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

Title: Equilibration of Imine-Linked Polymers to Hexagonal Macrocycles Driven by Self-Assembly

Authors:
 [1];  [2];  [2]; ORCiD logo [1]; ORCiD logo [2];  [3]; ORCiD logo [2]
  1. Department of Chemistry, Northwestern University, Evanston Illinois 60208 USA, Department of Chemistry and Chemical Biology, Cornell University, Ithaca New York 14853 USA
  2. Department of Chemistry, Northwestern University, Evanston Illinois 60208 USA
  3. Department of Chemistry, Northwestern University, Evanston Illinois 60208 USA, Chemical Sciences and Engineering Division, Argonne National Laboratory, Argonne Illinois 60439 USA
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1422635
Grant/Contract Number:  
AC02-06CH11357
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Chemistry - A European Journal
Additional Journal Information:
Journal Name: Chemistry - A European Journal Journal Volume: 24 Journal Issue: 16; Journal ID: ISSN 0947-6539
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Chavez, Anton D., Evans, Austin M., Flanders, Nathan C., Bisbey, Ryan P., Vitaku, Edon, Chen, Lin X., and Dichtel, William R. Equilibration of Imine-Linked Polymers to Hexagonal Macrocycles Driven by Self-Assembly. Germany: N. p., 2018. Web. doi:10.1002/chem.201800459.
Chavez, Anton D., Evans, Austin M., Flanders, Nathan C., Bisbey, Ryan P., Vitaku, Edon, Chen, Lin X., & Dichtel, William R. Equilibration of Imine-Linked Polymers to Hexagonal Macrocycles Driven by Self-Assembly. Germany. doi:10.1002/chem.201800459.
Chavez, Anton D., Evans, Austin M., Flanders, Nathan C., Bisbey, Ryan P., Vitaku, Edon, Chen, Lin X., and Dichtel, William R. Mon . "Equilibration of Imine-Linked Polymers to Hexagonal Macrocycles Driven by Self-Assembly". Germany. doi:10.1002/chem.201800459.
@article{osti_1422635,
title = {Equilibration of Imine-Linked Polymers to Hexagonal Macrocycles Driven by Self-Assembly},
author = {Chavez, Anton D. and Evans, Austin M. and Flanders, Nathan C. and Bisbey, Ryan P. and Vitaku, Edon and Chen, Lin X. and Dichtel, William R.},
abstractNote = {},
doi = {10.1002/chem.201800459},
journal = {Chemistry - A European Journal},
number = 16,
volume = 24,
place = {Germany},
year = {2018},
month = {2}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1002/chem.201800459

Citation Metrics:
Cited by: 3 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Template Synthesis of Gold Nanoparticles with an Organic Molecular Cage
journal, January 2014

  • McCaffrey, Ryan; Long, Hai; Jin, Yinghua
  • Journal of the American Chemical Society, Vol. 136, Issue 5
  • DOI: 10.1021/ja412606t

Moving Beyond Boron: The Emergence of New Linkage Chemistries in Covalent Organic Frameworks
journal, June 2016


Konjugierte Makrocyclen: Konzepte und Anwendungen
journal, September 2011

  • Iyoda, Masahiko; Yamakawa, Jun; Rahman, M. Jalilur
  • Angewandte Chemie, Vol. 123, Issue 45
  • DOI: 10.1002/ange.201006198

Arylene–ethynylene macrocycles: Privileged shape-persistent building blocks for organic materials
journal, March 2012

  • Gross, Dustin E.; Zang, Ling; Moore, Jeffrey S.
  • Pure and Applied Chemistry, Vol. 84, Issue 4
  • DOI: 10.1351/PAC-CON-11-09-15

Reaction Pathways Leading to Arylene Ethynylene Macrocycles via Alkyne Metathesis
journal, August 2005

  • Zhang, Wei; Moore, Jeffrey S.
  • Journal of the American Chemical Society, Vol. 127, Issue 33
  • DOI: 10.1021/ja053466w

The atom, the molecule, and the covalent organic framework
journal, March 2017


Covalent Organic Frameworks as a Platform for Multidimensional Polymerization
journal, May 2017


Decoding the Morphological Diversity in Two Dimensional Crystalline Porous Polymers by Core Planarity Modulation
journal, March 2016

  • Halder, Arjun; Kandambeth, Sharath; Biswal, Bishnu P.
  • Angewandte Chemie International Edition, Vol. 55, Issue 27
  • DOI: 10.1002/anie.201600087

