Phosphonate-Derivatized Porphyrins for Photoelectrochemical Applications

Nayak, Animesh; Roy, Subhangi; Sherman, Benjamin D.; Alibabaei, Leila; Lapides, Alexander M.; Brennaman, M. Kyle; Wee, Kyung-Ryang; Meyer, Thomas J.

doi:10.1021/acsami.5b10587

Title: Phosphonate-Derivatized Porphyrins for Photoelectrochemical Applications

Journal Article · Wed Jan 20 00:00:00 EST 2016 · ACS Applied Materials and Interfaces

DOI:https://doi.org/10.1021/acsami.5b10587· OSTI ID:1371162

Nayak, Animesh ^[1]; Roy, Subhangi ^[1]; Sherman, Benjamin D. ^[1]; Alibabaei, Leila ^[1]; Lapides, Alexander M. ^[1]; Brennaman, M. Kyle ^[1]; Wee, Kyung-Ryang ^[1]; Meyer, Thomas J. ^[1]

Univ. of North Carolina, Chapel Hill, NC (United States)

A series of phosphonate-derivatized, high redox potential porphyrins with mesityl, pentafluorophenyl, and heptafluoropropyl meso-substituents were synthesized by acid-catalyzed condensation reactions. Ground and excited state redox potentials in the series were varied systematically with the electron-donating or electron-accepting nature of the meso-substitutents. Here, the extent of excitation and injection by porphyrin singlet excited states surface-bound to SnO₂/TiO₂ core/shell metal oxide nanoparticle films varies with the excited state reduction potential, E°'(P+/P*). Furthermore, with the mesityl-substituted porphyrin, high current density and sustained photocurrents are observed at pH 7 with the addition of the electron transfer donor hydroquinone.

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Solar Fuels (UNC EFRC)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); Department of Defense (DoD); National Defense Science & Engineering Graduate Fellowship (NDSEG) Program

Grant/Contract Number:: SC0001011; CHE-1362481

OSTI ID:: 1371162

Journal Information:: ACS Applied Materials and Interfaces, Vol. 8, Issue 6; Related Information: UNC partners with University of North Carolina (lead); Duke University; University of Florida; Georgia Institute of Technology; University; North Carolina Central University; Research Triangle Institute; ISSN 1944-8244

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 26 works

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References (36)

