Impact of charge switching stimuli on supramolecular perylene monoimide assemblies

Dannenhoffer, Adam; Sai, Hiroaki; Huang, Dongxu; Nagasing, Benjamin; Harutyunyan, Boris; Fairfield, Daniel J.; Aytun, Taner; Chin, Stacey M.; Bedzyk, Michael J.; Olvera de la Cruz, Monica; Stupp, Samuel I.

doi:10.1039/C8SC05595E

Title: Impact of charge switching stimuli on supramolecular perylene monoimide assemblies

Journal Article · Wed Jun 05 00:00:00 EDT 2019 · Chemical Science

DOI:https://doi.org/10.1039/C8SC05595E· OSTI ID:1512525

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^[2]; Huang, Dongxu ^[1];

^[3]; Harutyunyan, Boris ^[4];

^[1]; Aytun, Taner ^[1];

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Department of Materials Science and Engineering, Evanston, USA
Department of Materials Science and Engineering, Evanston, USA, Simpson Querrey Institute, Northwestern University
Department of Chemistry, Northwestern University, Evanston, USA
Department of Physics and Astronomy, Northwestern University, Evanston, USA
Department of Materials Science and Engineering, Evanston, USA, Department of Physics and Astronomy, Northwestern University
Department of Materials Science and Engineering, Evanston, USA, Department of Chemistry, Northwestern University

The development of stimuli-responsive amphiphilic supramolecular nanostructures is an attractive target for systems based on light-absorbing chromophores that can function as photosensitizers in water. We report here on a water soluble supramolecular carboxylated perylene monoimide system in which charge can be switched significantly by a change in pH. This was accomplished by substituting the perylene core with an ionizable hydroxyl group. In acidic environments, crystalline supramolecular nanoribbons with dimensions on the order of 500 × 50 × 2 nm form readily, while in basic solution the additional electrostatic repulsion of the ionized hydroxyl reduces assemblies to very small dimensions on the order of only several nanometers. The HOMO/LUMO levels were also found to be sensitive to pH; in acidic media the HOMO/LUMO levels are –5.65 and –3.70 eV respectively versus vacuum, whereas is in basic conditions they are –4.90 and –3.33 eV, respectively. Utilizing the assemblies as photosensitizers in photocatalytic production of hydrogen with [Mo₃S₁₃]^2– as a catalyst at a pH of 4, H₂ was generated with a turnover number of 125 after 18 hours. Charge switching the assemblies at a pH of 9–10 and using an iron porphyrin catalyst, protons could again be reduced to hydrogen and CO₂ was reduced to CO with a turnover number of 30. The system investigated offers an example of dynamic photosensitizing assemblies that can drive reactions in both acidic and basic media.

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Bio-Inspired Energy Science (CBES)

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

Grant/Contract Number:: DEFG0200ER45810; DESC0001059; FG02-08ER46539; SC0001059; AC02-06CH11357

OSTI ID:: 1512525

Alternate ID(s):: OSTI ID: 1822214; OSTI ID: 1846655

Journal Information:: Chemical Science, Journal Name: Chemical Science Vol. 10 Journal Issue: 22; ISSN 2041-6520

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

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Cited by: 14 works

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References (47)