Insight into the crystallization of amorphous imine-linked polymer networks to 2D covalent organic frameworks
journal, January 2016

  • Smith, Brian J.; Overholts, Anna C.; Hwang, Nicky
  • Chemical Communications, Vol. 52, Issue 18
  • DOI: 10.1039/C5CC10221A

Self-Assembling Organic Nanotubes with Precisely Defined, Sub-nanometer Pores: Formation and Mass Transport Characteristics
journal, January 2013

  • Gong, Bing; Shao, Zhifeng
  • Accounts of Chemical Research, Vol. 46, Issue 12
  • DOI: 10.1021/ar400030e

Gram-scale synthesis of two-dimensional polymer crystals and their structure analysis by X-ray diffraction
journal, July 2014

  • Kory, Max J.; Wörle, Michael; Weber, Thomas
  • Nature Chemistry, Vol. 6, Issue 9
  • DOI: 10.1038/nchem.2007

Macrocyclization under thermodynamic control. A theoretical study and its application to the equilibrium cyclooligomerization of .beta.-propiolactone
journal, May 1993

  • Ercolani, Gianfranco; Mandolini, Luigi; Mencarelli, Paolo
  • Journal of the American Chemical Society, Vol. 115, Issue 10
  • DOI: 10.1021/ja00063a008

Two-Dimensional Polymer Formation on Surfaces: Insight into the Roles of Precursor Mobility and Reactivity
journal, November 2010

  • Bieri, Marco; Nguyen, Manh-Thuong; Gröning, Oliver
  • Journal of the American Chemical Society, Vol. 132, Issue 46
  • DOI: 10.1021/ja107947z

Nucleation and Growth of Covalent Organic Frameworks from Solution: The Example of COF-5
journal, October 2017

  • Li, Haoyuan; Chavez, Anton D.; Li, Huifang
  • Journal of the American Chemical Society, Vol. 139, Issue 45
  • DOI: 10.1021/jacs.7b09169

Synthesis of a Two-Dimensional Covalent Organic Monolayer through Dynamic Imine Chemistry at the Air/Water Interface
journal, November 2015

  • Dai, Wenyang; Shao, Feng; Szczerbiński, Jacek
  • Angewandte Chemie, Vol. 128, Issue 1
  • DOI: 10.1002/ange.201508473

Lyotropic liquid crystallinity in mixed-tautomer Schiff-base macrocycles
journal, January 2015

  • Jiang, Jian; Dong, Ronald Y.; MacLachlan, Mark J.
  • Chemical Communications, Vol. 51, Issue 90
  • DOI: 10.1039/C5CC06253E

Macrocyclic depolymerization of arylene-ethynylene copolymers: a dynamic combinatorial method
journal, January 2012

  • Gross, Dustin E.; Discekici, Emre; Moore, Jeffrey S.
  • Chemical Communications, Vol. 48, Issue 37
  • DOI: 10.1039/c2cc30701d

Mesoporous 2D covalent organic frameworks based on shape-persistent arylene-ethynylene macrocycles
journal, January 2015

  • Yang, Haishen; Du, Ya; Wan, Shun
  • Chemical Science, Vol. 6, Issue 7
  • DOI: 10.1039/C5SC00894H

Physical Basis of Self-Assembly Macrocyclizations
journal, July 1998

  • Ercolani, Gianfranco
  • The Journal of Physical Chemistry B, Vol. 102, Issue 29
  • DOI: 10.1021/jp9816723

Conjugated Macrocycles: Concepts and Applications
journal, September 2011

  • Iyoda, Masahiko; Yamakawa, Jun; Rahman, M. Jalilur
  • Angewandte Chemie International Edition, Vol. 50, Issue 45
  • DOI: 10.1002/anie.201006198

Synthesis and Self-Association of an Imine-Containing m -Phenylene Ethynylene Macrocycle
journal, May 2002

  • Zhao, Dahui; Moore, Jeffrey S.
  • The Journal of Organic Chemistry, Vol. 67, Issue 11
  • DOI: 10.1021/jo010918o

Programmed Dynamic Covalent Assembly of Unsymmetrical Macrocycles
journal, September 2007

  • Hartley, C. Scott; Moore, Jeffrey S.
  • Journal of the American Chemical Society, Vol. 129, Issue 38
  • DOI: 10.1021/ja0745963

