Skip to main content
OSTI.GOVU.S. Department of Energy Office of Scientific and Technical Information
U.S. Department of Energy
Office of Scientific and Technical Information
 

Single crystals of mechanically entwined helical covalent polymers

Journal Article · · Nature Chemistry
 [1];  [2];  [3];  [4];  [1];  [1];  [1];  [3];  [4];  [4];  [1]
  1. Univ. of Colorado, Boulder, CO (United States)
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
  3. Shanghai Jiao Tong Univ. (China)
  4. Tongji Univ., Shanghai (China)
+ Show Author Affiliations

Double helical conformation of polymer chains is widely observed in biomacromolecules and plays an essential role in exerting their biological functions, such as molecular recognition and information storage. It has remained challenging, however, to prepare synthetic helical polymers, and those that exist have mainly been limited to single-stranded polymers or short oligomeric double helices. In this work, we report the synthesis of covalent helical polymers, with a high molecular weight, from the achiral monomer hexahydroxytriphenylene through to spiroborate formation. Polymerization and crystallization occurred simultaneously under solvothermal conditions to form single crystals of the resulting helical covalent polymers. Characterization by single-crystal X-ray diffraction showed that each crystal consisted of pairs of mechanically entwined polymers. No strong non-covalent interactions were observed between the two helical polymers that formed a pair; instead, each strand interacted with neighbouring pairs through hydrogen bonding. Each individual crystal was made up of helical polymers of the same handedness, but the crystallization process produced a racemic conglomerate, with equal amounts of right-handed and left-handed crystals.

Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC); National Science Foundation of China; Key Project of Basic Research of Shanghai; China Postdoctoral Science Foundation; National Natural Science Foundation of China (NSFC)
Grant/Contract Number:
AC02-05CH11231
OSTI ID:
1838432
Journal Information:
Nature Chemistry, Journal Name: Nature Chemistry Journal Issue: 7 Vol. 13; ISSN 1755-4330
Publisher:
Nature Publishing GroupCopyright Statement
Country of Publication:
United States
Language:
English

References (23)

Self-Assembling Phenylpropyl Ether Dendronized Helical Polyphenylacetylenes journal November 2007
Nanomechanical Function Made Possible by Suppressing Structural Transformations of Polyarylacetylenes journal September 2008
Synthesis, structural, and retrostructural analysis of helical dendronized poly(1-naphthylacetylene)s journal January 2007
Contracted helix to stretched helix Rearrangement of an aromatic polyacetylene prepared in n -hexane with [Rh(norbornadiene)Cl] 2 -triethylamine catalyst journal October 2013
The crystal structure of isotactic poly(methyl methacrylate): packing-mode of double stranded helices journal May 1994
Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions journal October 2016
Synthetic Helical Polymers:  Conformation and Function journal November 2001
Aromatic Amide Foldamers: Structures, Properties, and Functions journal June 2012
Helical Polymers: Synthesis, Structures, and Functions journal November 2009
A Field Guide to Foldamers journal December 2001
Steric Communication of Chiral Information Observed in Dendronized Polyacetylenes journal November 2006
Spiroborate-Based Double-Stranded Helicates: Meso -to- Racemo Isomerization and Ion-Triggered Springlike Motion of the Racemo -Helicate journal November 2018
Self-Organized Columnar Phase of Side-Chain Liquid Crystalline Polymers: To Precisely Control the Number of Chains Bundled in a Supramolecular Column journal August 2014
Molecular Structure of Nucleic Acids: A Structure for Deoxyribose Nucleic Acid journal April 1953
Interconversion of single and double helices formed from synthetic molecular strands journal October 2000
Constructing monocrystalline covalent organic networks by polymerization journal August 2013
Ion-triggered spring-like motion of a double helicate accompanied by anisotropic twisting journal May 2010
Double helical conformation and extreme rigidity in a rodlike polyelectrolyte journal February 2019
Reversible assembly of enantiomeric helical polymers: from fibers to gels journal January 2015
Spontaneous assembly of double-stranded helicates from oligobipyridine ligands and copper(I) cations: structure of an inorganic double helix. journal May 1987
Weaving of organic threads into a crystalline covalent organic framework journal January 2016
Seeded growth of single-crystal two-dimensional covalent organic frameworks journal June 2018
Single-crystal x-ray diffraction structures of covalent organic frameworks journal July 2018

Similar Records

Water-mediated deracemization of a bisporphyrin helicate assisted by diastereoselective encapsulation of chiral guests
Journal Article · Fri Mar 29 00:00:00 EDT 2019 · Nature Communications · OSTI ID:1659567
Metal-Organic Frameworks with Achiral/Monochiral Nano-channels
Journal Article · Fri Jul 01 00:00:00 EDT 2011 · Crystal Growth & Design, 11(7):2824-2828 · OSTI ID:1021834
Coordination polymers assembled from semirigid fluorene-based ligand: A couple of enantiomers
Journal Article · Sat Nov 14 23:00:00 EST 2015 · Journal of Solid State Chemistry · OSTI ID:22573926

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
polymer chemistry
supramolecular chemistry