Electron Transfer from Photoexcited Naphthalene Diimide Radical Anion to Electrocatalytically Active Re(bpy)(CO)3 Cl in a Molecular Triad
Abstract
Electron donor–acceptor photosensitizers having long charge separation lifetimes and high-reducing potentials that can be easily appended to thermodynamically difficult to reduce catalysts hold great promise for driving CO2 reduction. We introduce a new molecular triad utilizing a naphthalene diimide radical anion (NDI•–) donor chromophore appended to a 9,10-diphenylanthracene (DPA) acceptor, which is in turn linked to Re(bpy)(CO)3Cl. The NDI•– chromophore is readily generated by mild chemical or electrochemical reduction, absorbs at wavelengths as long as 800 nm, and has an excited state oxidation potential (–2.1 V vs SCE), which rivals or exceeds those of metalorganic and organometallic chromophores. Photoexcitation of NDI•– to *NDI•– is followed by ultrafast reduction of DPA to DPA•–, which then rapidly reduces the metal complex. The overall quantum yield for reduction of Re(bpy)(CO)3Cl is approximately 90% using visible light. The general time constant for the forward electron transfer to reduce the metal complex is τ = 14.5 ps, while the time constant for back-electron transfer is τ = 24.5 ns. Under typical electrocatalytic conditions, the molecular triad demonstrates electrochemical reduction of CO2.
- Authors:
-
[1];
[1]
- Northwestern Univ., Evanston, IL (United States). Dept. of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center
- Publication Date:
- Research Org.:
- Northwestern Univ., Evanston, IL (United States). Energy Frontier Research Center (EFRC) Argonne-Northwestern Solar Energy Research (ANSER) Center
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
- OSTI Identifier:
- 1470239
- Grant/Contract Number:
- SC0001059
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Physical Chemistry. C
- Additional Journal Information:
- Journal Volume: 122; Journal Issue: 5; Related Information: ANSER partners with Northwestern University (lead); Argonne National Laboratory; University of Chicago; University of Illinois, Urbana-Champaign; Yale University; Journal ID: ISSN 1932-7447
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 71 CLASSICAL AND QUANTUM MECHANICS, GENERAL PHYSICS; 14 SOLAR ENERGY
Citation Formats
Martinez, Jose F., La Porte, Nathan T., and Wasielewski, Michael R. Electron Transfer from Photoexcited Naphthalene Diimide Radical Anion to Electrocatalytically Active Re(bpy)(CO)3 Cl in a Molecular Triad. United States: N. p., 2018.
Web. doi:10.1021/acs.jpcc.7b11999.
Martinez, Jose F., La Porte, Nathan T., & Wasielewski, Michael R. Electron Transfer from Photoexcited Naphthalene Diimide Radical Anion to Electrocatalytically Active Re(bpy)(CO)3 Cl in a Molecular Triad. United States. https://doi.org/10.1021/acs.jpcc.7b11999
Martinez, Jose F., La Porte, Nathan T., and Wasielewski, Michael R. Fri .
"Electron Transfer from Photoexcited Naphthalene Diimide Radical Anion to Electrocatalytically Active Re(bpy)(CO)3 Cl in a Molecular Triad". United States. https://doi.org/10.1021/acs.jpcc.7b11999. https://www.osti.gov/servlets/purl/1470239.