Synthesis and photophysical properties of new fluorinated benzo[c]xanthene dyes as intracellular pH indicators Liu, Jixiang; Diwu, Zhenjun; Leung, Wai-Yee Bioorganic & Medicinal Chemistry Letters, Vol. 11, Issue 22 https://doi.org/10.1016/S0960-894X(01)00595-9	journal	November 2001
Assembly of Extra-Large Nanosheets by Supramolecular Polymerization of Amphiphilic Pyrene Oligomers in Aqueous Solution Vybornyi, Mykhailo; Rudnev, Alexander; Häner, Robert Chemistry of Materials, Vol. 27, Issue 4 https://doi.org/10.1021/acs.chemmater.5b00047	journal	February 2015
Self-Assembly of a Functional Oligo(Aniline)-Based Amphiphile into Helical Conductive Nanowires Bell, O. Alexander; Wu, Guanglu; Haataja, Johannes S. Journal of the American Chemical Society, Vol. 137, Issue 45 https://doi.org/10.1021/jacs.5b06892	journal	November 2015
3,4:9,10-Perylenebis(dicarboximide) chromophores that function as both electron donors and acceptors Zhao, Yongyu; Wasielewski, Michael R. Tetrahedron Letters, Vol. 40, Issue 39 https://doi.org/10.1016/S0040-4039(99)01468-9	journal	September 1999
Photophysics and Redox Properties of Rylene Imide and Diimide Dyes Alkylated Ortho to the Imide Groups Bullock, Joseph E.; Vagnini, Michael T.; Ramanan, Charusheela The Journal of Physical Chemistry B, Vol. 114, Issue 5 https://doi.org/10.1021/jp908679c	journal	February 2010
Self-Assembled PDINH Supramolecular System for Photocatalysis under Visible Light Liu, Di; Wang, Jun; Bai, Xiaojuan Advanced Materials, Vol. 28, Issue 33 https://doi.org/10.1002/adma.201601168	journal	June 2016
A survey of Hammett substituent constants and resonance and field parameters Hansch, Corwin.; Leo, A.; Taft, R. W. Chemical Reviews, Vol. 91, Issue 2 https://doi.org/10.1021/cr00002a004	journal	March 1991
Self-assembling hydrogel scaffolds for photocatalytic hydrogen production Weingarten, Adam S.; Kazantsev, Roman V.; Palmer, Liam C. Nature Chemistry, Vol. 6, Issue 11 https://doi.org/10.1038/nchem.2075	journal	October 2014
Molecular Control of Internal Crystallization and Photocatalytic Function in Supramolecular Nanostructures Kazantsev, Roman V.; Dannenhoffer, Adam J.; Aytun, Taner Chem, Vol. 4, Issue 7 https://doi.org/10.1016/j.chempr.2018.04.002	journal	July 2018
Visible-Light-Driven Conversion of CO ₂ to CH ₄ with an Organic Sensitizer and an Iron Porphyrin Catalyst Rao, Heng; Lim, Chern-Hooi; Bonin, Julien Journal of the American Chemical Society, Vol. 140, Issue 51 https://doi.org/10.1021/jacs.8b09740	journal	December 2018
Effect of Side-Chain Substituents on Self-Assembly of Perylene Diimide Molecules: Morphology Control Balakrishnan, Kaushik; Datar, Aniket; Naddo, Tammene Journal of the American Chemical Society, Vol. 128, Issue 22 https://doi.org/10.1021/ja061810z	journal	June 2006
Solvent Responsive Micelles Based on Block and Gradient Copoly(2-oxazoline)s Hoogenboom, Richard; Thijs, Hanneke M. L.; Wouters, Daan Macromolecules, Vol. 41, Issue 5 https://doi.org/10.1021/ma702801e	journal	March 2008
Chromophore Dipole Directs Morphology and Photocatalytic Hydrogen Generation Weingarten, Adam S.; Dannenhoffer, Adam J.; Kazantsev, Roman V. Journal of the American Chemical Society, Vol. 140, Issue 15 https://doi.org/10.1021/jacs.7b12641	journal	April 2018
Functional Supramolecular Polymers Aida, T.; Meijer, E. W.; Stupp, S. I. Science, Vol. 335, Issue 6070 https://doi.org/10.1126/science.1205962	journal	February 2012
One-Dimensional Self-Assembly of Planar π-Conjugated Molecules: Adaptable Building Blocks for Organic Nanodevices Zang, Ling; Che, Yanke; Moore, Jeffrey S. Accounts of Chemical Research, Vol. 41, Issue 12 https://doi.org/10.1021/ar800030w	journal	December 2008
Bis( n -octylamino)perylene-3,4:9,10-bis(dicarboximide)s and Their Radical Cations: Synthesis, Electrochemistry, and ENDOR Spectroscopy Ahrens, Michael J.; Tauber, Michael J.; Wasielewski, Michael R. The Journal of Organic Chemistry, Vol. 71, Issue 5 https://doi.org/10.1021/jo052394o	journal	March 2006