Hexagonal Molecular Tiling by Hexagonal Macrocycles at the Liquid/Solid Interface: Structural Effects on Packing Geometry
journal, August 2017


Decoding the Morphological Diversity in Two Dimensional Crystalline Porous Polymers by Core Planarity Modulation
journal, March 2016

  • Halder, Arjun; Kandambeth, Sharath; Biswal, Bishnu P.
  • Angewandte Chemie, Vol. 128, Issue 27
  • DOI: 10.1002/ange.201600087

Cage-templated synthesis of highly stable palladium nanoparticles and their catalytic activities in Suzuki–Miyaura coupling
journal, January 2018

  • Qiu, Li; McCaffrey, Ryan; Jin, Yinghua
  • Chemical Science, Vol. 9, Issue 3
  • DOI: 10.1039/C7SC03148C

The thermodynamics of self-assembly
journal, January 1995

  • Chi, Xianglan; Guerin, Andrea J.; Haycock, Richard A.
  • Journal of the Chemical Society, Chemical Communications, Issue 24
  • DOI: 10.1039/c39950002563

Synthesis of a Two-Dimensional Covalent Organic Monolayer through Dynamic Imine Chemistry at the Air/Water Interface
journal, November 2015

  • Dai, Wenyang; Shao, Feng; Szczerbiński, Jacek
  • Angewandte Chemie International Edition, Vol. 55, Issue 1
  • DOI: 10.1002/anie.201508473

Dynamic Covalent Assembly of Peptoid-Based Ladder Oligomers by Vernier Templating
journal, December 2015

  • Wei, Tao; Jung, Jae Hwan; Scott, Timothy F.
  • Journal of the American Chemical Society, Vol. 137, Issue 51
  • DOI: 10.1021/jacs.5b11251

Enhanced Structural Organization in Covalent Organic Frameworks Through Fluorination
journal, March 2017

  • Alahakoon, Sampath B.; McCandless, Gregory T.; Karunathilake, Arosha A. K.
  • Chemistry - A European Journal, Vol. 23, Issue 18
  • DOI: 10.1002/chem.201700412

Synchronized Offset Stacking: A Concept for Growing Large-Domain and Highly Crystalline 2D Covalent Organic Frameworks
journal, December 2016

  • Auras, Florian; Ascherl, Laura; Hakimioun, Amir H.
  • Journal of the American Chemical Society, Vol. 138, Issue 51
  • DOI: 10.1021/jacs.6b09787

Discrete, Hexagonal Boronate Ester-Linked Macrocycles Related to Two-Dimensional Covalent Organic Frameworks
journal, July 2016


Arylethynyl receptors for neutral molecules and anions: emerging applications in cellular imaging
journal, January 2010

  • Carroll, Calden N.; Naleway, John J.; Haley, Michael M.
  • Chemical Society Reviews, Vol. 39, Issue 10
  • DOI: 10.1039/b926231h

Cyclodepolymerization as a method for the synthesis of macrocyclic oligomers
journal, July 2014


Shape-persistent arylenevinylene macrocycles (AVMs) prepared via acyclic diene metathesis macrocyclization (ADMAC)
journal, January 2009

  • Jin, Yinghua; Zhang, Aibo; Huang, Yongshun
  • Chemical Communications, Vol. 46, Issue 43
  • DOI: 10.1039/c0cc02941f

Relaxing Conformational Constraints in Dynamic Macrocycle Synthesis
journal, June 2014

  • Sisco, Scott W.; Larson, Brandon M.; Moore, Jeffrey S.
  • Macromolecules, Vol. 47, Issue 12
  • DOI: 10.1021/ma500673x

Folding-Driven Reversible Polymerization of Oligo( m -phenylene ethynylene) Imines:  Solvent and Starter Sequence Studies
journal, April 2003

  • Zhao, Dahui; Moore, Jeffrey S.
  • Macromolecules, Vol. 36, Issue 8
  • DOI: 10.1021/ma034159i

A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3]rotaxanes
journal, June 2013

  • Lee, Semin; Chen, Chun-Hsing; Flood, Amar H.
  • Nature Chemistry, Vol. 5, Issue 8
  • DOI: 10.1038/nchem.1668

Arylene–Ethynylene Macrocycles via Depolymerization–Macrocyclization
journal, May 2011

  • Gross, Dustin E.; Moore, Jeffrey S.
  • Macromolecules, Vol. 44, Issue 10
  • DOI: 10.1021/ma2006552