Evidence for Interfacial Halogen Bonding

Swords, Wesley B.; Simon, Sarah J. C.; Parlane, Fraser G. L.; Dean, Rebecca K.; Kellett, Cameron W.; Hu, Ke; Meyer, Gerald J.; Berlinguette, Curtis P.

doi:10.1002/anie.201510641

Title: Evidence for Interfacial Halogen Bonding

Journal Article · Fri Apr 08 00:00:00 EDT 2016 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201510641· OSTI ID:1400961

Swords, Wesley B. ^[1]; Simon, Sarah J. C. ^[2]; Parlane, Fraser G. L. ^[2]; Dean, Rebecca K. ^[2]; Kellett, Cameron W. ^[2]; Hu, Ke ^[1]; Meyer, Gerald J. ^[1]; Berlinguette, Curtis P. ^[2]

Department of Chemistry The University of North Carolina at Chapel Hill Murray Hall 2202B Chapel Hill NC 27599-3290 USA
Departments of Chemistry and Chemical &, Biological Engineering The University of British Columbia 2036 Main Mall Vancouver BC V6T1Z1 Canada

Abstract A homologous series of donor–π–acceptor dyes was synthesized, differing only in the identity of the halogen substituents about the triphenylamine (TPA; donor) portion of each molecule. Each Dye‐X (X=F, Cl, Br, and I) was immobilized on a TiO ₂ surface to investigate how the halogen substituents affect the reaction between the light‐induced charge‐separated state, TiO ₂ (e ⁻ )/ Dye‐X ⁺ , with iodide in solution. Transient absorption spectroscopy showed progressively faster reactivity towards nucleophilic iodide with more polarizable halogen substituents: Dye‐F < Dye‐Cl < Dye‐Br < Dye‐I . Given that all other structural and electronic properties for the series are held at parity, with the exception of an increasingly larger electropositive σ‐hole on the heavier halogens, the differences in dye regeneration kinetics for Dye‐Cl , Dye‐Br , and Dye‐I are ascribed to the extent of halogen bonding with the nucleophilic solution species.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0013461

OSTI ID:: 1400961

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Vol. 55 Journal Issue: 20; ISSN 1433-7851

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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Cited by: 34 works

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References (46)

