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Volumn 15, Issue 36, 2009, Pages 9160-9168

Synthesis, characterization, redox properties, and photodynamics of donor-acceptor nanohybrids composed of size-controlled cup-shaped nanocarbons and porphyrins

Author keywords

Donor acceptor systems; Electron transfer; Nanotubes porphyrinoids; Redox chemistry

Indexed keywords

CHARGE-SEPARATED STATE; DONOR-ACCEPTOR SYSTEMS; DONOR-ACCEPTORS; ELECTRON MIGRATION; ELECTRON SPIN RESONANCE MEASUREMENTS; ELECTRON TRANSFER; ELECTRON-ACCEPTOR; ELEMENTAL ANALYSIS; FUNCTIONALIZED; HIGH-PRESSURE MERCURY LAMP; IR SPECTROSCOPY; NANOCARBONS; NANOHYBRIDS; ONE-ELECTRON OXIDATION; PHOTO-IRRADIATION; RADICAL ION PAIRS; REDOX CHEMISTRY; REDOX PROPERTY; RU(BPY); SEMIQUINONE RADICALS; UV/ VIS SPECTROSCOPY; UV/VIS ABSORPTION SPECTRUM;

EID: 70349103832     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900427     Document Type: Article
Times cited : (17)

References (114)
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    • The blurred shadow around a carbon structure is a trace of vapored DMF solvent.
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    • 4): C, 90.57; H, 2.07; N, 1.13; found: C, 90.36; H, 2.06; N, 1.13. This indicates that one porphyrin is attached per 640 carbon atoms.
    • 4): C, 90.57; H, 2.07; N, 1.13; found: C, 90.36; H, 2.06; N, 1.13. This indicates that one porphyrin is attached per 640 carbon atoms.
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    • n was also absorbed a light at 426 nm. Thus, the actual ratio of fluorescence quenching that can be estimated from absorption ratio is about 80%.
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    • The CS lifetime was also determined from the decay time profiles at 750 nm as 0.64 ± 0.01ms.
    • The CS lifetime was also determined from the decay time profiles at 750 nm as 0.64 ± 0.01ms.
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    • n solution was irradiated with a high-pressure mercury lamp (X > 380 nm) equipped with a UV-light cut filter accompanied by rapidly falling temperature.
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    • The transient absorption bands in the NIR region agree with the absorption bands due to TCNQ""; see: V. Ganesan, S.V. Rosokha, J. K. Kochi, J. Am. Chem. Soc. 2003, 125, 2559.
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    • No direct electron transfer from singlet-excited H2P to TCNQ occurs under the present experimental conditions with small concentrations of TCNQ.
    • No direct electron transfer from singlet-excited H2P to TCNQ occurs under the present experimental conditions with small concentrations of TCNQ.
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    • The other substituted TCPP (di- and tetra-substituted TCPP) is also formed as a by-product. After the reaction, tetra-substituted TCPP and trace of di-substituted TCPP were detected by MALDI-TOF mass spectroscopy. These by-products can be easily removed by silica gel column chromatography. The characterization of tri-substituted TCPP also has been carried out by MALDI-TOF mass spectroscopy after the purification. See the Supporting Information (Figure Sl).
    • The other substituted TCPP (di- and tetra-substituted TCPP) is also formed as a by-product. After the reaction, tetra-substituted TCPP and trace of di-substituted TCPP were detected by MALDI-TOF mass spectroscopy. These by-products can be easily removed by silica gel column chromatography. The characterization of tri-substituted TCPP also has been carried out by MALDI-TOF mass spectroscopy after the purification. See the Supporting Information (Figure Sl).
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    • n solution.
    • n solution.
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    • 2P) as the reference compound was prepared as follows: A solution containing tetrakis(4-carboxyphenyl) porphine (50 mg, 63 umol), thionyl chloride (0.20 mL, 2.74 mmol), and pyridine (0.20 mL) in benzene (15.0 mL) was stirred for 2 h under nitrogen atmosphere. The excess pyridine and benzene were removed under reduced pressure. The residue was redissolved in a mixture containing octadecylamine (70.0 mg, 260 umol), pyridine (0.1 mL), and DMF (10.0 mL). The solution was stirred at room temperature for 24 h. The excess amount of pyridine and DMF were removed under reduced pressure. The crude samples were further purified by reprecipitation from chloroform-acetonitrile to obtain tetrakis(Ar-octadecyl-4-aminocarbonylphenyl) porphyrin.
    • 2P) as the reference compound was prepared as follows: A solution containing tetrakis(4-carboxyphenyl) porphine (50 mg, 63 umol), thionyl chloride (0.20 mL, 2.74 mmol), and pyridine (0.20 mL) in benzene (15.0 mL) was stirred for 2 h under nitrogen atmosphere. The excess pyridine and benzene were removed under reduced pressure. The residue was redissolved in a mixture containing octadecylamine (70.0 mg, 260 umol), pyridine (0.1 mL), and DMF (10.0 mL). The solution was stirred at room temperature for 24 h. The excess amount of pyridine and DMF were removed under reduced pressure. The crude samples were further purified by reprecipitation from chloroform-acetonitrile to obtain tetrakis(Ar-octadecyl-4-aminocarbonylphenyl) porphyrin.


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