Symmetry-Breaking Charge Transfer of Visible Light Absorbing Systems: Zinc Dipyrrins

Trinh, Cong; Kirlikovali, Kent; Das, Saptaparna; Ener, Maraia E.; Gray, Harry B.; Djurovich, Peter; Bradforth, Stephen E.; Thompson, Mark E.

doi:10.1021/jp506855t

Title: Symmetry-Breaking Charge Transfer of Visible Light Absorbing Systems: Zinc Dipyrrins

Journal Article · Thu Sep 11 00:00:00 EDT 2014 · Journal of Physical Chemistry. C

DOI:https://doi.org/10.1021/jp506855t· OSTI ID:1159174

Trinh, Cong ^[1]; Kirlikovali, Kent ^[1]; Das, Saptaparna ^[1]; Ener, Maraia E. ^[2]; Gray, Harry B. ^[2]; Djurovich, Peter ^[1]; Bradforth, Stephen E. ^[1]; Thompson, Mark E. ^[1]

Department of Chemistry, University of Southern California, Los Angeles, California 90089, United States
California Institute of Technology, 1200 East California Boulevard, Pasadena, California 91125, United States

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Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: DE SC0001013

OSTI ID:: 1159174

Journal Information:: Journal of Physical Chemistry. C, Journal Name: Journal of Physical Chemistry. C Vol. 118 Journal Issue: 38; ISSN 1932-7447

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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References (57)

