Proton-controlled Action of an Imidazole as Electron Relay in a Photoredox Triad.
Artificial Photosynthesis
Electron Relay
Molecular Triad
Photoinduced Electron Transfer
Proton Transfer
Journal
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology
ISSN: 1474-9092
Titre abrégé: Photochem Photobiol Sci
Pays: England
ID NLM: 101124451
Informations de publication
Date de publication:
Feb 2022
Feb 2022
Historique:
received:
09
08
2021
accepted:
18
12
2021
pubmed:
7
1
2022
medline:
25
2
2022
entrez:
6
1
2022
Statut:
ppublish
Résumé
Electron relays play a crucial role for efficient light-induced activation by a photo-redox moiety of catalysts for multi-electronic transformations. Their insertion between the two units reduces detrimental energy transfer quenching while establishing at the same time unidirectional electron flow. This rectifying function allows charge accumulation necessary for catalysis. Mapping these events in photophysical studies is an important step towards the development of efficient molecular photocatalysts. Three modular complexes comprised of a Ru-chromophore, an imidazole electron relay function, and a terpyridine unit as coordination site for a metal ion were synthesized and the light-induced electron transfer events studied by laser flash photolysis. In all cases, formation of an imidazole radical by internal electron transfer to the oxidized chromophore was observed. The effect of added base evidenced that the reaction sequence depends strongly on the possibility for deprotonation of the imidazole function in a proton-coupled electron transfer process. In the complex with Mn
Identifiants
pubmed: 34988933
doi: 10.1007/s43630-021-00163-2
pii: 10.1007/s43630-021-00163-2
doi:
Substances chimiques
Imidazoles
0
Protons
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
247-259Subventions
Organisme : French Infrastructure for Integrated Structural Biology
ID : ANR-10-INSB-05-01
Organisme : Domaine d'Intérêt Majeur Logiciels et Systèmes Complexes
ID : SurPhox-NC
Informations de copyright
© 2022. The Author(s), under exclusive licence to European Photochemistry Association, European Society for Photobiology.
Références
Ibrahim, M., Fransson, T., Chatterjee, R., Cheah, M. H., Hussein, R., Lassalle, L., et al. (2020). Untangling the sequence of events during the S2 –> S3 transition in photosystem II and implications for the water oxidation mechanism. Proceedings of the National Academy of Sciences of the United States of America, 117(23), 12624–12635. https://doi.org/10.1073/pnas.2000529117
doi: 10.1073/pnas.2000529117
pubmed: 32434915
pmcid: 7293653
Lubitz, W., Chrysina, M., & Cox, N. (2019). Water oxidation in photosystem II. Photosynthesis Research, 142(1), 105–125. https://doi.org/10.1007/s11120-019-00648-3
doi: 10.1007/s11120-019-00648-3
pubmed: 31187340
pmcid: 6763417
Styring, S., Sjoholm, J., & Mamedov, F. (2012). Two tyrosines that changed the world: Interfacing the oxidizing power of photochemistry to water splitting in photosystem II. Biochimica et Biophysica Acta, 1817(1), 76–87. https://doi.org/10.1016/j.bbabio.2011.03.016
doi: 10.1016/j.bbabio.2011.03.016
pubmed: 21557928
Brettel K, Schlodder E, Witt HT (1984) Nanosecond reduction kinetics of photooxidized chlorophyll-aII (P-680) in single flashes as a probe for the electron pathway, H+-release and charge accumulation in the O2-evolving complex. Biochimica et Biophysica Acta (BBA) Bioenergetics, 766(2):403–415 https://doi.org/10.1016/0005-2728(84)90256-1
Hammarstrom, L., & Styring, S. (2011). Proton-coupled electron transfer of tyrosines in Photosystem II and model systems for artificial photosynthesis: the role of a redox-active link between catalyst and photosensitizer. Energy & Environmental Science, 4(7), 2379–2388. https://doi.org/10.1039/c1ee01348c
doi: 10.1039/c1ee01348c