@article{osti_1470239,
title = {Electron Transfer from Photoexcited Naphthalene Diimide Radical Anion to Electrocatalytically Active Re(bpy)(CO)3 Cl in a Molecular Triad},
author = {Martinez, Jose F. and La Porte, Nathan T. and Wasielewski, Michael R.},
abstractNote = {Electron donor–acceptor photosensitizers having long charge separation lifetimes and high-reducing potentials that can be easily appended to thermodynamically difficult to reduce catalysts hold great promise for driving CO2 reduction. We introduce a new molecular triad utilizing a naphthalene diimide radical anion (NDI•–) donor chromophore appended to a 9,10-diphenylanthracene (DPA) acceptor, which is in turn linked to Re(bpy)(CO)3Cl. The NDI•– chromophore is readily generated by mild chemical or electrochemical reduction, absorbs at wavelengths as long as 800 nm, and has an excited state oxidation potential (–2.1 V vs SCE), which rivals or exceeds those of metalorganic and organometallic chromophores. Photoexcitation of NDI•– to *NDI•– is followed by ultrafast reduction of DPA to DPA•–, which then rapidly reduces the metal complex. The overall quantum yield for reduction of Re(bpy)(CO)3Cl is approximately 90% using visible light. The general time constant for the forward electron transfer to reduce the metal complex is τ = 14.5 ps, while the time constant for back-electron transfer is τ = 24.5 ns. Under typical electrocatalytic conditions, the molecular triad demonstrates electrochemical reduction of CO2.},
doi = {10.1021/acs.jpcc.7b11999},
journal = {Journal of Physical Chemistry. C},
number = 5,
volume = 122,
place = {United States},
year = {2018},
month = {1}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 10 works
Citation information provided by
Web of Science
Web of Science
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Mimicking Photosynthetic Solar Energy Transduction
journal, January 2001
- Gust, Devens; Moore, Thomas A.; Moore, Ana L.
- Accounts of Chemical Research, Vol. 34, Issue 1
Accumulative Charge Separation for Solar Fuels Production: Coupling Light-Induced Single Electron Transfer to Multielectron Catalysis
journal, February 2015
- Hammarström, Leif
- Accounts of Chemical Research, Vol. 48, Issue 3
Light Absorption and Energy Transfer in the Antenna Complexes of Photosynthetic Organisms
journal, March 2016
- Mirkovic, Tihana; Ostroumov, Evgeny E.; Anna, Jessica M.
- Chemical Reviews, Vol. 117, Issue 2
A Place in the Sun for Artificial Photosynthesis?
journal, May 2016
- Su, Jinzhan; Vayssieres, Lionel
- ACS Energy Letters, Vol. 1, Issue 1
Chemical Approaches to Artificial Photosynthesis. 2
journal, October 2005
- Alstrum-Acevedo, James H.; Brennaman, M. Kyle; Meyer, Thomas J.
- Inorganic Chemistry, Vol. 44, Issue 20
Photo-induced electron and energy transfer in non-covalently bonded supramolecular assemblies
journal, January 1997
- Ward, Michael D.
- Chemical Society Reviews, Vol. 26, Issue 5
Photoinduced electron transfer in supramolecular systems for artificial photosynthesis
journal, May 1992
- Wasielewski, Michael R.
- Chemical Reviews, Vol. 92, Issue 3, p. 435-461
Primary electron acceptors in plant photosynthesis
journal, November 1980
- Fajer, J.; Davis, M. S.; Forman, A.
- Journal of the American Chemical Society, Vol. 102, Issue 23
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
journal, January 2011
- Hammarström, Leif; Styring, Stenbjörn
- Energy & Environmental Science, Vol. 4, Issue 7
Distribution and dynamics of electron transport complexes in cyanobacterial thylakoid membranes
journal, March 2016
- Liu, Lu-Ning
- Biochimica et Biophysica Acta (BBA) - Bioenergetics, Vol. 1857, Issue 3
The photophysics of photoredox catalysis: a roadmap for catalyst design
journal, January 2016
- Arias-Rotondo, Daniela M.; McCusker, James K.