Cationic Multidentate Halogen-Bond Donors in Halide Abstraction Organocatalysis: Catalyst Optimization by Preorganization Jungbauer, Stefan H.; Huber, Stefan M. Journal of the American Chemical Society, Vol. 137, Issue 37 https://doi.org/10.1021/jacs.5b07863	journal	September 2015
Femtosecond Absorption Spectroscopy of Transition Metal Charge-Transfer Complexes McCusker, James K. Accounts of Chemical Research, Vol. 36, Issue 12 https://doi.org/10.1021/ar030111d	journal	December 2003
Halogen bond-assisted electron transfer reactions of aliphatic bromosubstituted electrophiles Rosokha, Sergiy V.; Vinakos, Michael K. Phys. Chem. Chem. Phys., Vol. 16, Issue 5 https://doi.org/10.1039/C3CP54004A	journal	January 2014
Halogen Bonding: A Supramolecular Entry for Assembling Nanoparticles Shirman, Tanya; Arad, Talmon; van der Boom, Milko E. Angewandte Chemie International Edition, Vol. 49, Issue 5 https://doi.org/10.1002/anie.200905984	journal	December 2009
Dye Regeneration Kinetics in Dye-Sensitized Solar Cells Daeneke, Torben; Mozer, Attila J.; Uemura, Yu Journal of the American Chemical Society, Vol. 134, Issue 41 https://doi.org/10.1021/ja3054578	journal	October 2012
Oxidation of thiocyanate and iodide by iridium(IV) Stanbury, David M.; Wilmarth, Wayne K.; Khalaf, Shada Inorganic Chemistry, Vol. 19, Issue 9 https://doi.org/10.1021/ic50211a046	journal	September 1980
Photodriven heterogeneous charge transfer with transition-metal compounds anchored to TiO ₂ semiconductor surfaces Ardo, Shane; Meyer, Gerald J. Chem. Soc. Rev., Vol. 38, Issue 1 https://doi.org/10.1039/B804321N	journal	January 2009
Halogen-Bonding Mediated Stepwise Assembly of Gold Nanoparticles onto Planar Surfaces Shirman, Tanya; Kaminker, Revital; Freeman, Dalia ACS Nano, Vol. 5, Issue 8 https://doi.org/10.1021/nn201923q	journal	August 2011
Non-symmetrical dielectric relaxation behaviour arising from a simple empirical decay function Williams, Graham; Watts, David C. Transactions of the Faraday Society, Vol. 66 https://doi.org/10.1039/tf9706600080	journal	January 1970
Atomic Level Resolution of Dye Regeneration in the Dye-Sensitized Solar Cell Robson, Kiyoshi C. D.; Hu, Ke; Meyer, Gerald J. Journal of the American Chemical Society, Vol. 135, Issue 5 https://doi.org/10.1021/ja311640f	journal	January 2013
Dye-Sensitized Solar Cells Hagfeldt, Anders; Boschloo, Gerrit; Sun, Licheng Chemical Reviews, Vol. 110, Issue 11 https://doi.org/10.1021/cr900356p	journal	November 2010
Halogen-bonding-triggered supramolecular gel formation Meazza, Lorenzo; Foster, Jonathan A.; Fucke, Katharina Nature Chemistry, Vol. 5, Issue 1 https://doi.org/10.1038/nchem.1496	journal	November 2012
The One-Electron Outer-Sphere Oxidation of Iodide and of Thiocyanide Ions by Transition Metal Complexes: Linear Free-Energy Relationships Nord, Gwyneth Comments on Inorganic Chemistry, Vol. 13, Issue 3-4 https://doi.org/10.1080/02603599208052196	journal	January 1992
Halogen Bonding: A Paradigm in Supramolecular Chemistry Metrangolo, Pierangelo; Resnati, Giuseppe Chemistry - A European Journal, Vol. 7, Issue 12 https://doi.org/10.1002/1521-3765(20010618)7:12<2511::AID-CHEM25110>3.0.CO;2-T	journal	June 2001
Detailed comparison of the Williams–Watts and Cole–Davidson functions Lindsey, C. P.; Patterson, G. D. The Journal of Chemical Physics, Vol. 73, Issue 7 https://doi.org/10.1063/1.440530	journal	October 1980
A Tridentate Halogen-Bonding Receptor for Tight Binding of Halide Anions Sarwar, Mohammed G.; Dragisic, Bojan; Sagoo, Sandeep Angewandte Chemie, Vol. 122, Issue 9 https://doi.org/10.1002/ange.200906488	journal	January 2010
