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Volumn 13, Issue 3, 2007, Pages 891-901

Synthesis, structures, and properties of meso-phosphorylporphyrins: Self-organization through P-oxo-zinc coordination

Author keywords

Cross coupling; P O compounds; Porphyrinoids; Self assembly; X ray diffraction

Indexed keywords

CATALYSIS; PHOSPHORUS; REACTION KINETICS; SELF ASSEMBLY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

EID: 33846485662     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600835     Document Type: Article
Times cited : (71)

References (120)
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    • Quite recently, Arnold and co-workers independently reported the synthesis of meso-phosphorylporphyrins based on the Pd-catalyzed C-P cross-coupling reaction. See: a
    • Quite recently, Arnold and co-workers independently reported the synthesis of meso-phosphorylporphyrins based on the Pd-catalyzed C-P cross-coupling reaction. See: a) F. Atefi, O. B. Locos, M. O. Senge, D. P. Arnold, J. Porphyrins Phthalocyanines, 2006, 10176;
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    • The chemical shifts of the peripheral protons remain almost identical from -10°C to -50°C for 2Zn and from 20°C to -60°C for 3Zn, implying that these compounds exist mostly as dimers in these temperature ranges.
    • The chemical shifts of the peripheral protons remain almost identical from -10°C to -50°C for 2Zn and from 20°C to -60°C for 3Zn, implying that these compounds exist mostly as dimers in these temperature ranges.
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    • It is well known that the meso-phenyl rings of TPP-type porphyrins do not lie in the same plane as the porphyrin ring due to steric repulsion with the neighboring β-protons
    • It is well known that the meso-phenyl rings of TPP-type porphyrins do not lie in the same plane as the porphyrin ring due to steric repulsion with the neighboring β-protons.
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    • X-ray crystal structure data for (2Zn)2: formula C 140H178N8O6P2Zn 2, triclinic, crystal size 0.20×0.10×0.05 mm, space group P1̄, a, 10.5923(14, b, 17.761(2, c, 18.720(2) Å, α, 86.268(8, β, 80.937(8, γ, 74.127(8)°, V, 3344.3(7) Å3, Z, 1, ρcalcd, 1.123 g cm-3, 2θmax, 136.4°, T, 93.1 K, μ, 1.084 mm-1, Tmin, 0.947, Tmax, 0.736, 35256 measured reflections, 11909 independent reflections (Rint, 0.081, 714 refined parameters, wR2, 0.3378, R, 0.1122 [I > 2.00σI, GOF, 1.093, max/min residual electron density 2.21/-0.98 e Å-3. CCDC-281481 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via
    • -3. CCDC-281481 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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    • Zn-O 1.965(10)-1.970(8)Å; P=O 1.486(8)-1.523(12) Å; P-O-Zn 145.0(4)-157.0(7)°: C. A. Kosky, J.-P. Gayda, J. F. Gibson, S. F. Jones, D. J. Williams, Inorg. Chem. 1982, 213173.
    • Zn-O 1.965(10)-1.970(8)Å; P=O 1.486(8)-1.523(12) Å; P-O-Zn 145.0(4)-157.0(7)°: C. A. Kosky, J.-P. Gayda, J. F. Gibson, S. F. Jones, D. J. Williams, Inorg. Chem. 1982, 213173.
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    • Zn-O 1.896(3)-1.910(3) Å; P=O 1.493(3)-1.507(3) Å; P-O-Zn 147.1(2)-170.1(2)°. See ref. [19].
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    • X-ray crystal structure data for 3Zn: formula C74H 81N4OPZn·0.5 H2O, monoclinic, crystal size 0.15 × 0.07 × 0.02 mm, space group P21/n (no. 14, a, 18.9921(4, b, 9.8546(2, c, 36.1694(9) Å, β, 95.8864(8)°, V, 6733.8(3) Å3, Z, 4, ρcalcd, 1.132 g cm-3, 2θmax, 50.0°, T, 103 K, μ, 0.434 mm-1, Tmin, 0.9378, Tmax, 0.9914, 53301 measured reflections, 11856 independent reflections (Rint, 0.1614, 745 refined parameters, wR2, 0.1648, R, 0.0858 [I > 2.00σI, GOF, 1.081, max/min residual electron density 0.581/-0.395 e Å-3. CCDC-609799 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via
    • -3. CCDC-609799 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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    • 3 were unsuccessful.
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    • For discussion about the excitonic coupling of covalently and noncovalently linked porphyrin dimers, see: a R. R. Bucks, S. G. Boxer, J. Am. Chem. Soc. 1982, 104340;
    • For discussion about the excitonic coupling of covalently and noncovalently linked porphyrin dimers, see: a) R. R. Bucks, S. G. Boxer, J. Am. Chem. Soc. 1982, 104340;
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    • -1, were deconvoluted into three Gaussian bands and analyzed.
    • -1, were deconvoluted into three Gaussian bands and analyzed.
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    • -1 at 25°C. H. Imai, S. Nakagawa, E. Kyuno, J. Am. Chem. Soc. 1992, 1146719.
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    • 3 at 25°C. See ref. [3 f].
    • 3 at 25°C. See ref. [3 f].
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    • a values in Equation (1).
    • a values in Equation (1).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.