- Chemical Society Reviews, Vol. 45, Issue 21
Supramolecular Photocatalysts for the Reduction of CO 2
journal, April 2017
- Tamaki, Yusuke; Ishitani, Osamu
- ACS Catalysis, Vol. 7, Issue 5
Sacrificial electron donor reagents for solar fuel production
journal, March 2017
- Pellegrin, Yann; Odobel, Fabrice
- Comptes Rendus Chimie, Vol. 20, Issue 3
Electron Transfer from the Porphyrin S 2 State in a Zinc Porphyrin-Rhenium Bipyridyl Dyad having Carbon Dioxide Reduction Activity
journal, May 2009
- Kiyosawa, Kuniomi; Shiraishi, Naoki; Shimada, Tetsuya
- The Journal of Physical Chemistry C, Vol. 113, Issue 27
Detection of a charge-separated catalyst precursor state in a linked photosensitizer-catalyst assembly
journal, January 2013
- Mukherjee, Anusree; Kokhan, Oleksandr; Huang, Jier
- Physical Chemistry Chemical Physics, Vol. 15, Issue 48
Light-Driven Hydrogen Evolution by BODIPY-Sensitized Cobaloxime Catalysts
journal, April 2014
- Bartelmess, Juergen; Francis, Aaron J.; El Roz, Karim A.
- Inorganic Chemistry, Vol. 53, Issue 9
Ultrafast Charge Separation in a Photoreactive Rhenium-Appended Porphyrin Assembly Monitored by Picosecond Transient Infrared Spectroscopy
journal, April 2006
- Gabrielsson, Anders; Hartl, František; Zhang, Hong
- Journal of the American Chemical Society, Vol. 128, Issue 13
Remote site photosubstitution in metalloporphyrin–rhenium tricarbonylbipyridine assemblies: photo-reactions of molecules with very short lived excited states
journal, January 2008
- Gabrielsson, Anders; Lindsay Smith, John R.; Perutz, Robin N.
- Dalton Transactions, Issue 32
CO2 photoreduction with long-wavelength light: dyads and monomers of zinc porphyrin and rhenium bipyridine
journal, January 2012
- Windle, Christopher D.; Câmpian, Marius V.; Duhme-Klair, Anne-K.
- Chemical Communications, Vol. 48, Issue 66
Comparison of rhenium–porphyrin dyads for CO 2 photoreduction: photocatalytic studies and charge separation dynamics studied by time-resolved IR spectroscopy
journal, January 2015
- Windle, Christopher D.; George, Michael W.; Perutz, Robin N.
- Chemical Science, Vol. 6, Issue 12
A novel ruthenium(II) tris(bipyridine)–zinc porphyrin–rhenium carbonyl triad: synthesis and optical properties
journal, April 2006
- Liu, Xien; Liu, Jianhui; Pan, Jingxi
- Tetrahedron, Vol. 62, Issue 15
Photo-induced ligand substitution at a remote site via electron transfer in a porphyrin-appended rhenium carbonyl supermoleculeElectronic supplementary information (ESI) available: energy balance, synthesis and characterisation of 1+OTf– and fluorescence spectra of 1+, 2 and 5. See http://www.rsc.org/suppdata/cc/b2/b200127f/
journal, April 2002
- Gabrielsson, Anders; Hartl, Frantis̆ek; Smith, John R. Lindsay
- Chemical Communications, Issue 9
CO 2 Capture by a Rhenium(I) Complex with the Aid of Triethanolamine
journal, October 2013
- Morimoto, Tatsuki; Nakajima, Takuya; Sawa, Shuhei
- Journal of the American Chemical Society, Vol. 135, Issue 45
Architecture of Supramolecular Metal Complexes for Photocatalytic CO 2 Reduction: Ruthenium−Rhenium Bi- and Tetranuclear Complexes
journal, April 2005
- Gholamkhass, Bobak; Mametsuka, Hiroaki; Koike, Kazuhide
- Inorganic Chemistry, Vol. 44, Issue 7
Substantial improvement in the efficiency and durability of a photocatalyst for carbon dioxide reduction using a benzoimidazole derivative as an electron donor
journal, August 2013
- Tamaki, Yusuke; Koike, Kazuhide; Morimoto, Tatsuki
- Journal of Catalysis, Vol. 304
Development of highly efficient supramolecular CO 2 reduction photocatalysts with high turnover frequency and durability
journal, January 2012
- Tamaki, Yusuke; Watanabe, Katsuhiro; Koike, Kazuhide
- Faraday Discuss., Vol. 155
Architecture of supramolecular metal complexes for photocatalytic CO2 reduction
journal, September 2009
- Koike, Kazuhide; Naito, Sayoko; Sato, Shunsuke
- Journal of Photochemistry and Photobiology A: Chemistry, Vol. 207, Issue 1
Highly efficient supramolecular photocatalysts for CO 2 reduction using visible light
journal, January 2007
- Sato, Shunsuke; Koike, Kazuhide; Inoue, Haruo
- Photochem. Photobiol. Sci., Vol. 6, Issue 4
Photoinduced electron transfer from rylenediimide radical anions and dianions to Re(bpy)(CO) 3 using red and near-infrared light
journal, January 2017
- La Porte, Nathan T.; Martinez, Jose F.; Hedström, Svante
- Chemical Science, Vol. 8, Issue 5
Photo-driven electron transfer from the highly reducing excited state of naphthalene diimide radical anion to a CO 2 reduction catalyst within a molecular triad
journal, January 2017
- Martinez, Jose F.; La Porte, Nathan T.; Mauck, Catherine M.