Zhao, Y. X., Swierk, J. R., Megiatto, J. D., Sherman, B., Youngblood, W. J., Qin, D. D., et al. (2012). Improving the efficiency of water splitting in dye-sensitized solar cells by using a biomimetic electron transfer mediator. Proceedings of the National Academy of Sciences of the United States of America, 109(39), 15612–15616
doi: 10.1073/pnas.1118339109
Lachaud, T., Quaranta, A., Pellegrin, Y., Dorlet, P., Charlot, M. F., Un, S., et al. (2005). A biomimetic model of the electron transfer between P-680 and the TyrZ-His190 pair of PSII. Angewandte Chemie-International Edition, 44(10), 1536–1540. https://doi.org/10.1002/anie.200461948
doi: 10.1002/anie.200461948
pubmed: 15678434
Moore, G. F., Hambourger, M., Kodis, G., Michl, W., Gust, D., Moore, T. A., et al. (2010). Effects of protonation state on a tyrosine-histidine bioinspired redox mediator. The Journal of Physical Chemistry B, 114(45), 14450–14457. https://doi.org/10.1021/jp101592m
doi: 10.1021/jp101592m
pubmed: 20476732
Megiatto, J. D., Jr., Mendez-Hernandez, D. D., Tejeda-Ferrari, M. E., Teillout, A. L., Llansola-Portoles, M. J., Kodis, G., et al. (2014). A bioinspired redox relay that mimics radical interactions of the Tyr-His pairs of photosystem II. Nature Chemistry, 6(5), 423–428. https://doi.org/10.1038/nchem.1862
doi: 10.1038/nchem.1862
pubmed: 24755594
Manbeck, G. F., Fujita, E., & Concepcion, J. J. (2016). Proton-coupled electron transfer in a strongly coupled photosystem II-inspired chromophore-imidazole-phenol complex: Stepwise oxidation and concerted reduction. Journal of the American Chemical Society, 138(36), 11536–11549. https://doi.org/10.1021/jacs.6b03506
doi: 10.1021/jacs.6b03506
pubmed: 27538049
Chen, J., Kuss-Petermann, M., & Wenger, O. S. (2015). Dependence of reaction rates for bidirectional PCET on the electron donor-electron acceptor distance in phenol-Ru(2,2’-bipyridine)(3)(2)(+) dyads. The Journal of Physical Chemistry B, 119(6), 2263–2273. https://doi.org/10.1021/jp506087t
doi: 10.1021/jp506087t
pubmed: 25078952
Chararalambidis, G., Das, S., Trapali, A., Quaranta, A., Orio, M., Halime, Z., et al. (2018). Water molecules gating a photoinduced one-electron two-protons transfer in a tyrosine/histidine (Tyr/His) model of photosystem II. Angewandte Chemie (International ed. in English), 57(29), 9013–9017. https://doi.org/10.1002/anie.201804498
doi: 10.1002/anie.201804498
Herrero, C., Quaranta, A., Leibl, W., Rutherford, A. W., & Aukauloo, A. (2011). Artificial photosynthetic systems. Using light and water to provide electrons and protons for the synthesis of a fuel. Energy & Environmental Science, 4(7), 2353–2365. https://doi.org/10.1039/c0ee00645a
doi: 10.1039/c0ee00645a
Quaranta, A., Lachaud, F., Herrero, C., Guillot, R., Charlot, M. F., Leibl, W., et al. (2007). Influence of the protonic state of an imidazole-containing ligand on the electrochemical and photophysical properties of a Ruthenium(II)Polypyridine-type complex. Chemistry-a European Journal, 13(29), 8201–8211. https://doi.org/10.1002/chem.200700185
doi: 10.1002/chem.200700185
Limburg, J., Vrettos, J. S., Chen, H., de Paula, J. C., Crabtree, R. H., & Brudvig, G. W. (2001). Characterization of the O(2)-evolving reaction catalyzed by [(terpy)(H2O)Mn(III)(O)2Mn(IV)(OH2)(terpy)](NO3)3 (terpy = 2,2’:6,2"-terpyridine). Journal of the American Chemical Society, 123(3), 423–430. https://doi.org/10.1021/ja001090a
doi: 10.1021/ja001090a
pubmed: 11456544
Chen, H., Tagore, R., Das, S., Incarvito, C., Faller, J. W., Crabtree, R. H., et al. (2005). General synthesis of di-mu-oxo dimanganese complexes as functional models for the oxygen evolving complex of photosystem II. Inorganic Chemistry, 44(21), 7661–7670. https://doi.org/10.1021/ic0509940
doi: 10.1021/ic0509940
pubmed: 16212393
