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

Title: Supramolecular polymerization provides non-equilibrium product distributions of imine-linked macrocycles

Abstract

Supramolecular polymerization of imine-linked macrocycles has been coupled to dynamic imine bond exchange within a series of macrocycles and oligomers.

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]
  1. Department of Chemistry, Northwestern University, Evanston, 60208 USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1592183
Grant/Contract Number:  
DGE-1324585
Resource Type:
Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Name: Chemical Science; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Strauss, Michael J., Evans, Austin M., Castano, Ioannina, Li, Rebecca L., and Dichtel, William R. Supramolecular polymerization provides non-equilibrium product distributions of imine-linked macrocycles. United Kingdom: N. p., 2020. Web. doi:10.1039/C9SC05422G.
Strauss, Michael J., Evans, Austin M., Castano, Ioannina, Li, Rebecca L., & Dichtel, William R. Supramolecular polymerization provides non-equilibrium product distributions of imine-linked macrocycles. United Kingdom. doi:10.1039/C9SC05422G.
Strauss, Michael J., Evans, Austin M., Castano, Ioannina, Li, Rebecca L., and Dichtel, William R. Wed . "Supramolecular polymerization provides non-equilibrium product distributions of imine-linked macrocycles". United Kingdom. doi:10.1039/C9SC05422G.
@article{osti_1592183,
title = {Supramolecular polymerization provides non-equilibrium product distributions of imine-linked macrocycles},
author = {Strauss, Michael J. and Evans, Austin M. and Castano, Ioannina and Li, Rebecca L. and Dichtel, William R.},
abstractNote = {Supramolecular polymerization of imine-linked macrocycles has been coupled to dynamic imine bond exchange within a series of macrocycles and oligomers.},
doi = {10.1039/C9SC05422G},
journal = {Chemical Science},
number = ,
volume = ,
place = {United Kingdom},
year = {2020},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1039/C9SC05422G

Save / Share:

Works referenced in this record:

Supramolecular Block Copolymers under Thermodynamic Control
journal, May 2018

  • Adelizzi, Beatrice; Aloi, Antonio; Markvoort, Albert J.
  • Journal of the American Chemical Society, Vol. 140, Issue 23
  • DOI: 10.1021/jacs.8b02706

Mechanism of Self-Assembly Process and Seeded Supramolecular Polymerization of Perylene Bisimide Organogelator
journal, February 2015

  • Ogi, Soichiro; Stepanenko, Vladimir; Sugiyasu, Kazunori
  • Journal of the American Chemical Society, Vol. 137, Issue 9
  • DOI: 10.1021/ja511952c

Kinetic Analysis as a Tool to Distinguish Pathway Complexity in Molecular Assembly: An Unexpected Outcome of Structures in Competition
journal, September 2015

  • van der Zwaag, Daan; Pieters, Pascal A.; Korevaar, Peter A.
  • Journal of the American Chemical Society, Vol. 137, Issue 39
  • DOI: 10.1021/jacs.5b08138

Anion induced supramolecular polymerization: a novel approach for the ultrasensitive detection and separation of F −
journal, January 2019

  • Lin, Qi; Gong, Guan-Fei; Fan, Yan-Qing
  • Chemical Communications, Vol. 55, Issue 22
  • DOI: 10.1039/C8CC09876J

Non-Centrosymmetric Cylindrical Micelles by Unidirectional Growth
journal, August 2012


Dynamic Combinatorial Evolution within Self-Replicating Supramolecular Assemblies
journal, January 2009

  • Nguyen, Rémi; Allouche, Lionel; Buhler, Eric
  • Angewandte Chemie International Edition, Vol. 48, Issue 6
  • DOI: 10.1002/anie.200804602

Protonic and Temperature Modulation of Constituent Expression by Component Selection in a Dynamic Combinatorial Library of Imines
journal, February 2006

  • Giuseppone, Nicolas; Lehn, Jean-Marie
  • Chemistry - A European Journal, Vol. 12, Issue 6
  • DOI: 10.1002/chem.200501038

A rational strategy for the realization of chain-growth supramolecular polymerization
journal, February 2015


Equilibration of Imine-Linked Polymers to Hexagonal Macrocycles Driven by Self-Assembly
journal, February 2018

  • Chavez, Anton D.; Evans, Austin M.; Flanders, Nathan C.
  • Chemistry - A European Journal, Vol. 24, Issue 16
  • DOI: 10.1002/chem.201800459

Kinetic control in the temperature-dependent sequential growth of surface-confined supramolecular copolymers
journal, January 2017

  • Engel, Sabrina; Spitzer, Daniel; Rodrigues, Leona Lucas
  • Faraday Discussions, Vol. 204
  • DOI: 10.1039/C7FD00100B

Functional Supramolecular Polymers
journal, February 2012


Multidimensional hierarchical self-assembly of amphiphilic cylindrical block comicelles
journal, March 2015


Supramolecular Linear Heterojunction Composed of Graphite-Like Semiconducting Nanotubular Segments
journal, October 2011


Highly Ordered n / p -Co-assembled Materials with Remarkable Charge Mobilities
journal, January 2015

  • López-Andarias, Javier; Rodriguez, María José; Atienza, Carmen
  • Journal of the American Chemical Society, Vol. 137, Issue 2
  • DOI: 10.1021/ja510946c

High aspect ratio nanotubes assembled from macrocyclic iminium salts
journal, August 2018

  • Sun, Chao; Shen, Meng; Chavez, Anton D.
  • Proceedings of the National Academy of Sciences, Vol. 115, Issue 36
  • DOI: 10.1073/pnas.1809383115

