Discovery of Unusually Stable Reduced Viologen via Synergistic Folding and Encapsulation

MacInnes, Molly M.; Cousineau, Benjamin R.; Youngs, Sarah M.; Sinniah, Kumar; Reczek, Joseph J.; Maldonado, Stephen

doi:10.1149/2.0711915jes

Discovery of Unusually Stable Reduced Viologen via Synergistic Folding and Encapsulation

Journal Article · 01 January 2019 · Journal of the Electrochemical Society

DOI:https://doi.org/10.1149/2.0711915jes· OSTI ID:1801703

; Cousineau, Benjamin R.; Youngs, Sarah M.; Sinniah, Kumar; Reczek, Joseph J.;

Not provided.

Research Organization:: Univ. of Michigan, Ann Arbor, MI (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0006628

OSTI ID:: 1801703

Journal Information:: Journal of the Electrochemical Society, Vol. 166, Issue 15; ISSN 0013-4651

Publisher:: IOP Publishing - The Electrochemical Society

Country of Publication:: United States

Language:: English

References (69)

Electrochemistry of the viologens Bird, C. L.; Kuhn, A. T. Chemical Society Reviews, Vol. 10, Issue 1 https://doi.org/10.1039/cs9811000049	journal	January 1981
A [2]Pseudorotaxane-Based Molecular Machine: Reversible Formation of a Molecular Loop Driven by Electrochemical and Photochemical Stimuli Jeon, Woo Sung; Ziganshina, Albina Y.; Lee, Jae Wook Angewandte Chemie, Vol. 115, Issue 34, p. 4231-4234 https://doi.org/10.1002/ange.200351925	journal	September 2003
The synthesis of a rigid conjugated viologen and its cucurbituril pseudorotaxanes Song, Yingfeng; Huang, Xinghua; Hua, Haojie Dyes and Pigments, Vol. 137 https://doi.org/10.1016/j.dyepig.2016.10.012	journal	February 2017
Viologen-Based Rotaxanes from Dibenzo-30-crown-10 Wessels, Hanlie R.; Slebodnick, Carla; Gibson, Harry W. Journal of the American Chemical Society, Vol. 140, Issue 23 https://doi.org/10.1021/jacs.8b04477	journal	May 2018
Toxicity of Redox Cycling Pesticides in Primary Mesencephalic Cultures Bonneh-Barkay, Dafna; Langston, William J.; Di Monte, Donato A. Antioxidants & Redox Signaling, Vol. 7, Issue 5-6 https://doi.org/10.1089/ars.2005.7.649	journal	May 2005
Determination of quaternary ammonium pesticides by liquid chromatography–electrospray tandem mass spectrometry Castro, R.; Moyano, E.; Galceran, M. T. Journal of Chromatography A, Vol. 914, Issue 1-2 https://doi.org/10.1016/S0021-9673(01)00523-4	journal	April 2001
Introduction Maroni, M.; Colosio, C.; Ferioli, A. Toxicology, Vol. 143, Issue 1 https://doi.org/10.1016/S0300-483X(99)00152-3	journal	February 2000
A Total Organic Aqueous Redox Flow Battery Employing a Low Cost and Sustainable Methyl Viologen Anolyte and 4-HO-TEMPO Catholyte Liu, Tianbiao; Wei, Xiaoliang; Nie, Zimin Advanced Energy Materials, Vol. 6, Issue 3, 1501449 https://doi.org/10.1002/aenm.201501449	journal	December 2015
Viologens as Charge Carriers in a Polymer-Based Battery Anode Sen, Sujat; Saraidaridis, James; Kim, Sung Yeol ACS Applied Materials & Interfaces, Vol. 5, Issue 16, p. 7825-7830 https://doi.org/10.1021/am401590q	journal	July 2013
Impact of Redox-Active Polymer Molecular Weight on the Electrochemical Properties and Transport Across Porous Separators in Nonaqueous Solvents Nagarjuna, Gavvalapalli; Hui, Jingshu; Cheng, Kevin J. Journal of the American Chemical Society, Vol. 136, Issue 46, p. 16309-16316 https://doi.org/10.1021/ja508482e	journal	October 2014
Impact of Backbone Tether Length and Structure on the Electrochemical Performance of Viologen Redox Active Polymers Burgess, Mark; Chénard, Etienne; Hernández-Burgos, Kenneth Chemistry of Materials, Vol. 28, Issue 20 https://doi.org/10.1021/acs.chemmater.6b02825	journal	October 2016
