Photophysics and Photochemistry of 22π and 26π Acetylene-Cumulene Porphyrinoids

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The aromatic 26π acetylene-cumulene porphyrinoid 8 has been synthesized by a reaction sequence involving reductive carbonyl coupling of the dialdehyde 12 utilizing low-valent titanium in the crucial step. Like its lower 22π homologs 6 and 7, the new tetrapyrrolic macrocycle 8 is centrosymmetric in t...

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Autor principal: Mãrtire, D.O
Otros Autores: Jux, N., Aramendía, P.F, Martín Negri, R., Lex, J., Braslavsky, Silvia Elsa, Schaffner, K., Vogel, E.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1992
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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100 1 |a Mãrtire, D.O. 
245 1 0 |a Photophysics and Photochemistry of 22π and 26π Acetylene-Cumulene Porphyrinoids 
260 |c 1992 
270 1 0 |m Schaffner, K.; Max-Planck-Institut für Strahlenchemie, D-4330 Mülheim an der Ruhr, Germany 
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506 |2 openaire  |e Política editorial 
520 3 |a The aromatic 26π acetylene-cumulene porphyrinoid 8 has been synthesized by a reaction sequence involving reductive carbonyl coupling of the dialdehyde 12 utilizing low-valent titanium in the crucial step. Like its lower 22π homologs 6 and 7, the new tetrapyrrolic macrocycle 8 is centrosymmetric in the crystal and has a practically planar ring framework. The photophysical and photochemical properties of 6-8 have been studied and compared to those of the related 8π porphycene 5. The absorption spectrum of 8 has the most red-shifted and intensified visible bands (εmax = 119600 at 889 nm in dichloromethane) of this particular series of (4 + 2)π porphyrinoids. None of the compounds exhibit any photoreactivity. The photophysical properties were determined by a combination of techniques, including steady-state thermal lensing, flash photolysis, laser-induced optoacoustic spectroscopy (LIOAS), and steady-state and time-resolved NIR spectroscopy. The 22π and 26π porphyrinoids do not phosphoresce. The triplet energy (ET) of 7 was therefore measured by way of reversible energy transfer to oxygen yielding singlet molecular oxygen, O2(1Δg), indirect detection by LIOAS of the increase in triplet yield induced by O2(3Σg-)-enhanced S ⟶T intersystem crossing afforded the ET of 6, and an upper limit of ET could be obtained by energy-transfer experiments from O2(1Δg) to 8. The quantum yields of fluorescence, triplet formation, and the ET values dropped significantly on going from 5 to 6-8 (all measurements at room temperature). The triplet energies of 6, 7, and 8 are all below the energy of O2(1Δg). Compound 7, with the highest ET of the three, produces O2(1Δg) with a quantum yield of ΦΔ= 0.06 through a reversible energy-transfer mechanism. Although this value is about six times smaller than ΦΔ of 5, the phototherapeutic activities of both 5 and 7 toward tumors in mice are comparable. The ΦΔ values for 6 and 8 are lower than 10-3; hence, these porphyrinoids do not function as photodynamic sensitizers. © 1992, American Chemical Society. All rights reserved.  |l eng 
593 |a Max-Planck-Institut für Strahlenchemie, D-4330 Mülheim an der Ruhr, Germany 
593 |a Max-Planck-Institut für Strahlenchemie Institut für Organische Chemie, Universitat Köln, D-5000 Köln 41, Germany 
593 |a Facultad de Ciencias Exactas y Naturales, Departamento de Quimica Inorgénica, Analitica y Quimica Fisica, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina 
700 1 |a Jux, N. 
700 1 |a Aramendía, P.F. 
700 1 |a Martín Negri, R. 
700 1 |a Lex, J. 
700 1 |a Braslavsky, Silvia Elsa 
700 1 |a Schaffner, K. 
700 1 |a Vogel, E. 
773 0 |d 1992  |g v. 114  |h pp. 9969-9978  |k n. 25  |p J. Am. Chem. Soc.  |x 00027863  |w (AR-BaUEN)CENRE-19  |t Journal of the American Chemical Society 
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856 4 0 |u https://doi.org/10.1021/ja00051a032  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00027863_v114_n25_p9969_Martire  |y Handle 
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