Living supramolecular polymerization
journal, July 2015


Molecular Basis for Water-Promoted Supramolecular Chirality Inversion in Helical Rosette Nanotubes
journal, May 2007

  • Johnson, Ross S.; Yamazaki, Takeshi; Kovalenko, Andriy
  • Journal of the American Chemical Society, Vol. 129, Issue 17
  • DOI: 10.1021/ja0706192

Cooperative Self-Assembly of Pyridine-2,6-Diimine-Linked Macrocycles into Mechanically Robust Nanotubes
journal, September 2019

  • Strauss, Michael J.; Asheghali, Darya; Evans, Austin M.
  • Angewandte Chemie International Edition, Vol. 58, Issue 41
  • DOI: 10.1002/anie.201907668

Solvent Clathrate Driven Dynamic Stereomutation of a Supramolecular Polymer with Molecular Pockets
journal, September 2017

  • Kulkarni, Chidambar; Korevaar, Peter A.; Bejagam, Karteek K.
  • Journal of the American Chemical Society, Vol. 139, Issue 39
  • DOI: 10.1021/jacs.7b07639

Pathway Complexity in π-Conjugated Materials
journal, September 2013

  • Korevaar, Peter A.; de Greef, Tom F. A.; Meijer, E. W.
  • Chemistry of Materials, Vol. 26, Issue 1
  • DOI: 10.1021/cm4021172

Enzyme-assisted self-assembly under thermodynamic control
journal, December 2008

  • Williams, Richard J.; Smith, Andrew M.; Collins, Richard
  • Nature Nanotechnology, Vol. 4, Issue 1
  • DOI: 10.1038/nnano.2008.378

Kinetic and Thermodynamic Selectivity in Subcomponent Substitution
journal, April 2007

  • Schultz, David; Nitschke, Jonathan R.
  • Chemistry - A European Journal, Vol. 13, Issue 13
  • DOI: 10.1002/chem.200601693

Structure-stability correlations for imine formation in aqueous solution
journal, October 2005

  • Godoy-Alcántar, C.; Yatsimirsky, Anatoly K.; Lehn, J. -M.
  • Journal of Physical Organic Chemistry, Vol. 18, Issue 10
  • DOI: 10.1002/poc.941

Mechanosensitive Self-Replication Driven by Self-Organization
journal, March 2010


Controlling and imaging biomimetic self-assembly
journal, November 2015

  • Aliprandi, Alessandro; Mauro, Matteo; De Cola, Luisa
  • Nature Chemistry, Vol. 8, Issue 1
  • DOI: 10.1038/nchem.2383

Supramolecular block copolymers by kinetically controlled co-self-assembly of planar and core-twisted perylene bisimides
journal, May 2015

  • Görl, Daniel; Zhang, Xin; Stepanenko, Vladimir
  • Nature Communications, Vol. 6, Issue 1
  • DOI: 10.1038/ncomms8009

“Soldier–Sergeant–Soldier” triblock copolymers: revealing the folded structure of single-chain polymeric nanoparticles
journal, January 2014

  • Hosono, Nobuhiko; Palmans, Anja R. A.; Meijer, E. W.
  • Chem. Commun., Vol. 50, Issue 59
  • DOI: 10.1039/C4CC02789B

Kinetic Selectivity and Thermodynamic Features of Competitive Imine Formation in Dynamic Covalent Chemistry
journal, July 2017

  • Kulchat, Sirinan; Chaur, Manuel N.; Lehn, Jean-Marie
  • Chemistry - A European Journal, Vol. 23, Issue 46
  • DOI: 10.1002/chem.201702088

Insight into the Mechanisms of Cooperative Self-Assembly:  The “Sergeants-and-Soldiers” Principle of Chiral and Achiral C 3 -Symmetrical Discotic Triamides
journal, January 2008

  • Smulders, Maarten M. J.; Schenning, Albertus P. H. J.; Meijer, E. W.
  • Journal of the American Chemical Society, Vol. 130, Issue 2
  • DOI: 10.1021/ja075987k

Chiral Memory via Chiral Amplification and Selective Depolymerization of Porphyrin Aggregates
journal, December 2010

  • Helmich, Floris; Lee, Cameron C.; Schenning, Albertus P. H. J.
  • Journal of the American Chemical Society, Vol. 132, Issue 47
  • DOI: 10.1021/ja1077602

Multicomponent Supramolecular Polymers as a Modular Platform for Intracellular Delivery
journal, January 2016


Amplification of Chirality:  The “Sergeants and Soldiers” Principle Applied to Dynamic Hydrogen-Bonded Assemblies
journal, October 2001

  • Prins, Leonard J.; Timmerman, Peter; Reinhoudt, David N.
  • Journal of the American Chemical Society, Vol. 123, Issue 42
  • DOI: 10.1021/ja010610e

Living supramolecular polymerization realized through a biomimetic approach
journal, February 2014

  • Ogi, Soichiro; Sugiyasu, Kazunori; Manna, Swarup
  • Nature Chemistry, Vol. 6, Issue 3
  • DOI: 10.1038/nchem.1849

Supramolecular helical nanofibers formed by an achiral monopyrrolotetrathiafulvalene derivative: water-triggered gelation and chiral evolution
journal, January 2017

  • Liu, Yucun; Jia, Yu; Zhu, Enwei
  • New Journal of Chemistry, Vol. 41, Issue 19
  • DOI: 10.1039/C7NJ02215H

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


Thermally bisignate supramolecular polymerization
journal, June 2017

  • Venkata Rao, Kotagiri; Miyajima, Daigo; Nihonyanagi, Atsuko
  • Nature Chemistry, Vol. 9, Issue 11
  • DOI: 10.1038/nchem.2812