Formation of photoactive charge-transfer complexes between methyl viologen and sacrifical electron donors. EDTA and triethanolamine

Hoffman, Morton Z.; Prasad, Dasari R.; Jones, Guilford; Malba, Vincent

doi:10.1021/ja00358a055

Cited by 50 publications

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“…1. The observed red shift of the absorption is typical of the EDA interaction of MV2+ with several anions (4,5). The difference spectrum is shown in the inset in Fig.…”

Section: Association Of Mv'+ With Sds Micellesmentioning

confidence: 82%

“…Equation [5] describes a reaction that occurs within the micelle and not an intermicellar reaction. From eq.…”

Section: Association Of Mv'+ With Sds Micellesmentioning

confidence: 99%

“…From eq. [5], with the assumption that MV2+ is in excess over the amine, where [AIT is the total analytical concentration of the amine and f~ is the corresponding fraction incorporated with the micelles, eq. [3].…”

Section: Association Of Mv'+ With Sds Micellesmentioning

confidence: 99%

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Electron donor–acceptor complexes between naphthylamines and methyl viologen in aqueous sodium dodecyl sulphate solution

Bertolotti¹,

Cosa²,

Gsponer³

et al. 1986

Can. J. Chem.

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The electron donor–acceptor (EDA) interaction between methyl viologen (MV2+) and 1-naphthylamine (1NA), 2-naphthylamine (2NA), and N,N-dimethyl-1-naphthylamine (DMA) was studied in water and in aqueous sodium dodecyl sulphate (SDS). The experimental values of the association constants in water were 8.9, 9.8, and 2.8 M−1 for 1NA, 2NA, and DMA, respectively. In the presence of SDS the observed values were very much higher and strongly dependent upon the detergent concentration. The enhancement in the interaction is due to an increase in the local concentration of the partners in the micellar pseudophase. MV2+ itself was shown to strongly interact with the micelles. A new absorption is present at the red tail of the spectrum of MV2+ in the presence of SDS micelles. An association constant of 1700 M−1 was obtained from this absorption.

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“…1. The observed red shift of the absorption is typical of the EDA interaction of MV2+ with several anions (4,5). The difference spectrum is shown in the inset in Fig.…”

Section: Association Of Mv'+ With Sds Micellesmentioning

confidence: 82%

“…Equation [5] describes a reaction that occurs within the micelle and not an intermicellar reaction. From eq.…”

Section: Association Of Mv'+ With Sds Micellesmentioning

confidence: 99%

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Electron donor–acceptor complexes between naphthylamines and methyl viologen in aqueous sodium dodecyl sulphate solution

Bertolotti¹,

Cosa²,

Gsponer³

et al. 1986

Can. J. Chem.

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“…Hz, 6H);13 CNMR (150 MHz, DMSO-d 6 ): d = 163.17, 162.91, 148.79, 148.13, 146.68, 145.68, 134.18, 131.08, 126.54, 126.18, 125.61, 124.28, 122.63, 56.53, 40.95, 16.33 ppm;e lemental analysis (%) calcd for C 52 H 42 N 6 O 4 Br 4 :C55.05, H3 .73, N7 .41; found:C55.04, H3 .74, N7 .43;M S( MALDI-TOF,D HB matrix): m/z calcd for C 52 H 42 N 6 O 4 :8 14.3246;found 814.3510 [MÀ4Br].Compound 3:Asuspension of PTCDA (500 mg, 1.27 mmol) and N,N-dimethylaminoethylamine (1.5 mL, 13.7 mmol) in DMF (10 mL) was heated at 130 8Cw ith stirring for 5h.A fter cooling to room temperature, THF (25 mL) was added and the resulting precipitate was collected by suction filtration and washed with THF (3 10 mL). 8Cw ith stirring for 12 h. The reaction mixture was then cooled to room temperature and the precipitate was collected by centrifugation.…”

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confidence: 99%

A Viologen–Perylenediimide Conjugate as an Efficient Base Sensor with Solvatochromic Property

et al. 2016

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A viologen-perylenediimide conjugate, denoted PDEV, is prepared for efficient base sensing. The conjugate shows solvatochromic behavior as well. The base sensitivity of viologen is purposefully coupled with the emission property of perylenediimide (PDI) to lower the detection limit. PDEV shows base-sensing ability at the ppb level, which is at least three orders of magnitude lower than those of previously reported sensors. The probe is sensitive toward solvent polarity and generates different shades of colors according to the polarity of the medium (solvent). The photophysical properties show a linear correlation with the solvent polarity, and this makes it an efficient solvatochromic agent. On the other hand, the generation of viologen radical cations by bases affects the aggregation and consequently the absorption and emission behavior of the PDI core. The effect of bases can also be visualized, because the probe generates different colors in the presence of bases, both under normal and under UV light. Organic amines can be detected even in the crystalline state, since the dark red color of the PDEV crystals changes to purple in a reversible fashion on exposure to amine vapors. An easy and practical paper-based tool created by using the probe can efficiently be used to detect solvent polarity and presence of bases optically.