Design and development of photoanodes for water-splitting dye-sensitized photoelectrochemical cells Swierk, John R.; Mallouk, Thomas E. Chem. Soc. Rev., Vol. 42, Issue 6 https://doi.org/10.1039/C2CS35246J	journal	January 2013
Chemical approaches to artificial photosynthesis Concepcion, J. J.; House, R. L.; Papanikolas, J. M. Proceedings of the National Academy of Sciences, Vol. 109, Issue 39 https://doi.org/10.1073/pnas.1212254109	journal	September 2012
Solar Fuels via Artificial Photosynthesis Gust, Devens; Moore, Thomas A.; Moore, Ana L. Accounts of Chemical Research, Vol. 42, Issue 12 https://doi.org/10.1021/ar900209b	journal	December 2009
Chemical Approaches to Artificial Photosynthesis. 2 Alstrum-Acevedo, James H.; Brennaman, M. Kyle; Meyer, Thomas J. Inorganic Chemistry, Vol. 44, Issue 20 https://doi.org/10.1021/ic050904r	journal	October 2005
Meso-Substituted Porphyrins for Dye-Sensitized Solar Cells Urbani, Maxence; Grätzel, Michael; Nazeeruddin, Mohammad Khaja Chemical Reviews, Vol. 114, Issue 24 https://doi.org/10.1021/cr5001964	journal	November 2014
Porphyrins for dye-sensitised solar cells: new insights into efficiency-determining electron transfer steps Griffith, Matthew J.; Sunahara, Kenji; Wagner, Pawel Chemical Communications, Vol. 48, Issue 35 https://doi.org/10.1039/c2cc30677h	journal	January 2012
Electron Injection Dynamics from Photoexcited Porphyrin Dyes into SnO ₂ and TiO ₂ Nanoparticles Milot, Rebecca L.; Moore, Gary F.; Crabtree, Robert H. The Journal of Physical Chemistry C, Vol. 117, Issue 42 https://doi.org/10.1021/jp406734t	journal	October 2013
Bioinspired High-Potential Porphyrin Photoanodes Moore, Gary F.; Konezny, Steven J.; Song, Hee-eun The Journal of Physical Chemistry C, Vol. 116, Issue 7 https://doi.org/10.1021/jp210096m	journal	February 2012
Metal-free organic sensitizers for use in water-splitting dye-sensitized photoelectrochemical cells Swierk, John R.; Méndez-Hernández, Dalvin D.; McCool, Nicholas S. Proceedings of the National Academy of Sciences, Vol. 112, Issue 6 https://doi.org/10.1073/pnas.1414901112	journal	January 2015
Porphyrin-sensitized solar cells Li, Lu-Lin; Diau, Eric Wei-Guang Chem. Soc. Rev., Vol. 42, Issue 1 https://doi.org/10.1039/C2CS35257E	journal	January 2013
A visible light water-splitting cell with a photoanode formed by codeposition of a high-potential porphyrin and an iridium water-oxidation catalyst Moore, Gary F.; Blakemore, James D.; Milot, Rebecca L. Energy & Environmental Science, Vol. 4, Issue 7 https://doi.org/10.1039/c1ee01037a	journal	January 2011
Efficient Solar Cells Sensitized by Porphyrins with an Extended Conjugation Framework and a Carbazole Donor: From Molecular Design to Cosensitization Wang, Yueqiang; Chen, Bin; Wu, Wenjun Angewandte Chemie International Edition, Vol. 53, Issue 40 https://doi.org/10.1002/anie.201406190	journal	August 2014
Porphyrin Cosensitization for a Photovoltaic Efficiency of 11.5%: A Record for Non-Ruthenium Solar Cells Based on Iodine Electrolyte Xie, Yongshu; Tang, Yunyu; Wu, Wenjun Journal of the American Chemical Society, Vol. 137, Issue 44 https://doi.org/10.1021/jacs.5b09665	journal	October 2015
Visible photoelectrochemical water splitting into H ₂ and O ₂ in a dye-sensitized photoelectrosynthesis cell Alibabaei, Leila; Sherman, Benjamin D.; Norris, Michael R. Proceedings of the National Academy of Sciences, Vol. 112, Issue 19 https://doi.org/10.1073/pnas.1506111112	journal	April 2015
Nanoporous SnO2 electrodes for dye-sensitized solar cells: improved cell performance by the synthesis of 18nm SnO2 colloids Chappel, S.; Zaban, A. Solar Energy Materials and Solar Cells, Vol. 71, Issue 2 https://doi.org/10.1016/S0927-0248(01)00050-2	journal	February 2002
Investigation of Conditions Giving Minimal Scrambling in the Synthesis of trans -Porphyrins from Dipyrromethanes and Aldehydes Littler, Benjamin J.; Ciringh, Yangzhen; Lindsey, Jonathan S. The Journal of Organic Chemistry, Vol. 64, Issue 8 https://doi.org/10.1021/jo982452o	journal	April 1999
One-flask synthesis of meso-substituted dipyrromethanes and their application in the synthesis of trans-substituted porphyrin building blocks Lee, Chang-Hee; S. Lindsey, Jonathan Tetrahedron, Vol. 50, Issue 39 https://doi.org/10.1016/S0040-4020(01)89282-6	journal	January 1994
Porphyrins Bearing Arylphosphonic Acid Tethers for Attachment to Oxide Surfaces Muthukumaran, Kannan; Loewe, Robert S.; Ambroise, Arounaguiry The Journal of Organic Chemistry, Vol. 69, Issue 5 https://doi.org/10.1021/jo034945l	journal	March 2004
Polyporphyrin Thin Films from the Interfacial Polymerization of Mercaptoporphyrins Wen, Liqin; Li, Ming; Schlenoff, Joseph B. Journal of the American Chemical Society, Vol. 119, Issue 33 https://doi.org/10.1021/ja970612s	journal	August 1997
Synthesis and Supramolecular Properties of a Novel Octaphosphonate Porphyrin Bhosale, Sheshanath V.; Kalyankar, Mohan B.; Langford, Steven J. European Journal of Organic Chemistry, Vol. 2009, Issue 24 https://doi.org/10.1002/ejoc.200900589	journal	August 2009
A Scalable Synthesis of Meso-Substituted Dipyrromethanes Laha, Joydev K.; Dhanalekshmi, Savithri; Taniguchi, Masahiko Organic Process Research & Development, Vol. 7, Issue 6 https://doi.org/10.1021/op034083q	journal	November 2003
