skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

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

Abstract

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

Authors:
ORCiD logo [1]; ORCiD logo [2];  [1]; ORCiD logo [3];  [4]; ORCiD logo [1];  [1]; ORCiD logo [3]; ORCiD logo [5]; ORCiD logo [6]; ORCiD logo [6]
  1. Department of Materials Science and Engineering, Evanston, USA
  2. Department of Materials Science and Engineering, Evanston, USA, Simpson Querrey Institute, Northwestern University
  3. Department of Chemistry, Northwestern University, Evanston, USA
  4. Department of Physics and Astronomy, Northwestern University, Evanston, USA
  5. Department of Materials Science and Engineering, Evanston, USA, Department of Physics and Astronomy, Northwestern University
  6. Department of Materials Science and Engineering, Evanston, USA, Department of Chemistry, Northwestern University
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1512525
Grant/Contract Number:  
DEFG0200ER45810; DESC0001059; FG02-08ER46539
Resource Type:
Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Name: Chemical Science Journal Volume: 10 Journal Issue: 22; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

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, and Stupp, Samuel I. Impact of charge switching stimuli on supramolecular perylene monoimide assemblies. United Kingdom: N. p., 2019. Web. doi:10.1039/C8SC05595E.
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. Impact of charge switching stimuli on supramolecular perylene monoimide assemblies. United Kingdom. doi:10.1039/C8SC05595E.
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, and Stupp, Samuel I. Wed . "Impact of charge switching stimuli on supramolecular perylene monoimide assemblies". United Kingdom. doi:10.1039/C8SC05595E.
@article{osti_1512525,
title = {Impact of charge switching stimuli on supramolecular perylene monoimide assemblies},
author = {Dannenhoffer, Adam and Sai, Hiroaki and Huang, Dongxu and Nagasing, Benjamin and Harutyunyan, Boris and Fairfield, Daniel J. and Aytun, Taner and Chin, Stacey M. and Bedzyk, Michael J. and Olvera de la Cruz, Monica and Stupp, Samuel I.},
abstractNote = {A switchable perylene monoimide which undergoes reversible morphological and electronic changes controlled by the ionization state of the phenolic oxygen.},
doi = {10.1039/C8SC05595E},
journal = {Chemical Science},
number = 22,
volume = 10,
place = {United Kingdom},
year = {2019},
month = {6}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1039/C8SC05595E

Save / Share:

Works referenced in this record:

Synthesis and photophysical properties of new fluorinated benzo[c]xanthene dyes as intracellular pH indicators
journal, November 2001


Assembly of Extra-Large Nanosheets by Supramolecular Polymerization of Amphiphilic Pyrene Oligomers in Aqueous Solution
journal, February 2015


Self-Assembly of a Functional Oligo(Aniline)-Based Amphiphile into Helical Conductive Nanowires
journal, November 2015

  • Bell, O. Alexander; Wu, Guanglu; Haataja, Johannes S.
  • Journal of the American Chemical Society, Vol. 137, Issue 45
  • DOI: 10.1021/jacs.5b06892

3,4:9,10-Perylenebis(dicarboximide) chromophores that function as both electron donors and acceptors
journal, September 1999


Photophysics and Redox Properties of Rylene Imide and Diimide Dyes Alkylated Ortho to the Imide Groups
journal, February 2010

  • Bullock, Joseph E.; Vagnini, Michael T.; Ramanan, Charusheela
  • The Journal of Physical Chemistry B, Vol. 114, Issue 5
  • DOI: 10.1021/jp908679c

Self-Assembled PDINH Supramolecular System for Photocatalysis under Visible Light
journal, June 2016


A survey of Hammett substituent constants and resonance and field parameters
journal, March 1991

  • Hansch, Corwin.; Leo, A.; Taft, R. W.
  • Chemical Reviews, Vol. 91, Issue 2
  • DOI: 10.1021/cr00002a004

Self-assembling hydrogel scaffolds for photocatalytic hydrogen production
journal, October 2014

  • Weingarten, Adam S.; Kazantsev, Roman V.; Palmer, Liam C.
  • Nature Chemistry, Vol. 6, Issue 11
  • DOI: 10.1038/nchem.2075

Molecular Control of Internal Crystallization and Photocatalytic Function in Supramolecular Nanostructures
journal, July 2018


Visible-Light-Driven Conversion of CO 2 to CH 4 with an Organic Sensitizer and an Iron Porphyrin Catalyst
journal, December 2018

  • Rao, Heng; Lim, Chern-Hooi; Bonin, Julien
  • Journal of the American Chemical Society, Vol. 140, Issue 51
  • DOI: 10.1021/jacs.8b09740

Effect of Side-Chain Substituents on Self-Assembly of Perylene Diimide Molecules:  Morphology Control
journal, June 2006

  • Balakrishnan, Kaushik; Datar, Aniket; Naddo, Tammene
  • Journal of the American Chemical Society, Vol. 128, Issue 22
  • DOI: 10.1021/ja061810z

Solvent Responsive Micelles Based on Block and Gradient Copoly(2-oxazoline)s
journal, March 2008

