On the ionization potential of chlorophyll and bacteriochlorophyll in aqueous environment

Bernas, A.; Grand, D.; Hautecloque, S.; Myasoedova, Tatiana N.

doi:10.1016/0009-2614(84)85314-2

Cited by 8 publications

(3 citation statements)

References 18 publications

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“…This reaction is favored thermodynamically if the IE of the analyte is lower than the IE of the matrix. The IE of chlorophyll (a) has been determined to be in the range of 4.5–6.2 eV . When considering the higher IE of 9,10 ‐DPA (7.04 eV), electron transfer from chlorophyll (a) to ( 9,10 ‐DPA +. )…”

Section: Resultsmentioning

confidence: 99%

“…Conventional MALDI matrices a-CHCA 189 8.5 [13] n/a n/a sinapinic acid 224 7.7 [13] n/a n/a 2,5-DHB 154 8.1 [22] n/a n/a dithranol 226 6.9 [13] n/a n/a 9,10-Diphenylanthracene as a matrix for MALDI-MS has been determined to be in the range of 4.5-6.2 eV. [32][33][34] When considering the higher IE of 9,10-DPA (7.04 eV), [19] electron transfer from chlorophyll (a) to (9,10-DPA +. ) is thus exothermic.…”

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confidence: 99%

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9,10‐Diphenylanthracene as a matrix for MALDI‐MS electron transfer secondary reactions

Boutaghou

Cole

2012

J. Mass. Spectrom.

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The most common secondary-ionization mechanism in positive ion matrix-assisted laser desorption/ionization (MALDI) involves a proton transfer reaction to ionize the analyte. Peptides and proteins are molecules that have basic (and acidic) sites that make them susceptible to proton transfer. However, non-polar, aprotic compounds that lack basic sites are more difficult to protonate, and creating charged forms of this type of analyte can pose a problem when conventional MALDI matrices are employed. In this case, forming a radical molecular ion through electron transfer is a viable alternative, and certain matrices may facilitate the process. In this work, we investigate the performance of a newly developed electron-transfer secondary reaction matrix: 9,10-diphenylanthracene (9,10-DPA). The use of 9,10-DPA as matrix for MALDI analysis has been tested using several model compounds. It appears to promote ionization through electron transfer in a highly efficient manner as compared to other potential matrices. Thermodynamic aspects of the observed electron transfers in secondary-ionization reactions were also considered, as was the possibility for kinetically controlled/endothermic, electron-transfer reactions in the MALDI plume.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

9,10‐Diphenylanthracene as a matrix for MALDI‐MS electron transfer secondary reactions

Boutaghou

Cole

2012

J. Mass. Spectrom.

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“…Most of the available experimental information on the electronic properties of chlorophylls is determined in solution. This feature fostered theoretical studies on the electronic properties of photosynthetic chromophores in solution, [3][4][5][6][7][8][9][10] or in interaction with hydrogen bonding species, [10][11][12][13][14][15][16][17][18] or with the protein environment. 19,20 Some specific aspects for understanding electronic properties of solvated chromophores are of general interest and include, for example, the dependence of these properties on hydrogen bonding, and the influence of long-range solutesolvent interactions on the absorption spectra.…”

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confidence: 99%

Born-Oppenheimer molecular dynamics and electronic properties of chlorophyll-c2 in liquid methanol

Cabral

Coutinho

Canuto

2013

The Journal of Chemical Physics

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First principles Born-Oppenheimer molecular dynamics of chlorophyll-c2 (chlc2) in liquid methanol is reported. The structure of the chromophore-methanol solution is characterized by non-symmetric solvation and by the displacement of a pentacoordinated Mg atom from the π macrocycle plane of chlc2. Non-symmetrical solvation is in keeping with experimental data reported for chlorophyll-a and bacteriochlorophyll-a indicating a preferential side of the π macrocycle for binding a fifth ligand. The average displacement of the Mg atom (0.38 Å) is similar to X-ray data on magnesium phthalocyanine (~0.45 Å) and ethyl chlorophyllide-a dihydrate crystals (0.39 Å). The displacement of Mg from the macrocycle plane influences the orientational order of the methanol molecules in the axial region and the results indicate that the face defined by the methoxycarbonyl moiety exhibits a solvatophobic behavior. The maximum of the Soret (B) band for chlc2 in liquid methanol (464 nm) is in good agreement with the experimental value (451 nm) and it is also very close to a recent result for chlc2 in liquid 2-methyl tetrahydrofuran (466 nm). Intramolecular hydrogen bonding involving the carboxyl and methoxycarbonyl moieties of chlc2 leads to a blueshift of ~20 nm of the B band maximum.

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Photoinduced electron transfer in arranged media

Fox

1991

Topics in Current Chemistry

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-Photoinduced electron transfer can be achieved in absorptive polymeric coatings and in self-organizing liquid crystalline porphyrins. The efficiency of sensitized photocurrent generation by pendent 10-substituted anthrylethyl derivatives of methacrylate can be related to the photophysical properties of monomeric and dimeric model compounds and to the proximity of approach of nearest-neighbor chromophores. of a thin film of liquid crystalline porphyrin sandwiched between indium tin oxide electrodes results in induced asymmetry in the cell and to efficient photocurrent production.

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On the ionization potential of chlorophyll and bacteriochlorophyll in aqueous environment

Cited by 8 publications

References 18 publications

9,10‐Diphenylanthracene as a matrix for MALDI‐MS electron transfer secondary reactions

9,10‐Diphenylanthracene as a matrix for MALDI‐MS electron transfer secondary reactions

Born-Oppenheimer molecular dynamics and electronic properties of chlorophyll-c2 in liquid methanol

Photoinduced electron transfer in arranged media

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