Light-driven water oxidation for solar fuels Young, Karin J.; Martini, Lauren A.; Milot, Rebecca L. Coordination Chemistry Reviews, Vol. 256, Issue 21-22 https://doi.org/10.1016/j.ccr.2012.03.031	journal	November 2012
BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties Loudet, Aurore; Burgess, Kevin Chemical Reviews, Vol. 107, Issue 11 https://doi.org/10.1021/cr078381n	journal	November 2007
Excited-State Electronic Asymmetry of the Special Pair in Photosynthetic Reaction Center Mutants: Absorption and Stark Spectroscopy ^† Moore, Laura J.; Zhou, Huilin; Boxer, Steven G. Biochemistry, Vol. 38, Issue 37 https://doi.org/10.1021/bi990892j	journal	September 1999
Zipper Assembly of Vectorial Rigid-Rod π-Stack Architectures with Red and Blue Naphthalenediimides: Toward Supramolecular Cascade n/p-Heterojunctions Sisson, Adam L.; Sakai, Naomi; Banerji, Natalie Angewandte Chemie International Edition, Vol. 47, Issue 20 https://doi.org/10.1002/anie.200800203	journal	May 2008
Ultrafast Photoinduced Charge Separation in Naphthalene Diimide Based Multichromophoric Systems in Liquid Solutions and in a Lipid Membrane Banerji, Natalie; Fürstenberg, Alexandre; Bhosale, Sheshanath The Journal of Physical Chemistry B, Vol. 112, Issue 30 https://doi.org/10.1021/jp801276p	journal	July 2008
Synthesis and Characterization of Fluorescent Pyrrolyldipyrrinato Sn(IV) Complexes Crawford, Sarah M.; Al-Sheikh Ali, Adeeb; Cameron, T. Stanley Inorganic Chemistry, Vol. 50, Issue 17 https://doi.org/10.1021/ic200731t	journal	September 2011
Photoproduction of Proton Gradients with π-Stacked Fluorophore Scaffolds in Lipid Bilayers Bhosale, Sheshanath; Sisson, Adam L.; Talukdar, Pinaki Science, Vol. 313, Issue 5783 https://doi.org/10.1126/science.1126524	journal	July 2006
Two Different Charge Transfer States of Photoexcited 9,9′-Bianthryl in Polar and Nonpolar Solvents Characterized by Nanosecond Time-Resolved Near-IR Spectroscopy in the 4500−10 500 cm ⁻¹ Region Asami, Nobuyuki; Takaya, Tomohisa; Yabumoto, Soshi The Journal of Physical Chemistry A, Vol. 114, Issue 22 https://doi.org/10.1021/jp912173h	journal	May 2010
Excited-State Energy-Transfer Dynamics in Self-Assembled Triads Composed of Two Porphyrins and an Intervening Bis(dipyrrinato)metal Complex Yu, Lianhe; Muthukumaran, Kannan; Sazanovich, Igor V. Inorganic Chemistry, Vol. 42, Issue 21 https://doi.org/10.1021/ic034559m	journal	October 2003
Aluminium complexes of N2O2-type dipyrrins: the first hetero-multinuclear complexes of metallo-dipyrrins with high fluorescence quantum yields Ikeda, Chusaku; Ueda, Satoko; Nabeshima, Tatsuya Chemical Communications, Issue 18 https://doi.org/10.1039/b820141b	journal	January 2009
Intersystem Crossing in Halogenated Bodipy Chromophores Used for Solar Hydrogen Production Sabatini, Randy Pat; McCormick, Theresa M.; Lazarides, Theodore The Journal of Physical Chemistry Letters, Vol. 2, Issue 3 https://doi.org/10.1021/jz101697y	journal	January 2011
Independent initiation of primary electron transfer in the two branches of the photosystem I reaction center Muller, M. G.; Slavov, C.; Luthra, R. Proceedings of the National Academy of Sciences, Vol. 107, Issue 9 https://doi.org/10.1073/pnas.0905407107	journal	February 2010
Self-Assembled Nanoscale DNA–Porphyrin Complex for Artificial Light Harvesting Woller, Jakob G.; Hannestad, Jonas K.; Albinsson, Bo Journal of the American Chemical Society, Vol. 135, Issue 7 https://doi.org/10.1021/ja311828v	journal	February 2013
Evidence for a very early intermediate in bacterial photosynthesis. A photon-echo and hole-burning study of the primary donor band in Rhodopseudomonas sphaeroides Meech, S. R.; Hoff, A. J.; Wiersma, D. A. Chemical Physics Letters, Vol. 121, Issue 4-5 https://doi.org/10.1016/0009-2614(85)87180-3	journal	November 1985
Simulation of optical spectra from the reaction center of Rb. sphaeroides. Effects of an internal charge-separated state of the special pair Lathrop, Elizabeth J. P.; Friesner, Richard A. The Journal of Physical Chemistry, Vol. 98, Issue 11 https://doi.org/10.1021/j100062a051	journal	March 1994
Ordered and Oriented Supramolecular n/p-Heterojunction Surface Architectures: Completion of the Primary Color Collection Kishore, Ravuri S. K.; Kel, Oksana; Banerji, Natalie Journal of the American Chemical Society, Vol. 131, Issue 31 https://doi.org/10.1021/ja9030648	journal	July 2009
Synthesis and structural characterisation of novel bimetallic dipyrromethene complexes: rotational locking of the 5-aryl group Sutton, Jonathan M.; Rogerson, Eleanor; Wilson, Christopher J. Chemical Communications, Issue 11 https://doi.org/10.1039/b404147j	journal	January 2004
Effect of temperature on symmetry breaking excited state charge separation: restoration of symmetry at elevated temperature Khandelwal, Hitesh; Mallia, Ajith R.; Cheriya, Rijo T. Physical Chemistry Chemical Physics, Vol. 14, Issue 44 https://doi.org/10.1039/c2cp42452e	journal	January 2012