Halogen bonding in solution: thermodynamics and applications Beale, Thomas M.; Chudzinski, Michael G.; Sarwar, Mohammed G. Chem. Soc. Rev., Vol. 42, Issue 4 https://doi.org/10.1039/C2CS35213C	journal	January 2013
Interfacial halogen bonding probed using force spectroscopy Boterashvili, Meital; Shirman, Tanya; Cohen, Sidney R. Chemical Communications, Vol. 49, Issue 34 https://doi.org/10.1039/c3cc40378e	journal	January 2013
An overview of halogen bonding Politzer, Peter; Lane, Pat; Concha, Monica C. Journal of Molecular Modeling, Vol. 13, Issue 2 https://doi.org/10.1007/s00894-006-0154-7	journal	September 2006
Quantifying Regeneration in Dye-Sensitized Solar Cells Anderson, Assaf Y.; Barnes, Piers R. F.; Durrant, James R. The Journal of Physical Chemistry C, Vol. 115, Issue 5 https://doi.org/10.1021/jp1101048	journal	December 2010
Solution-Phase Self-Assembly of Complementary Halogen Bonding Polymers Vanderkooy, Alan; Taylor, Mark S. Journal of the American Chemical Society, Vol. 137, Issue 15 https://doi.org/10.1021/jacs.5b00754	journal	April 2015
Halogen bonding: the σ-hole: Proceedings of “Modeling interactions in biomolecules II”, Prague, September 5th–9th, 2005 Clark, Timothy; Hennemann, Matthias; Murray, Jane S. Journal of Molecular Modeling, Vol. 13, Issue 2 https://doi.org/10.1007/s00894-006-0130-2	journal	August 2006
CHEMISTRY: Halogen Versus Hydrogen Metrangolo, P.; Resnati, G. Science, Vol. 321, Issue 5891 https://doi.org/10.1126/science.1162215	journal	August 2008
Structural Aspects of Interatomic Charge-Transfer Bonding Hassel, O. Science, Vol. 170, Issue 3957 https://doi.org/10.1126/science.170.3957.497	journal	October 1970
Expanded Halogen-Bonded Anion Organic Networks with Star-Shaped Iodoethynyl-Substituted Molecules: From Corrugated 2D Hexagonal Lattices to Pyrite-Type 2-Fold Interpenetrated Cubic Lattices Lieffrig, Julien; Jeannin, Olivier; Fourmigué, Marc Journal of the American Chemical Society, Vol. 135, Issue 16 https://doi.org/10.1021/ja400740v	journal	April 2013
Interfacial Charge Recombination Between e ⁻ −TiO ₂ and the I ⁻ /I ₃ ⁻ Electrolyte in Ruthenium Heteroleptic Complexes: Dye Molecular Structure−Open Circuit Voltage Relationship Reynal, Anna; Forneli, Amparo; Martinez-Ferrero, Eugenia Journal of the American Chemical Society, Vol. 130, Issue 41 https://doi.org/10.1021/ja800513m	journal	October 2008
Evidence for Halogen Bond Covalency in Acyclic and Interlocked Halogen-Bonding Receptor Anion Recognition Robinson, Sean W.; Mustoe, Chantal L.; White, Nicholas G. Journal of the American Chemical Society, Vol. 137, Issue 1 https://doi.org/10.1021/ja511648d	journal	December 2014
Halogen Bonding Based Recognition Processes: A World Parallel to Hydrogen Bonding ^† Metrangolo, Pierangelo; Neukirch, Hannes; Pilati, Tullio Accounts of Chemical Research, Vol. 38, Issue 5 https://doi.org/10.1021/ar0400995	journal	May 2005
A Tridentate Halogen-Bonding Receptor for Tight Binding of Halide Anions Sarwar, Mohammed G.; Dragisic, Bojan; Sagoo, Sandeep Angewandte Chemie International Edition, Vol. 49, Issue 9 https://doi.org/10.1002/anie.200906488	journal	January 2010
Energy levels, charge injection, charge recombination and dye regeneration dynamics for donor–acceptor π-conjugated organic dyes in mesoscopic TiO2 sensitized solar cells Planells, Miquel; Pellejà, Laia; Clifford, John N. Energy & Environmental Science, Vol. 4, Issue 5 https://doi.org/10.1039/c1ee01060c	journal	January 2011
A Nuclear Isotope Effect for Interfacial Electron Transfer: Excited-State Electron Injection from Ru Ammine Compounds to Nanocrystalline TiO ₂ Liu, Feng; Meyer, Gerald J. Journal of the American Chemical Society, Vol. 127, Issue 3 https://doi.org/10.1021/ja045266a	journal	January 2005