Herrero, C., Quaranta, A., Protti, S., Leibl, W., Rutherford, A. W., Fallahpour, R., et al. (2011). Light-Driven Activation of the [H(2)O(terpy)Mn(III)-mu-(O(2))-Mn(IV)(terpy)OH(2)] Unit in a Chromophore-Catalyst Complex. Chemistry-an Asian Journal, 6(6), 1335–1339. https://doi.org/10.1002/asia.201100030
doi: 10.1002/asia.201100030
Tebo, A. G., Das, S., Farran, R., Herrero, C., Quaranta, A., Fallahpour, R., et al. (2017). Light-driven electron transfer in a modular assembly of a ruthenium(II) polypyridine sensitiser and a manganese(II) terpyridine unit separated by a redox active linkage. DFT analysis. Comptes Rendus Chimie, 20(3), 323–332. https://doi.org/10.1016/j.crci.2016.08.010
doi: 10.1016/j.crci.2016.08.010
Herrero, C., Quaranta, A., Fallahpour, R. A., Leibl, W., & Aukauloo, A. (2013). Identification of the Different Mechanisms of Activation of a [Ru-II(tpy)(bpy)(OH2)](2+) Catalyst by Modified Ruthenium Sensitizers in Supramolecular Complexes. Journal of Physical Chemistry C, 117(19), 9605–9612. https://doi.org/10.1021/Jp4025816
doi: 10.1021/Jp4025816
Watanabe, T., & Honda, K. (1982). Measurement of the extinction coefficient of the methyl viologen cation radical and the efficiency of its formation by semiconductor photocatalysis. The Journal of Physical Chemistry, 86(14), 2617–2619. https://doi.org/10.1021/j100211a014
doi: 10.1021/j100211a014
Qin, X. Z., Liu, A., Trifunac, A. D., & Krongauz, V. V. (1991). Photodissociation of hexaarylbiimidazole. 1. Triplet-state formation. The Journal of Physical Chemistry, 95(15), 5822–5826. https://doi.org/10.1021/j100168a022
doi: 10.1021/j100168a022
Sathe, S. S., Ahn, D., & Scott, T. F. (2015). Re-examining the photomediated dissociation and recombination kinetics of hexaarylbiimidazoles. Industrial & Engineering Chemistry Research, 54(16), 4203–4212. https://doi.org/10.1021/ie504230c
doi: 10.1021/ie504230c
Coraor, G. R., Riem, R. H., MacLachlan, A., & Urban, E. J. (1971). Flash photolysis of a substituted hexaarylbiimidazole and reactions of the imidazolyl radical. The Journal of Organic Chemistry, 36(16), 2272–2275. https://doi.org/10.1021/jo00815a016
doi: 10.1021/jo00815a016
Eigen, M. (1964). Proton transfer, acid-base catalysis, and enzymatic hydrolysis. Part I: ELEMENTARY PROCESSES. Angewandte Chemie International Edition in English, 3(1), 1–19. https://doi.org/10.1002/anie.196400011
doi: 10.1002/anie.196400011
Nurminen, E. J., Mattinen, J. K., & Lönnberg, H. (2001). Nucleophilic and acid catalysis in phosphoramidite alcoholysis. Journal of the Chemical Society, Perkin Transactions, 2(11), 2159–2165. https://doi.org/10.1039/B104910K
doi: 10.1039/B104910K
Kaljurand, I., Kutt, A., Soovali, L., Rodima, T., Maemets, V., Leito, I., et al. (2005). Extension of the self-consistent spectrophotometric basicity scale in acetonitrile to a full span of 28 pKa units: Unification of different basicity scales. Journal of Organic Chemistry, 70(3), 1019–1028. https://doi.org/10.1021/jo048252w
doi: 10.1021/jo048252w
Khade, R. V., Dutta Choudhury, S., Pal, H., & Kumbhar, A. S. (2018). Excited State Interaction of Ruthenium (II) Imidazole Phenanthroline Complex [Ru(bpy)2ipH]2+ with 1,4-Benzoquinone: Simple Electron Transfer or Proton-Coupled Electron Transfer? ChemPhysChem, 19(18), 2380–2388. https://doi.org/10.1002/cphc.201800313
doi: 10.1002/cphc.201800313
pubmed: 29873437
Giordano, P. J., Bock, C. R., Wrighton, M. S., Interrante, L. V., & Williams, R. F. X. (1977). Excited state proton transfer of a metal complex: Determination of the acid dissociation constant for a metal-to-ligand charge transfer state of a ruthenium(II) complex. Journal of the American Chemical Society, 99(9), 3187–3189. https://doi.org/10.1021/ja00451a066
doi: 10.1021/ja00451a066
Marciniak, B., Kozubek, H., & Paszyc, S. (1992). Estimation of pKa* in the first excited singlet state. A physical chemistry experiment that explores acid-base properties in the excited state. Journal of Chemical Education, 69(3), 247. https://doi.org/10.1021/ed069p247