Charge Photogeneration in Organic Solar Cells Clarke, Tracey M.; Durrant, James R. Chemical Reviews, Vol. 110, Issue 11, p. 6736-6767 https://doi.org/10.1021/cr900271s	journal	November 2010
Revisiting the optical signatures of BODIPY with ab initio tools Chibani, Siwar; Le Guennic, Boris; Charaf-Eddin, Azzam Chemical Science, Vol. 4, Issue 5 https://doi.org/10.1039/c3sc22265a	journal	January 2013
Structural Control of the Excited-State Dynamics of Bis(dipyrrinato)zinc Complexes: Self-Assembling Chromophores for Light-Harvesting Architectures Sazanovich, Igor V.; Kirmaier, Christine; Hindin, Eve Journal of the American Chemical Society, Vol. 126, Issue 9 https://doi.org/10.1021/ja038763k	journal	March 2004
Energy Transfer Mechanisms and the Molecular Exciton Model for Molecular Aggregates Kasha, Michael Radiation Research, Vol. 20, Issue 1 https://doi.org/10.2307/3571331	journal	September 1963
Substitution of a Chlorophyll into the Inactive Branch Pheophytin-Binding Site Impairs Charge Separation in Photosystem II Xiong, Ling; Seibert, Michael; Gusev, Alexey V. The Journal of Physical Chemistry B, Vol. 108, Issue 43 https://doi.org/10.1021/jp040262d	journal	October 2004
Structural Interconversion and Regulation of Optical Properties of Stable Hypercoordinate Dipyrrin−Silicon Complexes Sakamoto, Naoya; Ikeda, Chusaku; Yamamura, Masaki Journal of the American Chemical Society, Vol. 133, Issue 13 https://doi.org/10.1021/ja2001924	journal	April 2011
Exciton coupling in coordination compounds Telfer, Shane G.; McLean, Tracey M.; Waterland, Mark R. Dalton Transactions, Vol. 40, Issue 13 https://doi.org/10.1039/c0dt01226b	journal	January 2011
Photochemical Tools for Studying Metal Ion Signaling and Homeostasis Mbatia, Hannah W.; Burdette, Shawn C. Biochemistry, Vol. 51, Issue 37 https://doi.org/10.1021/bi3001769	journal	September 2012
Advances in the Chemistry of Dipyrrins and Their Complexes Wood, Tabitha E.; Thompson, Alison Chemical Reviews, Vol. 107, Issue 5 https://doi.org/10.1021/cr050052c	journal	May 2007
Excited Singlet States of Covalently Bound, Cofacial Dimers and Trimers of Perylene-3,4:9,10-bis(dicarboximide)s Giaimo, Jovan M.; Lockard, Jenny V.; Sinks, Louise E. The Journal of Physical Chemistry A, Vol. 112, Issue 11 https://doi.org/10.1021/jp710847q	journal	March 2008
Solvatochromic Dyes as Solvent Polarity Indicators Reichardt, Christian Chemical Reviews, Vol. 94, Issue 8 https://doi.org/10.1021/cr00032a005	journal	December 1994
Photoinitiated electron collection in polyazine chromophores coupled to water reduction catalysts for solar H2 production Manbeck, Gerald F.; Brewer, Karen J. Coordination Chemistry Reviews, Vol. 257, Issue 9-10 https://doi.org/10.1016/j.ccr.2012.10.019	journal	May 2013
Structural Control of the Photodynamics of Boron−Dipyrrin Complexes Kee, Hooi Ling; Kirmaier, Christine; Yu, Lianhe The Journal of Physical Chemistry B, Vol. 109, Issue 43 https://doi.org/10.1021/jp0525078	journal	November 2005
Symmetry Breaking in the Relaxed S ₁ Excited State of Bianthryl Derivatives in Weakly Polar Solvents Piet, Jacob J.; Schuddeboom, Wouter; Wegewijs, Bastiaan R. Journal of the American Chemical Society, Vol. 123, Issue 22 https://doi.org/10.1021/ja004341o	journal	June 2001
Symmetry-breaking intramolecular charge transfer in the excited state of meso-linked BODIPY dyads Whited, Matthew T.; Patel, Niral M.; Roberts, Sean T. Chem. Commun., Vol. 48, Issue 2 https://doi.org/10.1039/C1CC12260F	journal	January 2012
An Extremely Bright Heteroleptic Bis(dipyrrinato)zinc(II) Complex Kusaka, Shinpei; Sakamoto, Ryota; Kitagawa, Yasutaka Chemistry - An Asian Journal, Vol. 7, Issue 5 https://doi.org/10.1002/asia.201200131	journal	March 2012
Long-lived charge separated states in nanostructured semiconductor photoelectrodes for the production of solar fuels Cowan, Alexander J.; Durrant, James R. Chem. Soc. Rev., Vol. 42, Issue 6 https://doi.org/10.1039/C2CS35305A	journal	January 2013
Towards artificial photosynthesis: Supramolecular, donor–acceptor, porphyrin- and phthalocyanine/carbon nanostructure ensembles Bottari, Giovanni; Trukhina, Olga; Ince, Mine Coordination Chemistry Reviews, Vol. 256, Issue 21-22 https://doi.org/10.1016/j.ccr.2012.03.011	journal	November 2012
From natural to artificial photosynthesis Barber, James; Tran, Phong D. Journal of The Royal Society Interface, Vol. 10, Issue 81 https://doi.org/10.1098/rsif.2012.0984	journal	April 2013
Recent advances in the photocatalytic conversion of carbon dioxide to fuels with water and/or hydrogen using solar energy and beyond Izumi, Yasuo Coordination Chemistry Reviews, Vol. 257, Issue 1 https://doi.org/10.1016/j.ccr.2012.04.018	journal	January 2013
