3-dicarbonitriles available from condensation of diaminomaleodinitrile with the substituted cinnamils (StCO) 2 obtained from biacetyl and arylaldehydes ArCHO. The new porphyrazine macrocycles were characterized by electronic absorption and emission spectra, which provide evidence of efficient π-interaction of the peripheral styryl moieties with the central pyrazinoporphyrazine framework. The electronic excitation of the stylbenoid chromophore in the near UV-region (400 nm) leads to strong emission of the porphyrazine chromophore near 700 nm, allowing to consider the styryl-substituted porphyrazines as efficient light-harvesting species. Their spectral properties and electrochemical behavior are compared with those of stylbenoid phthalocyanines and peripherally substituted tetrapyrazinoporphyrazines. © 2010 World Scientific Publishing Company.
Synthesis and properties of styryl-substituted tetrapyrazino-porphyrazines [St(8)PyzPzM], M=2Na(I), Mg-II(H2O) and Zn-II / Donzello, Maria Pia; Viola, Elisa; Tomachinskaya, Larisa A.; Ercolani, Claudio; Corsini, Maddalena; Zanello, Piero; Pavel, A. Stuzhin. - In: JOURNAL OF PORPHYRINS AND PHTHALOCYANINES. - ISSN 1088-4246. - STAMPA. - 14:9(2010), pp. 793-803. [10.1142/s1088424610002677]
Synthesis and properties of styryl-substituted tetrapyrazino-porphyrazines [St(8)PyzPzM], M=2Na(I), Mg-II(H2O) and Zn-II
Donzello, Maria Pia
;Viola, Elisa;
2010
Abstract
New styryl-substituted tetrapyrazinoporphyrazines [St8PyzPzM] (M = 2NaI, MgII(H2O) and ZnII; St = -CH=CHAr, where Ar = phenyl or cumyl) were prepared by template cyclotetramerization of 5,6-distyrylpyrazine-2,3-dicarbonitriles available from condensation of diaminomaleodinitrile with the substituted cinnamils (StCO) 2 obtained from biacetyl and arylaldehydes ArCHO. The new porphyrazine macrocycles were characterized by electronic absorption and emission spectra, which provide evidence of efficient π-interaction of the peripheral styryl moieties with the central pyrazinoporphyrazine framework. The electronic excitation of the stylbenoid chromophore in the near UV-region (400 nm) leads to strong emission of the porphyrazine chromophore near 700 nm, allowing to consider the styryl-substituted porphyrazines as efficient light-harvesting species. Their spectral properties and electrochemical behavior are compared with those of stylbenoid phthalocyanines and peripherally substituted tetrapyrazinoporphyrazines. © 2010 World Scientific Publishing Company.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.