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“…All samples were argon-purged for at least 10 min. The photoreduction chemistry of viologen has been described (17). Data are the result of at least three shots at three or more concentrations.…”

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confidence: 99%

Conformational dependence of electron transfer across de novo designed metalloproteins.

Mutz

McLendon²,

Wishart³

et al. 1996

Proc. Natl. Acad. Sci. U.S.A.

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Flash photolysis and pulse radiolysis measurements demonstrate a conformational dependence of electron transfer rates across a 16-mer helical bundle (three-helix metalloprotein) modified with a capping Co'II(bipyridine)3 electron acceptor at the N terminus and a 1-ethyl-1'-ethyl-4,4'-bipyridinium donor at the C terminus. For the CoIII(peptide)3-1-ethyl-1'-ethyl-4,4'-bipyridinium maquettes, the observed transfer is a first order, intramolecular process, independent of peptide concentration or laser pulse energy. In the presence of 6 M urea, the random coil bundle (0% helicity) has an observed electron transfer rate constant of kobs = 900 ± 100 s-1. In the presence of 25% trifluoroethanol (TFE), the helicity of the peptide is 80% and the k.bs increases to 2000 + 200 s-1. Moreover, the increase in the rate constant in TFE is consistent with the observed decrease in donoracceptor distance in this solvent. Such bifunctional systems provide a class of molecules for testing the effects of conformation on electron transfer in proteins and peptides.De novo design of redox proteins represents a significant challenge for biological and biomimetic chemistry (1, 2). Several maquettes have been designed toward systems in which electrons can be translocated across proteins (3,4). A wealth of data now exist for modified natural proteins like cytochrome c (5, 6). Significant data are also available for modified single peptide systems (7), but conformational equilibria often complicate the interpretation of simple systems (8). Two particularly attractive structural maquettes for the design and study of de novo redox proteins were reported by Ghadhiri et al. (9) and Lieberman and Sasaki (10). Both systems consist of a three helix bundle, whose stoichiometry and topology are defined by the capping metal bipyridyl complex. These bundles have been well characterized in the literature (2, 9-11). Because there are numerous tris-bipyridyl complexes, using this motif to create three helix bundles allows ready access to the many varied spectroscopic, photophysical, and redox properties offered by these metal compounds. Moreover, the ability to control the conformation of these three helix bundles under different solvent conditions provides a facile system in which to study the effects of secondary structure on rates of electron transfer (ET), while maintaining a constant bond connectivity. By probing the ET rates of a designed metalloprotein in both folded and unfolded states, the role of helical secondary structure in mediating ET can be investigated. MATERIALS AND METHODSPeptide Modifications. A minor elaboration on these metalloproteins provides a model bifunctional redox system in which redox active 1-ethyl-1'-ethyl-4,4'-bipyridinium is covalently linked to the C terminus of a bipyridine-modified 16-mer peptide, called "16-mer," and a redox active metal (cobalt) is incorporated into the N terminus as shown in Fig. 1. The sequence of the 16-mer and the structure of the C-terminal modifier, 1-ethyl-i '-ethyl-4,4'-bipyridinium, ...

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Formation of photoactive charge-transfer complexes between methyl viologen and sacrifical electron donors. EDTA and triethanolamine

Abstract: In recent years, model systems have been extensively studied that promote the photoreduction of H 2 0 to H2 through the use 0002-7863/83/ 1505-6360$01

Cited by 50 publications

References 0 publications

Electron donor–acceptor complexes between naphthylamines and methyl viologen in aqueous sodium dodecyl sulphate solution

Electron donor–acceptor complexes between naphthylamines and methyl viologen in aqueous sodium dodecyl sulphate solution

A Viologen–Perylenediimide Conjugate as an Efficient Base Sensor with Solvatochromic Property

Conformational dependence of electron transfer across de novo designed metalloproteins.

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