Carotenoids as electron or excited-state energy donors in artificial photosynthesis: an ultrafast investigation of a carotenoporphyrin and a carotenofullerene dyad Pillai, Smitha; Ravensbergen, Janneke; Antoniuk-Pablant, Antaeres Physical Chemistry Chemical Physics, Vol. 15, Issue 13 https://doi.org/10.1039/c3cp50364j	journal	January 2013
Photoinduced Symmetry-Breaking Charge Separation Vauthey, Eric ChemPhysChem, Vol. 13, Issue 8 https://doi.org/10.1002/cphc.201200106	journal	March 2012
Excitonic and Charge Transfer States in Oligomeric 9,10-Anthrylene Chains Fritz, Ralf; Rettig, Wolfgang; Nishiyama, Katsura The Journal of Physical Chemistry A, Vol. 101, Issue 15 https://doi.org/10.1021/jp9639814	journal	April 1997
Dipyrrin Zn^II Complexes with Functional Aryl Groups: Formation, Characterization, and Structures in the Solid State Maeda, Hiromitsu; Hashimoto, Takashi; Fujii, Rika Journal of Nanoscience and Nanotechnology, Vol. 9, Issue 1 https://doi.org/10.1166/jnn.2009.J011	journal	January 2009
Deactivation of 9,9‘-Bianthryl in Solution Studied by Photoacoustic Calorimetry and Fluorescence Schütz, Matthias; Schmidt, Reinhard The Journal of Physical Chemistry, Vol. 100, Issue 6 https://doi.org/10.1021/jp951193t	journal	January 1996
Photoinduced Symmetry-Breaking Charge Separation: The Direction of the Charge Transfer Markovic, Vesna; Villamaina, Diego; Barabanov, Igor Angewandte Chemie International Edition, Vol. 50, Issue 33 https://doi.org/10.1002/anie.201102601	journal	July 2011
Broken Symmetry in Excited States of 9,9′-Bianthryl Rettig, Wolfgang; Zander, Maximilian Berichte der Bunsengesellschaft für physikalische Chemie, Vol. 87, Issue 12 https://doi.org/10.1002/bbpc.19830871212	journal	December 1983
Heteroleptic zinc dipyrromethene complexes Amiri, Asghar; Comeau, Ian M.; Thompson, Alison Journal of Heterocyclic Chemistry, Vol. 43, Issue 2 https://doi.org/10.1002/jhet.5570430225	journal	March 2006
Synthesis and Reversible Control of the Fluorescent Properties of a Divalent Tin Dipyrromethene Kobayashi, Junji; Kushida, Tomokatsu; Kawashima, Takayuki Journal of the American Chemical Society, Vol. 131, Issue 31 https://doi.org/10.1021/ja904470m	journal	July 2009
QM/MM Study of the Role of the Solvent in the Formation of the Charge Separated Excited State in 9,9‘-Bianthryl Grozema, Ferdinand C.; Swart, Marcel; Zijlstra, Robert W. J. Journal of the American Chemical Society, Vol. 127, Issue 31 https://doi.org/10.1021/ja051729g	journal	August 2005
Photocatalytic Water Reduction with Copper-Based Photosensitizers: A Noble-Metal-Free System Luo, Shu-Ping; Mejía, Esteban; Friedrich, Aleksej Angewandte Chemie International Edition, Vol. 52, Issue 1 https://doi.org/10.1002/anie.201205915	journal	October 2012
Cofactor-specific photochemical function resolved by ultrafast spectroscopy in photosynthetic reaction center crystals Huang, L.; Ponomarenko, N.; Wiederrecht, G. P. Proceedings of the National Academy of Sciences, Vol. 109, Issue 13 https://doi.org/10.1073/pnas.1116862109	journal	March 2012
Selective and sensitive “turn-on” fluorescent Zn ²⁺ sensors based on di- and tripyrrins with readily modulated emission wavelengths Ding, Yubin; Xie, Yongshu; Li, Xin Chemical Communications, Vol. 47, Issue 19 https://doi.org/10.1039/C1CC11493J	journal	January 2011
Structural Changes Accompanying Intramolecular Electron Transfer: Focus on Twisted Intramolecular Charge-Transfer States and Structures Grabowski, Zbigniew R.; Rotkiewicz, Krystyna; Rettig, Wolfgang Chemical Reviews, Vol. 103, Issue 10 https://doi.org/10.1021/cr940745l	journal	October 2003
Small-Molecule Fluorescent Sensors for Investigating Zinc Metalloneurochemistry Nolan, Elizabeth M.; Lippard, Stephen J. Accounts of Chemical Research, Vol. 42, Issue 1 https://doi.org/10.1021/ar8001409	journal	January 2009
π-Extended Dipyrrins Capable of Highly Fluorogenic Complexation with Metal Ions Filatov, Mikhail A.; Lebedev, Artem Y.; Mukhin, Sergei N. Journal of the American Chemical Society, Vol. 132, Issue 28 https://doi.org/10.1021/ja102852v	journal	July 2010
Fluorescence studies on solvent-induced intramolecular charge separation in symmetric biaryls Zander, Maximilian; Rettig, Wolfgang Chemical Physics Letters, Vol. 110, Issue 6 https://doi.org/10.1016/0009-2614(84)85471-8	journal	October 1984
Magnitude and direction of the change in dipole moment associated with excitation of the primary electron donor in Rhodopseudomonas sphaeroides reaction centers Lockhart, David J.; Boxer, Steven G. Biochemistry, Vol. 26, Issue 3 https://doi.org/10.1021/bi00377a001	journal	February 1987
Luminescent Dipyrrinato Complexes of Trivalent Group 13 Metal Ions Thoi, Van S.; Stork, Jay R.; Magde, Douglas Inorganic Chemistry, Vol. 45, Issue 26 https://doi.org/10.1021/ic061581h	journal	December 2006

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