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Donzello MP, Ercolani C, Gaberkorn AA, et al. Synthesis, X-ray crystal structure, UV/visible linear and nonlinear (optical limiting) spectral properties of symmetrical and unsymmetrical porphyrazines with annulated 1,2,5-thiadiazole and 1,4-diamyloxybenzene moieties. Chemistry. 2003;9(17):4009-24doi: 10.1002/chem.200304929.
Donzello, M. P., Ercolani, C., Gaberkorn, A. A., Kudrik, E. V., Meneghetti, M., Marcolongo, G., Rizzoli, C., & Stuzhin, P. A. (2003). Synthesis, X-ray crystal structure, UV/visible linear and nonlinear (optical limiting) spectral properties of symmetrical and unsymmetrical porphyrazines with annulated 1,2,5-thiadiazole and 1,4-diamyloxybenzene moieties. Chemistry (Weinheim an der Bergstrasse, Germany), 9(17), 4009-24. https://doi.org/10.1002/chem.200304929
Donzello, Maria Pia, et al. "Synthesis, X-ray crystal structure, UV/visible linear and nonlinear (optical limiting) spectral properties of symmetrical and unsymmetrical porphyrazines with annulated 1,2,5-thiadiazole and 1,4-diamyloxybenzene moieties." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 9,17 (2003): 4009-24. doi: https://doi.org/10.1002/chem.200304929
Donzello MP, Ercolani C, Gaberkorn AA, Kudrik EV, Meneghetti M, Marcolongo G, Rizzoli C, Stuzhin PA. Synthesis, X-ray crystal structure, UV/visible linear and nonlinear (optical limiting) spectral properties of symmetrical and unsymmetrical porphyrazines with annulated 1,2,5-thiadiazole and 1,4-diamyloxybenzene moieties. Chemistry. 2003 Sep 05;9(17):4009-24. doi: 10.1002/chem.200304929. PMID: 12953187.
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Chemistry. 2003 Sep 05;9(17):4009-24. doi: 10.1002/chem.200304929.

Synthesis, X-ray crystal structure, UV/visible linear and nonlinear (optical limiting) spectral properties of symmetrical and unsymmetrical porphyrazines with annulated 1,2,5-thiadiazole and 1,4-diamyloxybenzene moieties.

Chemistry (Weinheim an der Bergstrasse, Germany)

Maria Pia Donzello, Claudio Ercolani, Anna A Gaberkorn, Evgenij V Kudrik, Moreno Meneghetti, Gabriele Marcolongo, Corrado Rizzoli, Pavel A Stuzhin

Affiliations

  1. Dipartimento di Chimica, Università degli Studi di Roma La Sapienza P.le A. Moro 5, 00185 Roma, Italy.

PMID: 12953187 DOI: 10.1002/chem.200304929

Abstract

Co-cyclization of 1,2,5-thiadiazole-3,4-dicarbonitrile and 3,6-diamyloxyphthalodinitrile in the presence of magnesium or lithium amylate in amyl alcohol leads to mixtures containing the Mg derivatives of the symmetrical species tetrakis(1,2,5-thiadiazolo)porphyrazine, (S(4))PzH(2), and tetrakis(1,4-diamyloxybenzo)porphyrazine, (A(4))PzH(2), and the low-symmetry macrocycles bearing peripheral 1,2,5-thiadiazole and 1,4-diamyloxybenzene rings in the ratio 1:3, 2:2 (cis and trans), and 3:1, that is, (SA(3))PzH(2), (S(2)A(2))PzH(2), (SASA)PzH(2), and (S(3)A)PzH(2), respectively. The basic Mg materials were converted to the corresponding free-base macrocycles by treatment with CF(3)COOH. The species were separated from the mixtures by chromatography, either as Mg complexes or demetalated materials. With results on (S(4))PzH(2) and (SA(3))PzH(2) in hand, including crystallographic work on the latter, a general chemical physical investigation has been carried out of all the symmetrical and unsymmetrical free-base macrocycles. The structures of the species (S(2)A(2))PzH(2) and (A(4))PzH(2). were elucidated by single-crystal X-ray crystallography. The effect of the progressive variation of the macrocyclic structure along the series, from the symmetrical (S(4))PzH(2) to its symmetrical partner (A(4))PzH(2) via the low-symmetry 3:1, 2:2 (cis and trans), and 1:3 macrocycles, was studied by IR, (1)H NMR, and UV/Vis linear and nonlinear (optical limiting) measurements. The results are interpreted on the basis of intra- and intermolecular interactions between the electron-deficient 1,2,5-thiadiazole and the electron-donating 1,4-diamyloxybenzene moieties.

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