Synthesis and photophysical characterization of porphyrin and porphyrin–Ru(ii) polypyridyl chromophore–catalyst assemblies on mesoporous metal oxides Nayak, Animesh; Knauf, Robin R.; Hanson, Kenneth Chemical Science, Vol. 5, Issue 8 https://doi.org/10.1039/c4sc00875h	journal	January 2014
Phosphonate- and Carboxylate-Based Self-Assembled Monolayers for Organic Devices: A Theoretical Study of Surface Binding on Aluminum Oxide with Experimental Support Bauer, Thilo; Schmaltz, Thomas; Lenz, Thomas ACS Applied Materials & Interfaces, Vol. 5, Issue 13 https://doi.org/10.1021/am4008374	journal	June 2013
Effects of Surface Anchoring Groups (Carboxylate vs Phosphonate) in Ruthenium-Complex-Sensitized TiO ₂ on Visible Light Reactivity in Aqueous Suspensions Bae, Eunyoung; Choi, Wonyong; Park, Jaiwook The Journal of Physical Chemistry B, Vol. 108, Issue 37 https://doi.org/10.1021/jp047777p	journal	September 2004
Effect of the Anchoring Group (Carboxylate vs Phosphonate) in Ru-Complex-Sensitized TiO₂ on Hydrogen Production under Visible Light Bae, Eunyoung; Choi, Wonyong The Journal of Physical Chemistry B, Vol. 110, Issue 30, p. 14792-14799 https://doi.org/10.1021/jp062540+	journal	July 2006
Photostability of Phosphonate-Derivatized, Ru ^II Polypyridyl Complexes on Metal Oxide Surfaces Hanson, Kenneth; Brennaman, M. Kyle; Luo, Hanlin ACS Applied Materials & Interfaces, Vol. 4, Issue 3 https://doi.org/10.1021/am201717x	journal	February 2012
A porphyrin-stabilized iridium oxide water oxidation catalyst Sherman, Benjamin D.; Pillai, Smitha; Kodis, Gerdenis Canadian Journal of Chemistry, Vol. 89, Issue 2 https://doi.org/10.1139/V10-118	journal	February 2011
Layer-by-layer assembly and intercalation reactions of iron(III) and iron(II) alkanebisphosphonates on gold surfaces Feldheim, Daniel L.; Mallouk, Thomas E. Chemical Communications, Issue 22 https://doi.org/10.1039/cc9960002591	journal	January 1996
Self-Assembled Bilayer Films of Ruthenium(II)/Polypyridyl Complexes through Layer-by-Layer Deposition on Nanostructured Metal Oxides Hanson, Kenneth; Torelli, Daniel A.; Vannucci, Aaron K. Angewandte Chemie International Edition, Vol. 51, Issue 51 https://doi.org/10.1002/anie.201206882	journal	November 2012
Electric Conduction Properties of Self-assembled Monolayer Films of Ru Complexes with Disulfide/Phosphonate Anchors in a Au–(Molecular Ensemble)–(Au Nanoparticle) Junction Terada, Keiichi; Kobayashi, Katsuaki; Hikita, Jiro Chemistry Letters, Vol. 38, Issue 5 https://doi.org/10.1246/cl.2009.416	journal	May 2009
Photoelectrochemical cells Grätzel, Michael Nature, Vol. 414, Issue 6861 https://doi.org/10.1038/35104607	journal	November 2001
Photophysical properties of sixty atom carbon molecule (C60) Arbogast, James W.; Darmanyan, Aleksander P.; Foote, Christopher S. The Journal of Physical Chemistry, Vol. 95, Issue 1 https://doi.org/10.1021/j100154a006	journal	January 1991
Porphyrins. 40. Electronic spectra and four-orbital energies of free-base, zinc, copper, and palladium tetrakis(perfluorophenyl)porphyrins Spellane, P. J.; Gouterman, M.; Antipas, A. Inorganic Chemistry, Vol. 19, Issue 2 https://doi.org/10.1021/ic50204a021	journal	February 1980
Parameters affecting the chemical work output of a hybrid photoelectrochemical biofuel cell Hambourger, Michael; Liddell, Paul A.; Gust, Devens Photochemical & Photobiological Sciences, Vol. 6, Issue 4 https://doi.org/10.1039/b616444g	journal	January 2007
Atomic Layer Deposition of TiO ₂ on Mesoporous nanoITO: Conductive Core–Shell Photoanodes for Dye-Sensitized Solar Cells Alibabaei, Leila; Farnum, Byron H.; Kalanyan, Berç Nano Letters, Vol. 14, Issue 6 https://doi.org/10.1021/nl5006433	journal	May 2014
Solar water splitting in a molecular photoelectrochemical cell Alibabaei, L.; Brennaman, M. K.; Norris, M. R. Proceedings of the National Academy of Sciences, Vol. 110, Issue 50 https://doi.org/10.1073/pnas.1319628110	journal	November 2013

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Electrocatalytic reduction of CO ₂ with CCC-NHC pincer nickel complexes Cope, James D.; Liyanage, Nalaka P.; Kelley, Paul J. Chemical Communications, Vol. 53, Issue 68 https://doi.org/10.1039/c6cc06537f	journal	January 2017
Fabrication of carbon nanotube-multiporphyrin array composites as light-sensitizer for photocurrent generation, photochromism of viologen and catalytic degradation of methyl orange Wang, Jing; He, Wen-Li; Chen, Meng New Journal of Chemistry, Vol. 42, Issue 21 https://doi.org/10.1039/c8nj03780a	journal	January 2018

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
catalysis (homogeneous)
catalysis (heterogeneous)
solar (photovoltaic)
solar (fuels)
photosynthesis (natural and artificial)
hydrogen and fuel cells
electrodes - solar
charge transport
materials and chemistry by design
synthesis (novel materials)
synthesis (self-assembly)
porphyrin
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excited state potential

Title: Phosphonate-Derivatized Porphyrins for Photoelectrochemical Applications

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