- Faraday Discussions, Vol. 198
Mechanistic Contrasts between Manganese and Rhenium Bipyridine Electrocatalysts for the Reduction of Carbon Dioxide
journal, November 2014
- Riplinger, Christoph; Sampson, Matthew D.; Ritzmann, Andrew M.
- Journal of the American Chemical Society, Vol. 136, Issue 46
Excited Doublet States of Electrochemically Generated Aromatic Imide and Diimide Radical Anions
journal, July 2000
- Gosztola, David; Niemczyk, Mark P.; Svec, Walter
- The Journal of Physical Chemistry A, Vol. 104, Issue 28
Mechanisms for CO Production from CO 2 Using Reduced Rhenium Tricarbonyl Catalysts
journal, March 2012
- Agarwal, Jay; Fujita, Etsuko; Schaefer, Henry F.
- Journal of the American Chemical Society, Vol. 134, Issue 11
Chemical Redox Agents for Organometallic Chemistry
journal, January 1996
- Connelly, Neil G.; Geiger, William E.
- Chemical Reviews, Vol. 96, Issue 2
Ultrafast Conformational Dynamics of Electron Transfer in ExBox 4+ ⊂Perylene
journal, November 2013
- Young, Ryan M.; Dyar, Scott M.; Barnes, Jonathan C.
- The Journal of Physical Chemistry A, Vol. 117, Issue 47
Picosecond Control of Photogenerated Radical Pair Lifetimes Using a Stable Third Radical
journal, April 2016
- Horwitz, Noah E.; Phelan, Brian T.; Nelson, Jordan N.
- The Journal of Physical Chemistry A, Vol. 120, Issue 18
Optical parametric amplification of femtosecond pulses tunable from the blue to the infrared with microjoule energies
journal, January 1995
- Greenfield, Scott R.; Wasielewski, Michael R.
- Applied Optics, Vol. 34, Issue 15
Near-transform-limited visible and near-IR femtosecond pulses from optical parametric amplification using Type II β-barium borate
journal, January 1995
- Greenfield, Scott R.; Wasielewski, Michael R.
- Optics Letters, Vol. 20, Issue 12
Advances in molecular quantum chemistry contained in the Q-Chem 4 program package
journal, September 2014
- Shao, Yihan; Gan, Zhengting; Epifanovsky, Evgeny
- Molecular Physics, Vol. 113, Issue 2
Geometries of Third-Row Transition-Metal Complexes from Density-Functional Theory
journal, July 2008
- Bühl, Michael; Reimann, Christoph; Pantazis, Dimitrios A.
- Journal of Chemical Theory and Computation, Vol. 4, Issue 9
Re(bipy-tBu)(CO) 3 Cl−improved Catalytic Activity for Reduction of Carbon Dioxide: IR-Spectroelectrochemical and Mechanistic Studies
journal, October 2010
- Smieja, Jonathan M.; Kubiak, Clifford P.
