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 · 05 June 2019 · Chemical Science

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

^[1];

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

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

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

^[3];

^[5];

^[6];

^[6]

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

A switchable perylene monoimide which undergoes reversible morphological and electronic changes controlled by the ionization state of the phenolic oxygen.

View Journal Article

Cite

Export

Save

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

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

Grant/Contract Number:: AC02-06CH11357; FG02-00ER45810; FG02-08ER46539; SC0001059

OSTI ID:: 1512525

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

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

Country of Publication:: United Kingdom

Language:: English

References (48)

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
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
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
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
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
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
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
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
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
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
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 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures Würthner, Frank Chem. Commun., Issue 14 https://doi.org/10.1039/B401630K	journal	January 2004
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
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
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
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
Thermally Responsive Pulsating Nanotubules Zhang, W.; Aida, T. Science, Vol. 337, Issue 6101 https://doi.org/10.1126/science.1228178	journal	September 2012
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

Similar Records

Impact of charge switching stimuli on supramolecular perylene monoimide assemblies

Journal Article · 2019 · Chem. Sci. · OSTI ID:1531004

Dannenhoffer, Adam; Sai, Hiroaki; Huang, Dongxu; +7 more

Long-lived triplet excited state in a platinum(ii) perylene monoimide complex

Journal Article · 2018 · Dalton Transactions · OSTI ID:1633630

Yarnell, James E.; Chakraborty, Arnab; Myahkostupov, Mykhaylo; +2 more

pH- and temperature-responsive supramolecular assemblies with highly adjustable viscoelasticity: a multi-stimuli binary system

Journal Article · 2023 · Soft Matter · OSTI ID:2418204

Lin, Yu-Ting; Liu, Shuhao; Bhat, Bhargavi; +5 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
99 GENERAL AND MISCELLANEOUS

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

Citation Formats

References (48)

Similar Records

Related Subjects