Engineering Organic Sensitizers for Iodine-Free Dye-Sensitized Solar Cells: Red-Shifted Current Response Concomitant with Attenuated Charge Recombination Bai, Yu; Zhang, Jing; Zhou, Difei Journal of the American Chemical Society, Vol. 133, Issue 30 https://doi.org/10.1021/ja203708k	journal	August 2011
Halogen Bonding in Crystal Engineering Metrangolo, Pierangelo; Resnati, Giuseppe; Pilati, Tullio Halogen Bonding https://doi.org/10.1007/430_2007_060	book	January 2007
The Nature of -Cl.cntdot..cntdot..cntdot.Cl- Intermolecular Interactions Price, S. L.; Stone, A. J.; Lucas, J. Journal of the American Chemical Society, Vol. 116, Issue 11 https://doi.org/10.1021/ja00090a041	journal	June 1994
A Halogen-Bonding Catenane for Anion Recognition and Sensing Caballero, Antonio; Zapata, Fabiola; White, Nicholas G. Angewandte Chemie International Edition, Vol. 51, Issue 8 https://doi.org/10.1002/anie.201108404	journal	January 2012
A Halogen-Bonding Catenane for Anion Recognition and Sensing Caballero, Antonio; Zapata, Fabiola; White, Nicholas G. Angewandte Chemie, Vol. 124, Issue 8 https://doi.org/10.1002/ange.201108404	journal	January 2012
Iodide Chemistry in Dye-Sensitized Solar Cells: Making and Breaking I−I Bonds for Solar Energy Conversion Rowley, John G.; Farnum, Byron H.; Ardo, Shane The Journal of Physical Chemistry Letters, Vol. 1, Issue 20 https://doi.org/10.1021/jz101311d	journal	October 2010
Halogen bonding in solution Erdélyi, Máté Chemical Society Reviews, Vol. 41, Issue 9 https://doi.org/10.1039/c2cs15292d	journal	January 2012
Structure/Function Relationships in Dyes for Solar Energy Conversion: A Two-Atom Change in Dye Structure and the Mechanism for Its Effect on Cell Voltage O’Regan, Brian C.; Walley, Kate; Juozapavicius, Mindaugas Journal of the American Chemical Society, Vol. 131, Issue 10 https://doi.org/10.1021/ja806869x	journal	March 2009
Halogen Bonding with Dihalogens and Interhalogens Pennington, William T.; Hanks, Timothy W.; Arman, Hadi D. Halogen Bonding https://doi.org/10.1007/430_2007_067	book	January 2007
Properties of atoms in molecules: atomic volumes Bader, Richard F. W.; Carroll, Marshall T.; Cheeseman, James R. Journal of the American Chemical Society, Vol. 109, Issue 26 https://doi.org/10.1021/ja00260a006	journal	December 1987
Halogen Bonding: A Supramolecular Entry for Assembling Nanoparticles Shirman, Tanya; Arad, Talmon; van der Boom, Milko E. Angewandte Chemie, Vol. 122, Issue 5 https://doi.org/10.1002/ange.200905984	journal	January 2010
Halogen bonding in water results in enhanced anion recognition in acyclic and rotaxane hosts Langton, Matthew J.; Robinson, Sean W.; Marques, Igor Nature Chemistry, Vol. 6, Issue 12 https://doi.org/10.1038/nchem.2111	journal	November 2014
Halogen bonding: an electrostatically-driven highly directional noncovalent interaction Politzer, Peter; Murray, Jane S.; Clark, Timothy Physical Chemistry Chemical Physics, Vol. 12, Issue 28 https://doi.org/10.1039/c004189k	journal	January 2010
Formation of Halogen Bond-Based 2D Supramolecular Assemblies by Electric Manipulation Zheng, Qing-Na; Liu, Xuan-He; Chen, Ting Journal of the American Chemical Society, Vol. 137, Issue 19 https://doi.org/10.1021/jacs.5b02206	journal	May 2015
Symmetric Halogen Bonding Is Preferred in Solution Carlsson, Anna-Carin C.; Gräfenstein, Jürgen; Budnjo, Adnan Journal of the American Chemical Society, Vol. 134, Issue 12 https://doi.org/10.1021/ja301341h	journal	March 2012

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