doi: 10.1021/ed069p247
Weller, A. (1982). Photoinduced electron transfer in solution: Exciplex and radical ion pair formation free enthalpies and their solvent dependence. Zeitschrift für Physikalische Chemie, 133(1), 93–98. https://doi.org/10.1524/zpch.1982.133.1.093
doi: 10.1524/zpch.1982.133.1.093
Rumble, C. A., Licari, G., & Vauthey, E. (2020). Molecular dynamics simulations of bimolecular electron transfer: Testing the coulomb term in the weller equation. The Journal of Physical Chemistry B, 124(44), 9945–9950. https://doi.org/10.1021/acs.jpcb.0c09031
doi: 10.1021/acs.jpcb.0c09031
pubmed: 33095013
Tyburski, R., Liu, T., Glover, S. D., & Hammarstrom, L. (2021). Proton-coupled electron transfer guidelines, fair and square. Journal of the American Chemical Society, 143(2), 560–576. https://doi.org/10.1021/jacs.0c09106
doi: 10.1021/jacs.0c09106
pubmed: 33405896
pmcid: 7880575
Mayer, J. M., & Rhile, I. J. (2004). Thermodynamics and kinetics of proton-coupled electron transfer: stepwise vs.concerted pathways. Biochimica et Biophysica Acta, 1655(1–3), 51–58. https://doi.org/10.1016/j.bbabio.2003.07.002
doi: 10.1016/j.bbabio.2003.07.002
pubmed: 15100016
Tommos, C., & Babcock, G. T. (2000). Proton and hydrogen currents in photosynthetic water oxidation. Biochimica et Biophysica Acta, 1458(1), 199–219. https://doi.org/10.1016/s0005-2728(00)00069-4
doi: 10.1016/s0005-2728(00)00069-4
pubmed: 10812034
Yoneda, Y., Mora, S. J., Shee, J., Wadsworth, B. L., Arsenault, E. A., Hait, D., et al. (2021). Electron-nuclear dynamics accompanying proton-coupled electron transfer. Journal of the American Chemical Society, 143(8), 3104–3112. https://doi.org/10.1021/jacs.0c10626
doi: 10.1021/jacs.0c10626
pubmed: 33601880
Huynh, M. T., Mora, S. J., Villalba, M., Tejeda-Ferrari, M. E., Liddell, P. A., Cherry, B. R., et al. (2017). Concerted one-electron two-proton transfer processes in models inspired by the Tyr-his couple of photosystem II. ACS Central Science, 3(5), 372–380. https://doi.org/10.1021/acscentsci.7b00125
doi: 10.1021/acscentsci.7b00125
pubmed: 28573198
pmcid: 5445534
Zhang, M.-T., Irebo, T., Johansson, O., & Hammarström, L. (2011). Proton-coupled electron transfer from tyrosine: A strong rate dependence on intramolecular proton transfer distance. Journal of the American Chemical Society, 133(34), 13224–13227. https://doi.org/10.1021/ja203483j
doi: 10.1021/ja203483j
pubmed: 21812404
Hammarström, L., & Styring, S. (2011). Proton-coupled electron transfer of tyrosines in Photosystem II and model systems for artificial photosynthesis: the role of a redox-active link between catalyst and photosensitizer. Energy & Environmental Science, 4(7), 2379–2388. https://doi.org/10.1039/C1EE01348C
doi: 10.1039/C1EE01348C
Irebo, T., Reece, S. Y., Sjödin, M., Nocera, D. G., & Hammarström, L. (2007). Proton-coupled electron transfer of tyrosine oxidation: Buffer dependence and parallel mechanisms. Journal of the American Chemical Society, 129(50), 15462–15464. https://doi.org/10.1021/ja073012u
doi: 10.1021/ja073012u
pubmed: 18027937
Magnuson, A., Berglund, H., Korall, P., Hammarstrom, L., Akermark, B., Styring, S., et al. (1997). Mimicking electron transfer reactions in photosystem II: Synthesis and photochemical characterization of a ruthenium(II) tris(bipyridyl) complex with a covalently linked tyrosine. Journal of the American Chemical Society, 119(44), 10720–10725.
doi: 10.1021/ja972161h
Karlsson, S., Boixel, J., Pellegrin, Y., Blart, E., Becker, H.-C., Odobel, F., et al. (2012). Accumulative electron transfer: Multiple charge separation in artificial photosynthesis. Faraday Discussions, 155, 233–252. https://doi.org/10.1039/C1FD00089F
doi: 10.1039/C1FD00089F
pubmed: 22470977