One-dimensional self-assembly of a water soluble perylene diimide molecule by pH triggered hydrogelation Datar, Aniket; Balakrishnan, Kaushik; Zang, Ling Chemical Communications, Vol. 49, Issue 61 https://doi.org/10.1039/c3cc43359e	journal	January 2013
Molecular Packing of Amphiphilic Nanosheets Resolved by X-ray Scattering Harutyunyan, Boris; Dannenhoffer, Adam; Kewalramani, Sumit The Journal of Physical Chemistry C, Vol. 121, Issue 2 https://doi.org/10.1021/acs.jpcc.6b11391	journal	January 2017
Solvatochromism and solvent polarity scales Buncel, Erwin; Rajagopal, Srinivasan Accounts of Chemical Research, Vol. 23, Issue 7 https://doi.org/10.1021/ar00175a004	journal	July 1990
Understanding the Mechanism of Gelation and Stimuli-Responsive Nature of a Class of Metallo-Supramolecular Gels Weng, Wengui; Beck, J. Benjamin; Jamieson, Alex M. Journal of the American Chemical Society, Vol. 128, Issue 35 https://doi.org/10.1021/ja063408q	journal	September 2006
Extended-Charge-Transfer Excitons in Crystalline Supramolecular Photocatalytic Scaffolds Hestand, Nicholas J.; Kazantsev, Roman V.; Weingarten, Adam S. Journal of the American Chemical Society, Vol. 138, Issue 36 https://doi.org/10.1021/jacs.6b05673	journal	September 2016
Self-Assembly of Perylene Imide Molecules into 1D Nanostructures: Methods, Morphologies, and Applications Chen, Shuai; Slattum, Paul; Wang, Chuanyi Chemical Reviews, Vol. 115, Issue 21 https://doi.org/10.1021/acs.chemrev.5b00312	journal	October 2015
A new group of fluorescent pH-indicators for an extended pH-range Wolfbeis, Otto S.; Marhold, Harry Fresenius' Zeitschrift für analytische Chemie, Vol. 327, Issue 3-4 https://doi.org/10.1007/BF00491840	journal	January 1987
Bending Nanofibers into Nanospirals: Coordination Chemistry as a Tool for Shaping Hydrophobic Assemblies Kossoy, Elizaveta; Weissman, Haim; Rybtchinski, Boris Chemistry - A European Journal, Vol. 21, Issue 1 https://doi.org/10.1002/chem.201404263	journal	November 2014
pH Responsive micelle self-assembled from a new amphiphilic peptide as anti-tumor drug carrier Liang, Ju; Wu, Wen-Lan; Xu, Xiao-Ding Colloids and Surfaces B: Biointerfaces, Vol. 114 https://doi.org/10.1016/j.colsurfb.2013.10.037	journal	February 2014
Highly Soluble Monoamino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties Chen, Kew-Yu; Chang, Che-Wei International Journal of Molecular Sciences, Vol. 15, Issue 12 https://doi.org/10.3390/ijms151222642	journal	December 2014
Nanobelt Self-Assembly from an Organic n-Type Semiconductor: Propoxyethyl-PTCDI Balakrishnan, Kaushik; Datar, Aniket; Oitker, Randy Journal of the American Chemical Society, Vol. 127, Issue 30 https://doi.org/10.1021/ja052940v	journal	August 2005
Morphology Control of Fluorescent Nanoaggregates by Co-Self-Assembly of Wedge- and Dumbbell-Shaped Amphiphilic Perylene Bisimides Zhang, Xin; Chen, Zhijian; Würthner, Frank Journal of the American Chemical Society, Vol. 129, Issue 16 https://doi.org/10.1021/ja070994u	journal	April 2007
Synthesis, Characterization, Physical Properties, and OLED Application of Single BN-Fused Perylene Diimide Li, Gang; Zhao, Yongbiao; Li, Junbo The Journal of Organic Chemistry, Vol. 80, Issue 1 https://doi.org/10.1021/jo502296z	journal	December 2014
pH and Amphiphilic Structure Direct Supramolecular Behavior in Biofunctional Assemblies Moyer, Tyson J.; Finbloom, Joel A.; Chen, Feng Journal of the American Chemical Society, Vol. 136, Issue 42 https://doi.org/10.1021/ja5042429	journal	October 2014
Supramolecular Packing Controls H ₂ Photocatalysis in Chromophore Amphiphile Hydrogels Weingarten, Adam S.; Kazantsev, Roman V.; Palmer, Liam C. Journal of the American Chemical Society, Vol. 137, Issue 48 https://doi.org/10.1021/jacs.5b10027	journal	November 2015
Photophysics of the Fluorescent pH Indicator BCECF Boens, Noël; Qin, Wenwu; Basarić, Nikola The Journal of Physical Chemistry A, Vol. 110, Issue 30 https://doi.org/10.1021/jp0615712	journal	August 2006