An Approach Toward Replacing Vanadium: A Single Organic Molecule for the Anode and Cathode of an Aqueous Redox-Flow Battery Janoschka, Tobias; Friebe, Christian; Hager, Martin D. ChemistryOpen, Vol. 6, Issue 2 https://doi.org/10.1002/open.201600155	journal	February 2017
Organic electrochromic materials Mortimer, Roger J. Electrochimica Acta, Vol. 44, Issue 18 https://doi.org/10.1016/S0013-4686(99)00046-8	journal	May 1999
Electrochromic Materials Mortimer, Roger J. Annual Review of Materials Research, Vol. 41, Issue 1 https://doi.org/10.1146/annurev-matsci-062910-100344	journal	August 2011
Electrochromic Polymers Covalently Anchored to Electrode Surfaces. Optical and Electrochemical Properties of a Viologen‐Based Polymer Bookbinder, Dana C.; Wrighton, Mark S. Journal of The Electrochemical Society, Vol. 130, Issue 5 https://doi.org/10.1149/1.2119888	journal	May 1983
A convenient electrochemical preparation of reduced methyl viologen and a kinetic study of the reaction with oxygen using an anaerobic stopped-flow apparatus Thorneley, Roger N. F. Biochimica et Biophysica Acta (BBA) - Bioenergetics, Vol. 333, Issue 3 https://doi.org/10.1016/0005-2728(74)90133-9	journal	March 1974
The coulometric determination of oxygen with the electrolytically generated viologen radical-cation Leest, R. E. V. D. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 43, Issue 2 https://doi.org/10.1016/S0022-0728(73)80495-4	journal	April 1973
Bipyridylium quaternary salts and related compounds. Part 6.—Pulse radiolysis studies of the reaction of paraquat radical analogues with oxygen Farrington, John A.; Ebert, Michael; Land, Edward J. Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, Vol. 74, Issue 0 https://doi.org/10.1039/f19787400665	journal	January 1978
Partition Parameters for Three Redox Forms of Viologen in a Nonionic Micellar Solution Hoshino, Katsuyoshi; Sasaki, Hiroaki; Suga, Kosaku Bulletin of the Chemical Society of Japan, Vol. 60, Issue 4 https://doi.org/10.1246/bcsj.60.1521	journal	April 1987
Micellar effects on the reductive electrochemistry of methylviologen Kaifer, Angel E.; Bard, Allen J. The Journal of Physical Chemistry, Vol. 89, Issue 22 https://doi.org/10.1021/j100268a044	journal	October 1985
Inclusion of methylviologen in cucurbit[7]uril Kim, H. -J.; Jeon, W. S.; Ko, Y. H. Proceedings of the National Academy of Sciences, Vol. 99, Issue 8 https://doi.org/10.1073/pnas.062656699	journal	March 2002
Control of the stoichiometry in host–guest complexation by redox chemistry of guests: Inclusion of methylviologen in cucurbit[8]uril Jeon, Woo Sung; Kim, Hee-Joon; Lee, Chongmok Chem. Commun., Issue 17 https://doi.org/10.1039/B202082C	journal	January 2002
Electrochemical properties of an amphiphilic viologen in differently charged micelles Kostela, J.; Elmgren, M.; Hansson, P. Journal of Electroanalytical Chemistry, Vol. 536, Issue 1-2 https://doi.org/10.1016/S0022-0728(02)01208-1	journal	November 2002
Sulfonatocalix[8]arene as a Potential Reaction Cavity: Photo- and Electro-active Dicationic Guests Arrest Conformational Equilibrium Kaliappan, Raja; Ling, Yonghua; Kaifer, Angel E. Langmuir, Vol. 25, Issue 16 https://doi.org/10.1021/la900659r	journal	April 2009
Reduction potentials of N-hexadecyl-N'-methyl viologen(2+/+) solubilized in cationic, nonionic, and anionic micelles Lee, Chi Woo; Oh, Mi Kyung; Jang, Jai Man Langmuir, Vol. 9, Issue 7 https://doi.org/10.1021/la00031a051	journal	July 1993
Cucurbiturils as Versatile Receptors for Redox Active Substrates Kaifer, Angel E.; Li, Wei; Yi, Song Israel Journal of Chemistry, Vol. 51, Issue 5-6 https://doi.org/10.1002/ijch.201100042	journal	May 2011