- Inorganic Chemistry, Vol. 49, Issue 20
Synthesis of mono-substituted 2,2′-bipyridinesElectronic supplementary information (ESI) available: experimental details and full characterization of new compounds. See http://www.rsc.org/suppdata/cc/b2/b203595b/
journal, June 2002
- Cordaro, Joseph G.; McCusker, James K.; Bergman, Robert G.
- Chemical Communications, Issue 14
Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters
journal, November 1995
- Ishiyama, Tatsuo; Murata, Miki; Miyaura, Norio
- The Journal of Organic Chemistry, Vol. 60, Issue 23, p. 7508-7510
Supramolecular electrochemistry
journal, March 1991
- Roffia, Sergio; Casadei, Roberto; Paolucci, Francesco
- Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 302, Issue 1-2
Elucidation of the Selectivity of Proton-Dependent Electrocatalytic CO 2 Reduction by fac -Re(bpy)(CO) 3 Cl
journal, October 2013
- Keith, John A.; Grice, Kyle A.; Kubiak, Clifford P.
- Journal of the American Chemical Society, Vol. 135, Issue 42
Solubility and electrochemical determination of CO2 in some dipolar aprotic solvents
journal, August 1990
- Gennaro, Armando; Isse, Abdirisak Ahmed; Vianello, Elio
- Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 289, Issue 1-2
Kinetic and structural studies, origins of selectivity, and interfacial charge transfer in the artificial photosynthesis of CO
journal, May 2012
- Smieja, J. M.; Benson, E. E.; Kumar, B.
- Proceedings of the National Academy of Sciences, Vol. 109, Issue 39
Electrochemical and mechanistic studies of Re(CO)3(dmbpy)CI] and their relation to the catalytic reduction of CO2
journal, April 1986
- Breikss, Anne I.; Abruña, Hector D.
- Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 201, Issue 2
Efficient photochemical reduction of CO 2 to CO by visible light irradiation of systems containing Re(bipy)(CO) 3 X or Ru(bipy) 3 2+ –Co 2+ combinations as homogeneous catalysts
journal, January 1983
- Hawecker, Jeannot; Lehn, Jean-Marie; Ziessel, Raymond
- J. Chem. Soc., Chem. Commun., Issue 9
One- and two-electron pathways in the electrocatalytic reduction of CO 2 by fac-Re(bpy)(CO) 3 Cl (bpy = 2,2′-bipyridine)
journal, January 1985
- Sullivan, B. Patrick; Bolinger, C. Mark; Conrad, David
- J. Chem. Soc., Chem. Commun., Issue 20
Mechanism of Photocatalytic Reduction of CO 2 by Re(bpy)(CO) 3 Cl from Differences in Carbon Isotope Discrimination
journal, July 2016
- Schneider, Taylor W.; Ertem, Mehmed Z.; Muckerman, James T.
- ACS Catalysis, Vol. 6, Issue 8
Involvement of a Binuclear Species with the Re−C(O)O−Re Moiety in CO 2 Reduction Catalyzed by Tricarbonyl Rhenium(I) Complexes with Diimine Ligands: Strikingly Slow Formation of the Re−Re and Re−C(O)O−Re Species from Re(dmb)(CO) 3 S (dmb = 4,4‘-Dimethyl-2,2‘-bipyridine, S = Solvent)
journal, October 2003
- Hayashi, Yukiko; Kita, Shouichi; Brunschwig, Bruce S.
- Journal of the American Chemical Society, Vol. 125, Issue 39
Direct observation of the reduction of carbon dioxide by rhenium bipyridine catalysts
journal, January 2013
- Sampson, Matthew D.; Froehlich, Jesse D.; Smieja, Jonathan M.
- Energy & Environmental Science, Vol. 6, Issue 12
Carbon monoxide release catalysed by electron transfer: electrochemical and spectroscopic investigations of [Re(bpy-R)(CO)4](OTf) complexes relevant to CO2 reduction
journal, January 2013
- Grice, Kyle A.; Gu, Nina X.; Sampson, Matthew D.