pH responding reversible supramolecular self-assembly of water-soluble amino-imidazole-armed perylene diimide dye for biological applications Zhang, Wei; Gan, Shi-Yu; Li, Feng-Hua RSC Advances, Vol. 5, Issue 3 https://doi.org/10.1039/C4RA11124A	journal	January 2015
Crystal-Phase Transitions and Photocatalysis in Supramolecular Scaffolds Kazantsev, Roman V.; Dannenhoffer, Adam J.; Weingarten, Adam S. Journal of the American Chemical Society, Vol. 139, Issue 17 https://doi.org/10.1021/jacs.6b13156	journal	April 2017
Rational Design of Multiple-Stimulus-Responsive Materials via Supramolecular Self-Assembly Gong, Yanjun; Jiao, Tiliu; Hu, Qiongzheng The Journal of Physical Chemistry C, Vol. 119, Issue 28 https://doi.org/10.1021/acs.jpcc.5b03220	journal	June 2015
pH dependent photocatalytic hydrogen evolution by self-assembled perylene bisimides Nolan, Michael C.; Walsh, James J.; Mears, Laura L. E. Journal of Materials Chemistry A, Vol. 5, Issue 16 https://doi.org/10.1039/C7TA01845B	journal	January 2017
Perylene-3,4,9,10-tetracarboxylic Acid Diimides: Synthesis, Physical Properties, and Use in Organic Electronics Huang, Chun; Barlow, Stephen; Marder, Seth R. The Journal of Organic Chemistry, Vol. 76, Issue 8 https://doi.org/10.1021/jo2001963	journal	April 2011
¹⁹ F Magnetic Resonance Imaging Signals from Peptide Amphiphile Nanostructures Are Strongly Affected by Their Shape Preslar, Adam T.; Tantakitti, Faifan; Park, Kitae ACS Nano, Vol. 10, Issue 8 https://doi.org/10.1021/acsnano.6b00267	journal	July 2016
Di(alkoxy)- and Di(alkylthio)-Substituted Perylene-3,4;9,10-tetracarboxy Diimides with Tunable Electrochemical and Photophysical Properties Zhao, Chuntao; Zhang, Yuexing; Li, Renjie The Journal of Organic Chemistry, Vol. 72, Issue 7 https://doi.org/10.1021/jo062150j	journal	March 2007
Dynamic Materials through Metal-Directed and Solvent-Driven Self-Assembly of Cavitands Pirondini, Laura; Stendardo, Anna G.; Geremia, Silvano Angewandte Chemie International Edition, Vol. 42, Issue 12 https://doi.org/10.1002/anie.200390355	journal	March 2003
A Columnar Liquid-Crystal Phase Formed by Hydrogen-Bonded Perylene Bisimide J-Aggregates Herbst, Stefanie; Soberats, Bartolome; Leowanawat, Pawaret Angewandte Chemie International Edition, Vol. 56, Issue 8 https://doi.org/10.1002/anie.201612047	journal	January 2017
Photophysical and Electrochemical Properties of 1,7-Diaryl-Substituted Perylene Diimides Chao, Chun-Chieh; Leung, Man-kit; Su, Yuhlong Oliver The Journal of Organic Chemistry, Vol. 70, Issue 11 https://doi.org/10.1021/jo050001f	journal	May 2005
Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials Würthner, Frank; Saha-Möller, Chantu R.; Fimmel, Benjamin Chemical Reviews, Vol. 116, Issue 3 https://doi.org/10.1021/acs.chemrev.5b00188	journal	August 2015
Self-Assembly of Light-Harvesting Crystalline Nanosheets in Aqueous Media Shahar, Chen; Baram, Jonathan; Tidhar, Yaron ACS Nano, Vol. 7, Issue 4 https://doi.org/10.1021/nn400484y	journal	April 2013
Thermally Responsive Pulsating Nanotubules Zhang, W.; Aida, T. Science, Vol. 337, Issue 6101 https://doi.org/10.1126/science.1228178	journal	September 2012
Cyanated Perylene-3,4-dicarboximides and Perylene-3,4:9,10-bis(dicarboximide): Facile Chromophoric Oxidants for Organic Photonics and Electronics Ahrens, Michael J.; Fuller, Michael J.; Wasielewski, Michael R. Chemistry of Materials, Vol. 15, Issue 14 https://doi.org/10.1021/cm034140u	journal	July 2003
Solvatochromism of dyes. Part I. Solvatochromism of merocyanines. Derivatives of the 7H-indolo [1,2-a] quinolinium system. A new model of solvatochromism Soroka, Jacek A.; Soroka, Krystyna B. Journal of Physical Organic Chemistry, Vol. 4, Issue 10 https://doi.org/10.1002/poc.610041003	journal	October 1991

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Title: Impact of charge switching stimuli on supramolecular perylene monoimide assemblies

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