Metal complexes of 2-aza-2-benzyl-5,10,15,20-tetraphenyl-21-carbaporphyrin: M(2-NCH2C6H5NCTPP) (M=Ni2+, Pd2+) and Mn(2-NCH2C6H5NCTPP)Br (NCTPP=N-confused 5,10,15,20-tetraphenyl porphyrinate)

Hsaio, De-Zhi; Chen, Jyh-Horung; Wang, Shin-Shin; Tung, Jo-Yu

doi:10.1016/j.poly.2011.09.034

Cited by 14 publications

(13 citation statements)

References 13 publications

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“…The abrupt rise in m eff in the range 2 < T <18 K is characteristic of compounds with significant zerofield splitting (ZFS). The room temperature effective moment of 4.26 m B is lower than the spin-only moment (4.9 m B ) for an S = 2 system, but consistent with that (4.34~4.62 μ B ) of other high spin Mn(III) N-confused porphyrins [44][45][46][47].…”

Section: Magnetic Propertiessupporting

confidence: 69%

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The magnetic properties, DNA/HSA binding and nuclease activity of manganese N-confused porphyrin

Peng

Ali

et al. 2016

J. Porphyrins Phthalocyanines

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The first oxidative cleavage of DNA by manganese N-confused porphyrin [chloro(2aza-2-methyl-5,10,15,20-tetrakis(p-chlorophenyl)-21-carbaporphyrin)manganese(III), 1] using H 2 O 2 as oxidant agent and its magnetic, calf thymus DNA(ct-DNA)-and human serum albumin (HSA) binding properties were investigated. The magnitude of the axial (D) zero-field splitting for the mononuclear Mn(III) center in 1 was determined to be approximately 2.71 cm -1 by paramagnetic susceptibility measurements. The DNA-and HSA binding experimental results showed that 1 bound to ct-DNA via an outside groove binding mode and the hydrophobic cavity located in subdomain IIA of HSA with the binding constant of 4.144 × 10 5 M -1 and ~10 6 M -1 , respectively. Thermodynamic parameters revealed that both DNA-and HSA binding were spontaneous process. The main driven forces were the hydrogen bond and van der Waals for the former, but hydrophobic interaction for the latter, which were further confirmed by molecular docking modeling. Manganese N-confused porphyrin 1 could cleave the supercoiled plasmid DNA efficiently in the presence of hydrogen peroxide. Hydroxyl radical ( · OH) was found the active species for oxidative damage of DNA.

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Section: Magnetic Propertiessupporting

confidence: 69%

“…1, gave the value g eff = 1.66, D = 2.71 cm -1 , p = 0.9999 and TIP = 1.87 × 10 -3 (cm 3 .mol -1 ). The |D| value of 1 falls in the range 1 < |D| < 4.9 cm -1 found in related Mn(III) N-confused porphyrins [44][45][46][47].…”

Section: Magnetic Propertiesmentioning

confidence: 73%

The magnetic properties, DNA/HSA binding and nuclease activity of manganese N-confused porphyrin

Peng

Ali

et al. 2016

J. Porphyrins Phthalocyanines

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“…The similar kind of deshielding were found of 15.2-16.1 ppm (or 16.2 ppm) for 13 C and 0.94-1.00 ppm (or 1.1 ppm) for 1 H of the N + vCH(Ar) group in complexes 10, 11 (or complex 7) (Table 4). 16 The bond distance between N(2) and C(3) is 1.319(5) Å [or 1.311( 6) Å] in 5 (or 6), shorter than that of compound 1 [1.334(2) Å] by 0.015 Å (or 0.023 Å), respectively (Table 4). Similar phenomena were observed in the X-ray diffraction data of complexes 10, 11 (or 7).…”

Section: â100%mentioning

confidence: 99%

“…The spectroscopic observations are compared with the results of X-ray diffraction analysis. In addition, we compared this work with the results of our recent report on the crystal structures of Pd(2-NCH 2 C 6 H 5 NCTPP) (10) and Ni(2-NCH 2 C 6 H 5 NCTPP) (11) 16 and with the structures of Ni[2-N(CH 2 ) 8 I NCTPP] (12) 9 and Ni(2-NCH 2 CH 2 BrNCTPP) (13). 17 For the first time, we combine the data from the δ 13 C chemical shifts of C(3) and δ 1 H Scheme 1 Synthesis of 4, 5, 6 and 7.…”