- Dalton Transactions, Vol. 42, Issue 23
The Electronic States of Rhenium Bipyridyl Electrocatalysts for CO 2 Reduction as Revealed by X-ray Absorption Spectroscopy and Computational Quantum Chemistry
journal, March 2013
- Benson, Eric E.; Sampson, Matthew D.; Grice, Kyle A.
- Angewandte Chemie International Edition, Vol. 52, Issue 18
Development of an Efficient Photocatalytic System for CO 2 Reduction Using Rhenium(I) Complexes Based on Mechanistic Studies
journal, February 2008
- Takeda, Hiroyuki; Koike, Kazuhide; Inoue, Haruo
- Journal of the American Chemical Society, Vol. 130, Issue 6
A mechanistic investigation of the photoinduced reduction of carbon dioxide mediated by tricarbonylbromo(2,2'-bipyridine)rhenium(I)
journal, December 1985
- Kutal, Charles.; Weber, Michael A.; Ferraudi, Guillermo.
- Organometallics, Vol. 4, Issue 12
Luminescence and redox reactions of the metal-to-ligand charge-transfer excited state of tricarbonylchloro-(polypyridyl)rhenium(I) complexes
journal, January 1986
- Kalyanasundaram, Kuppuswamy
- Journal of the Chemical Society, Faraday Transactions 2, Vol. 82, Issue 12
Photochemistry of [Re(bipy)(CO)3(PPh3)]+ (bipy = 2,2′-bipyridine) in the presence of triethanolamine associated with photoreductive fixation of carbon dioxide: participation of a chain reaction mechanism
journal, January 1997
- Hori, Hisao; Johnson, Frank P. A.; Koike, Kazuhide
- Journal of the Chemical Society, Dalton Transactions, Issue 6
Photodriven hydrogen evolution by molecular catalysts using Al 2 O 3 -protected perylene-3,4-dicarboximide on NiO electrodes
journal, January 2017
- Kamire, Rebecca J.; Majewski, Marek B.; Hoffeditz, William L.
- Chemical Science, Vol. 8, Issue 1
Works referencing / citing this record:
Supramolecular Chiral Helical Ribbons of Tetraphenylethylene-Appended Naphthalenediimide Controlled by Solvent and Induced by l - and d -Alanine Spacers
journal, November 2018
- Goskulwad, Santosh P.; Kobaisi, Mohammad Al; La, Duong Duc
- Chemistry - An Asian Journal, Vol. 13, Issue 24
Hierarchical Self‐Assembly of Pyrene‐Linked Cyclodextrin and Adamantane‐Linked Naphthalene Diimide System: A Case of Inclusion‐Binding‐Assisted Charge‐Transfer Interaction
journal, January 2019
- Jeevan, Athira Kanakkattussery; Gopidas, Karical Raman
- ChemistrySelect, Vol. 4, Issue 2
Electron transfer reactions in sub-porphyrin–naphthyldiimide dyads
journal, January 2019
- Küçüköz, Betül; Adinarayana, B.; Osuka, Atsuhiro
- Physical Chemistry Chemical Physics, Vol. 21, Issue 30
Experimental and computational exploration of photophysical and electroluminescent properties of modified 2,2′:6′,2″-terpyridine, 2,6-di(thiazol-2-yl)pyridine and 2,6-di(pyrazin-2-yl)pyridine ligands and their Re(I) complexes: Photopysics of Re(I) complexes - effect of donor-acceptor ligand
journal, October 2018
- Klemens, Tomasz; Świtlicka, Anna; Szlapa-Kula, Agata
- Applied Organometallic Chemistry, Vol. 32, Issue 12
Covalently linking CuInS 2 quantum dots with a Re catalyst by click reaction for photocatalytic CO 2 reduction
journal, January 2018
- Huang, Jing; Gatty, Mélina Gilbert; Xu, Bo
- Dalton Transactions, Vol. 47, Issue 31