Electrocatalytic reduction of oxygen by cation radicals of methyl viologen or diquat complexes with macrocyclic crown ethers Pospíšil, L.; Fuoco, R.; Papoff, P. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 256, Issue 1 https://doi.org/10.1016/0022-0728(88)85009-5	journal	November 1988
Viologen homopolymer, polymer mixture and polymer bilayer films on electrodes Willman, K. W.; Murray, Royce W. Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 133, Issue 2 https://doi.org/10.1016/0368-1874(82)85139-3	journal	February 1982
Redox-Sensitive Microporous Membranes Prepared from Poly(vinylidene fluoride) Grafted with Viologen-Containing Polymer Side Chains Liu, X.; Neoh, K. G.; Kang, E. T. Macromolecules, Vol. 36, Issue 22 https://doi.org/10.1021/ma034794o	journal	November 2003
Polymer Films on Electrodes: XXVII . Electrochemical and Ellipsometric Measurements of a Viologen‐Siloxane Polymer Film: Deposition, Solvent Swelling, Oxidation‐State‐Dependent Thickness, and Charge Transport Kepley, Larry J.; Bard, Allen J. Journal of The Electrochemical Society, Vol. 142, Issue 12 https://doi.org/10.1149/1.2048475	journal	December 1995
Electrochemical stimulus-responsive supramolecular polymer based on sulfonatocalixarene and viologen dimers Guo, Dong-Sheng; Chen, Si; Qian, Hai Chemical Communications, Vol. 46, Issue 15 https://doi.org/10.1039/b925157j	journal	January 2010
Electrochromic organic and polymeric materials for display applications Mortimer, Roger J.; Dyer, Aubrey L.; Reynolds, John R. Displays, Vol. 27, Issue 1 https://doi.org/10.1016/j.displa.2005.03.003	journal	January 2006
Fast electron storage with colloidal semiconductors functionalized with polymeric viologen Nakahira, Takayuki; Graetzel, Michael The Journal of Physical Chemistry, Vol. 88, Issue 18 https://doi.org/10.1021/j150662a029	journal	August 1984
Polymer effect in electrochromic behavior of oligomeric viologens Sato, Hirotsugu; Tamamura, Toshiaki Journal of Applied Polymer Science, Vol. 24, Issue 10 https://doi.org/10.1002/app.1979.070241001	journal	November 1979
Charge-transfer reactions in pendant viologen polymers coated on graphite electrodes and at electrode/pendant viologen polymer film interfaces Oyama, Noboru; Ohsaka, Takeo; Yamamoto, Hisao The Journal of Physical Chemistry, Vol. 90, Issue 16 https://doi.org/10.1021/j100407a065	journal	July 1986
Viologen(2+/1+) and viologen(1+/0) electron-self-exchange reactions in a redox polymer Dalton, E. F.; Murray, Royce W. The Journal of Physical Chemistry, Vol. 95, Issue 16 https://doi.org/10.1021/j100169a056	journal	August 1991
Polyviologens – a novel class of cationic polyelectrolyte redox polymers Factor, A.; Heinsohn, G. E. Journal of Polymer Science Part B: Polymer Letters, Vol. 9, Issue 4 https://doi.org/10.1002/pol.1971.110090408	journal	April 1971
Inclusion, Solubilization, and Stabilization of Two-Electron Reduced Species of Methyl Viologen by Cyclodextrins Matsue, Tomokazu; Kato, Tetsuya; Akiba, Uichi Chemistry Letters, Vol. 14, Issue 12 https://doi.org/10.1246/cl.1985.1825	journal	December 1985
Electrochromic properties of alkylviologen-cyclodextrin systems Yasuda, A.; Mori, H.; Seto, J. Journal of Applied Electrochemistry, Vol. 17, Issue 3 https://doi.org/10.1007/BF01084131	journal	May 1987
Electrochemistry of viologens at polypyrrole doped with sulfonated β–cyclodextrin Annibaldi, Valeria; Breslin, Carmel B. Journal of Electroanalytical Chemistry, Vol. 832 https://doi.org/10.1016/j.jelechem.2018.11.025	journal	January 2019