Section: Introductionmentioning

confidence: 99%

A 13C and 1H NMR spectroscopic investigation of the structure of the iminium ion with a dipolar form in metal complexes of 2-N-substituted N-confused porphyrins

et al. 2012

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The crystal structures of chloro(2-aza-2-ethoxycarbonylmethyl-5,10,15,20-tetraphenyl-21-carbaporphyrinato-N,N′N′′) zinc(II) [Zn(2-NCH2COOC2H5NCTPP)Cl; 4], (2-aza-2-ethoxycarbonylmethyl-5,10,15,20-tetraphenyl-21-carbaporphyrinato-N,N′N′′) palladium(II) [Pd(2-NCH2COOC2H5NCTPP); 5], bromo(2-aza-2-ethoxycarbonylmethyl-5,10,15,20-tetraphenyl-21-carbaporphyrinato-N,N′N′′) manganese(III) [Mn(2-NCH2COOC2H5NCTPP)Br; 6], [2-aza-(3′-phenoxypropyl)-5,10,15,20-tetraphenyl-21-carbaporphyrinato-N,N′N′′] nickel(II) [Ni(2-NCH2CH2CH2OC6H5NCTPP); 7] and chloro(2-aza-2-methoxycarbonylmethyl-5,10,15,20-tetraphenyl-21-carbaporphyrinato-N,N′N′′) zinc(II) [Zn(2-NCH2COOCH3NCTPP)Cl; 8] have been established. The g value of 9.54, which was measured from the parallel polarization of the X-band EPR spectra in CHCl3 at 4 K, is consistent with the high spin mononuclear manganese(III) centre (S = 2) in 6. The magnitude of the axial (D) zero-field splitting (ZFS) for the mononuclear Mn(III) centre in 6 was determined approximately to be 1.63 cm(−1) by paramagnetic susceptibility measurements. The NMR spectroscopic investigation of the iminium ion with a dipolar canonical contribution to the metal complexes 5–7, Pd(2-NCH2C6H5NCTPP) (10) and Ni(2-NCH2C6H5NCTPP) (11) in CDCl3 is reported. A resonance between the dipolar canonical form II and covalent canonical form I exists for complexes 5–7, 10 and 11 in CDCl3. To develop the correlations between δ13C [C(3)], δ1H [H(3)] and the canonical form II in 5–7, 10 and 11, this work thoroughly examines the 13C and 1H NMR of N+=CH(Ar) fragment on seven metal complexes of 2-N substituted N-confused porphyrin. According to these results, the 13C [C(3)] and 1H [H(3)] chemical shifts of the N+=CH(Ar) fragment at 20 °C in CDCl3 are separately located at 152.6 ± 0.5 and 8.30 ± 0.15 ppm respectively for the iminium ion. This exists as a dipolar canonical form II for complexes 5–7, 10 and 11, and the N–CH(Ar) group appears at 121.1 ± 0.1 ppm and 6.35 ± 0.01 ppm, which is in a covalent canonical form I contribution to complexes 4 and 8. X-Ray diffraction data indicate that N(2)–C(3) = 1.315 ± 0.011 Å for the dipolar contribution of 5–7, 10–13, while N(2)–C(3) = 1.331 ± 0.008 Å for the covalent contribution of 4 and 8.

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“…However, manganese N-alkyl N-confused porphyrins are relatively more stable and can be easily prepared [11,30]. This phenomenon triggered our interest in the synthesis of manganese N-methyl N-confused porphyrins (3a-3f).…”

Section: Synthesis Of Manganese N-confused Tetraarylporphyrinsmentioning

confidence: 99%

The first manganese N-confused porphyrins catalyzed oxidation of alkene

Peng

Mahmood

Zou

et al. 2014

Journal of Molecular Catalysis A: Chemical

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Metal complexes of 2-aza-2-benzyl-5,10,15,20-tetraphenyl-21-carbaporphyrin: M(2-NCH2C6H5NCTPP) (M=Ni2+, Pd2+) and Mn(2-NCH2C6H5NCTPP)Br (NCTPP=N-confused 5,10,15,20-tetraphenyl porphyrinate)

Cited by 14 publications

References 13 publications

The magnetic properties, DNA/HSA binding and nuclease activity of manganese N-confused porphyrin

The magnetic properties, DNA/HSA binding and nuclease activity of manganese N-confused porphyrin

A 13C and 1H NMR spectroscopic investigation of the structure of the iminium ion with a dipolar form in metal complexes of 2-N-substituted N-confused porphyrins

The first manganese N-confused porphyrins catalyzed oxidation of alkene

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