  • Hoogenboom, Richard; Thijs, Hanneke M. L.; Wouters, Daan
  • Macromolecules, Vol. 41, Issue 5
  • DOI: 10.1021/ma702801e

Chromophore Dipole Directs Morphology and Photocatalytic Hydrogen Generation
journal, April 2018

  • Weingarten, Adam S.; Dannenhoffer, Adam J.; Kazantsev, Roman V.
  • Journal of the American Chemical Society, Vol. 140, Issue 15
  • DOI: 10.1021/jacs.7b12641

Functional Supramolecular Polymers
journal, February 2012


One-Dimensional Self-Assembly of Planar π-Conjugated Molecules: Adaptable Building Blocks for Organic Nanodevices
journal, December 2008

  • Zang, Ling; Che, Yanke; Moore, Jeffrey S.
  • Accounts of Chemical Research, Vol. 41, Issue 12
  • DOI: 10.1021/ar800030w

Bis( n -octylamino)perylene-3,4:9,10-bis(dicarboximide)s and Their Radical Cations:  Synthesis, Electrochemistry, and ENDOR Spectroscopy
journal, March 2006

  • Ahrens, Michael J.; Tauber, Michael J.; Wasielewski, Michael R.
  • The Journal of Organic Chemistry, Vol. 71, Issue 5
  • DOI: 10.1021/jo052394o

One-dimensional self-assembly of a water soluble perylene diimide molecule by pH triggered hydrogelation
journal, January 2013

  • Datar, Aniket; Balakrishnan, Kaushik; Zang, Ling
  • Chemical Communications, Vol. 49, Issue 61
  • DOI: 10.1039/c3cc43359e

Molecular Packing of Amphiphilic Nanosheets Resolved by X-ray Scattering
journal, January 2017

  • Harutyunyan, Boris; Dannenhoffer, Adam; Kewalramani, Sumit
  • The Journal of Physical Chemistry C, Vol. 121, Issue 2
  • DOI: 10.1021/acs.jpcc.6b11391

Solvatochromism and solvent polarity scales
journal, July 1990

  • Buncel, Erwin; Rajagopal, Srinivasan
  • Accounts of Chemical Research, Vol. 23, Issue 7
  • DOI: 10.1021/ar00175a004

Understanding the Mechanism of Gelation and Stimuli-Responsive Nature of a Class of Metallo-Supramolecular Gels
journal, September 2006

  • Weng, Wengui; Beck, J. Benjamin; Jamieson, Alex M.
  • Journal of the American Chemical Society, Vol. 128, Issue 35
  • DOI: 10.1021/ja063408q

Extended-Charge-Transfer Excitons in Crystalline Supramolecular Photocatalytic Scaffolds
journal, September 2016

  • Hestand, Nicholas J.; Kazantsev, Roman V.; Weingarten, Adam S.
  • Journal of the American Chemical Society, Vol. 138, Issue 36
  • DOI: 10.1021/jacs.6b05673

Self-Assembly of Perylene Imide Molecules into 1D Nanostructures: Methods, Morphologies, and Applications
journal, October 2015


A new group of fluorescent pH-indicators for an extended pH-range
journal, January 1987

  • Wolfbeis, Otto S.; Marhold, Harry
  • Fresenius' Zeitschrift für analytische Chemie, Vol. 327, Issue 3-4
  • DOI: 10.1007/BF00491840

Bending Nanofibers into Nanospirals: Coordination Chemistry as a Tool for Shaping Hydrophobic Assemblies
journal, November 2014

  • Kossoy, Elizaveta; Weissman, Haim; Rybtchinski, Boris
  • Chemistry - A European Journal, Vol. 21, Issue 1
  • DOI: 10.1002/chem.201404263

pH Responsive micelle self-assembled from a new amphiphilic peptide as anti-tumor drug carrier
journal, February 2014


Highly Soluble Monoamino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis, Optical and Electrochemical Properties
journal, December 2014

  • Chen, Kew-Yu; Chang, Che-Wei
  • International Journal of Molecular Sciences, Vol. 15, Issue 12
  • DOI: 10.3390/ijms151222642

Nanobelt Self-Assembly from an Organic n-Type Semiconductor:  Propoxyethyl-PTCDI
journal, August 2005

  • Balakrishnan, Kaushik; Datar, Aniket; Oitker, Randy
  • Journal of the American Chemical Society, Vol. 127, Issue 30
  • DOI: 10.1021/ja052940v

Morphology Control of Fluorescent Nanoaggregates by Co-Self-Assembly of Wedge- and Dumbbell-Shaped Amphiphilic Perylene Bisimides
journal, April 2007

  • Zhang, Xin; Chen, Zhijian; Würthner, Frank
  • Journal of the American Chemical Society, Vol. 129, Issue 16
  • DOI: 10.1021/ja070994u

Synthesis, Characterization, Physical Properties, and OLED Application of Single BN-Fused Perylene Diimide
journal, December 2014