Cucurbit[7]uril: A Very Effective Host for Viologens and Their Cation Radicals Ong, Winston; Gómez-Kaifer, Marielle; Kaifer, Angel E. Organic Letters, Vol. 4, Issue 10 https://doi.org/10.1021/ol025869w	journal	May 2002
Host−Guest Chemistry and Light Driven Molecular Lock of Ru(bpy) ₃ −Viologen with Cucurbit[7−8]urils Sun, Shiguo; Zhang, Rong; Andersson, Samir The Journal of Physical Chemistry B, Vol. 111, Issue 47 https://doi.org/10.1021/jp074582j	journal	November 2007
A Noncovalently Reversible Paramagnetic Switch in Water Buck, Alexander T.; Paletta, Joseph T.; Khindurangala, Shalika A. Journal of the American Chemical Society, Vol. 135, Issue 29 https://doi.org/10.1021/ja403505z	journal	July 2013
Solvation spectra. Part 17.—Water-induced dimerization of various dye and related paramagnetic ions studied by optical and electron spin resonance spectroscopy Blandamer, M. J.; Brivati, J. A.; Fox, M. F. Trans. Faraday Soc., Vol. 63, Issue 0 https://doi.org/10.1039/tf9676301850	journal	January 1967
Intramolecular association of covalently linked viologen radicals Neta, Pedatsur; Richoux, Marie-Claude; Harriman, Anthony Journal of the Chemical Society, Faraday Transactions 2, Vol. 81, Issue 9 https://doi.org/10.1039/f29858101427	journal	January 1985
Stable (Long-Bonded) Dimers via the Quantitative Self-Association of Different Cationic, Anionic, and Uncharged π-Radicals: Structures, Energetics, and Optical Transitions Lü, Jian-Ming; Rosokha, Sergiy V.; Kochi, Jay K. Journal of the American Chemical Society, Vol. 125, Issue 40 https://doi.org/10.1021/ja0364928	journal	October 2003
The Viologen Cation Radical Pimer: A Case of Dispersion-Driven Bonding Geraskina, Margarita R.; Dutton, Andrew S.; Juetten, Mark J. Angewandte Chemie, Vol. 129, Issue 32 https://doi.org/10.1002/ange.201704959	journal	July 2017
Determination of E20-E10 in multistep charge transfer by stationary-electrode pulse and cyclic voltammetry: application to binuclear ruthenium ammines Richardson, David E.; Taube, Henry. Inorganic Chemistry, Vol. 20, Issue 4 https://doi.org/10.1021/ic50218a062	journal	April 1981
Photoreduction of Bisviologen Compounds, Viologen–(CH ₂ ) _n –Viologen, by 2-Propanol Furue, Masaoki; Nozakura, Shun-ichi Bulletin of the Chemical Society of Japan, Vol. 55, Issue 2 https://doi.org/10.1246/bcsj.55.513	journal	February 1982
Binding of viologen derivatives to cucurbit[8]uril Peerannawar, Swarada R.; Gobre, Vivekanand V.; Gejji, Shridhar P. Computational and Theoretical Chemistry, Vol. 983 https://doi.org/10.1016/j.comptc.2011.12.013	journal	March 2012
Semi-Empirical Calculations on the Optical Absorption of Methylviologen and p-Cyanophenylviologen in Different Oxidation States Mizuguchi, Jin; Karfunkel, Heinrich Berichte der Bunsengesellschaft für physikalische Chemie, Vol. 97, Issue 11 https://doi.org/10.1002/bbpc.19930971108	journal	November 1993
UV-vis-NIR and Raman spectroelectrochemical studies on viologen cation radicals: evidence for the presence of various types of aggregate species Lee, Chongmok; Lee, Young Mi; Moon, Myung Sun Journal of Electroanalytical Chemistry, Vol. 416, Issue 1-2 https://doi.org/10.1016/S0022-0728(96)04741-9	journal	November 1996
Dimerization of Conjugated Radical Cations: An Emerging Non-Covalent Interaction for Self-Assembly Zhang, Dan-Wei; Tian, Jia; Chen, Lan Chemistry - An Asian Journal, Vol. 10, Issue 1 https://doi.org/10.1002/asia.201402805	journal	September 2014
Intermolecular Covalent π−π Bonding Interaction Indicated by Bond Distances, Energy Bands, and Magnetism in Biphenalenyl Biradicaloid Molecular Crystal Huang, Jingsong; Kertesz, Miklos Journal of the American Chemical Society, Vol. 129, Issue 6 https://doi.org/10.1021/ja066426g	journal	February 2007