  • Li, Gang; Zhao, Yongbiao; Li, Junbo
  • The Journal of Organic Chemistry, Vol. 80, Issue 1
  • DOI: 10.1021/jo502296z

pH and Amphiphilic Structure Direct Supramolecular Behavior in Biofunctional Assemblies
journal, October 2014

  • Moyer, Tyson J.; Finbloom, Joel A.; Chen, Feng
  • Journal of the American Chemical Society, Vol. 136, Issue 42
  • DOI: 10.1021/ja5042429

Supramolecular Packing Controls H 2 Photocatalysis in Chromophore Amphiphile Hydrogels
journal, November 2015

  • Weingarten, Adam S.; Kazantsev, Roman V.; Palmer, Liam C.
  • Journal of the American Chemical Society, Vol. 137, Issue 48
  • DOI: 10.1021/jacs.5b10027

Photophysics of the Fluorescent pH Indicator BCECF
journal, August 2006

  • Boens, Noël; Qin, Wenwu; Basarić, Nikola
  • The Journal of Physical Chemistry A, Vol. 110, Issue 30
  • DOI: 10.1021/jp0615712

Crystal-Phase Transitions and Photocatalysis in Supramolecular Scaffolds
journal, April 2017

  • Kazantsev, Roman V.; Dannenhoffer, Adam J.; Weingarten, Adam S.
  • Journal of the American Chemical Society, Vol. 139, Issue 17
  • DOI: 10.1021/jacs.6b13156

Rational Design of Multiple-Stimulus-Responsive Materials via Supramolecular Self-Assembly
journal, June 2015

  • Gong, Yanjun; Jiao, Tiliu; Hu, Qiongzheng
  • The Journal of Physical Chemistry C, Vol. 119, Issue 28
  • DOI: 10.1021/acs.jpcc.5b03220

pH dependent photocatalytic hydrogen evolution by self-assembled perylene bisimides
journal, January 2017

  • Nolan, Michael C.; Walsh, James J.; Mears, Laura L. E.
  • Journal of Materials Chemistry A, Vol. 5, Issue 16
  • DOI: 10.1039/C7TA01845B

Perylene-3,4,9,10-tetracarboxylic Acid Diimides: Synthesis, Physical Properties, and Use in Organic Electronics
journal, April 2011

  • Huang, Chun; Barlow, Stephen; Marder, Seth R.
  • The Journal of Organic Chemistry, Vol. 76, Issue 8
  • DOI: 10.1021/jo2001963

19 F Magnetic Resonance Imaging Signals from Peptide Amphiphile Nanostructures Are Strongly Affected by Their Shape
journal, July 2016


Di(alkoxy)- and Di(alkylthio)-Substituted Perylene-3,4;9,10-tetracarboxy Diimides with Tunable Electrochemical and Photophysical Properties
journal, March 2007

  • Zhao, Chuntao; Zhang, Yuexing; Li, Renjie
  • The Journal of Organic Chemistry, Vol. 72, Issue 7
  • DOI: 10.1021/jo062150j

Dynamic Materials through Metal-Directed and Solvent-Driven Self-Assembly of Cavitands
journal, March 2003

  • Pirondini, Laura; Stendardo, Anna G.; Geremia, Silvano
  • Angewandte Chemie International Edition, Vol. 42, Issue 12
  • DOI: 10.1002/anie.200390355

A Columnar Liquid-Crystal Phase Formed by Hydrogen-Bonded Perylene Bisimide J-Aggregates
journal, January 2017

  • Herbst, Stefanie; Soberats, Bartolome; Leowanawat, Pawaret
  • Angewandte Chemie International Edition, Vol. 56, Issue 8
  • DOI: 10.1002/anie.201612047

Photophysical and Electrochemical Properties of 1,7-Diaryl-Substituted Perylene Diimides
journal, May 2005

  • Chao, Chun-Chieh; Leung, Man-kit; Su, Yuhlong Oliver
  • The Journal of Organic Chemistry, Vol. 70, Issue 11
  • DOI: 10.1021/jo050001f

Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials
journal, August 2015


Self-Assembly of Light-Harvesting Crystalline Nanosheets in Aqueous Media
journal, April 2013

  • Shahar, Chen; Baram, Jonathan; Tidhar, Yaron
  • ACS Nano, Vol. 7, Issue 4
  • DOI: 10.1021/nn400484y

Thermally Responsive Pulsating Nanotubules
journal, September 2012


Cyanated Perylene-3,4-dicarboximides and Perylene-3,4:9,10-bis(dicarboximide):  Facile Chromophoric Oxidants for Organic Photonics and Electronics
journal, July 2003

  • Ahrens, Michael J.; Fuller, Michael J.; Wasielewski, Michael R.
  • Chemistry of Materials, Vol. 15, Issue 14
  • DOI: 10.1021/cm034140u

Solvatochromism of dyes. Part I. Solvatochromism of merocyanines. Derivatives of the 7H-indolo [1,2-a] quinolinium system. A new model of solvatochromism
journal, October 1991

  • Soroka, Jacek A.; Soroka, Krystyna B.
  • Journal of Physical Organic Chemistry, Vol. 4, Issue 10
  • DOI: 10.1002/poc.610041003