A Stable Neutral Hydrocarbon Radical: Synthesis, Crystal Structure, and Physical Properties of 2,5,8-Tri- tert -butyl-phenalenyl Goto, Kosaburo; Kubo, Takashi; Yamamoto, Kagetoshi Journal of the American Chemical Society, Vol. 121, Issue 7 https://doi.org/10.1021/ja9836242	journal	February 1999
Electronic structure of a stable phenalenyl radical in crystalline state as studied by SQUID measurements, cw-ESR, and 13C CP/MAS NMR spectroscopy Fukui, K.; Sato, K.; Shiomi, D. Synthetic Metals, Vol. 103, Issue 1-3 https://doi.org/10.1016/S0379-6779(98)00396-8	journal	June 1999
Stable Free Radicals. II. The Reduction of 1-Methyl-4-cyanopyridinium Ion to Methylviologen Cation Radical Kosower, Edward M.; Cotter, John L. Journal of the American Chemical Society, Vol. 86, Issue 24 https://doi.org/10.1021/ja01078a026	journal	December 1964
Reversible Dimerization and Polymerization of a Janus Diradical To Produce Labile C−C Bonds and Large Chromic Effects Zafra, José L.; Qiu, Lili; Yanai, Naoyuki Angewandte Chemie International Edition, Vol. 55, Issue 47 https://doi.org/10.1002/anie.201605997	journal	October 2016
Pancake bonds: π-Stacked dimers of organic and light-atom radicals Preuss, Kathryn E. Polyhedron, Vol. 79 https://doi.org/10.1016/j.poly.2014.04.005	journal	September 2014
π-Dimers and π-Stacks in Solution and in Conducting Polymers Miller, Larry L.; Mann, Kent R. Accounts of Chemical Research, Vol. 29, Issue 9 https://doi.org/10.1021/ar9600446	journal	January 1996
Pancake Bonding: An Unusual Pi-Stacking Interaction Kertesz, Miklos Chemistry - A European Journal, Vol. 25, Issue 2 https://doi.org/10.1002/chem.201802385	journal	November 2018
Cyclobis(paraquat-p-phenylene). A Tetracationic Multipurpose Receptor Odell, Barbara; Reddington, Mark V.; Slawin, Alexandra M. Z. Angewandte Chemie International Edition in English, Vol. 27, Issue 11, p. 1547-1550 https://doi.org/10.1002/anie.198815471	journal	November 1988
Radically enhanced molecular recognition Trabolsi, Ali; Khashab, Niveen; Fahrenbach, Albert C. Nature Chemistry, Vol. 2, Issue 1 https://doi.org/10.1038/nchem.479	journal	December 2009
A [2]Catenane-Based Solid State Electronically Reconfigurable Switch Collier, C. P. Science, Vol. 289, Issue 5482 https://doi.org/10.1126/science.289.5482.1172	journal	August 2000
Single and double bridged viologenes and intramolecular pimerization of their cation radicals Geuder, Wolfram; Hünig, Siegfried; Suchy, Adolf Tetrahedron, Vol. 42, Issue 6, p. 1665-1677 https://doi.org/10.1016/S0040-4020(01)87583-9	journal	January 1986
Phane mit zwei 4,4′-Bipyridiniumeinheiten - eine neue Verbindungsklasse Geuder, Wolfram; Hünig, Siegfried; Suchy, Adolf Angewandte Chemie, Vol. 95, Issue 6 https://doi.org/10.1002/ange.19830950613	journal	June 1983
Light-induced electron transfer in colloidal semiconductor dispersions: single vs. dielectronic reduction of acceptors by conduction-band electrons Moser, Jacques; Graetzel, Michael Journal of the American Chemical Society, Vol. 105, Issue 22 https://doi.org/10.1021/ja00360a003	journal	October 1983
Photochromism of double-bridged viologens in a polar polymer matrix Sun, Xuehui; Yang, Yu-Kun Journal of the Chemical Society, Perkin Transactions 2, Issue 2 https://doi.org/10.1039/p29960000225	journal	January 1996
Photoreduction of double- bridged viologen polymer matrix film. Yang, Yu-Kun; Sun, Xuehui Journal of Photopolymer Science and Technology, Vol. 7, Issue 1 https://doi.org/10.2494/photopolymer.7.193	journal	January 1994

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