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Title: Poly[n]catenanes: Synthesis of molecular interlocked chains

Abstract

As the macromolecular version of mechanically interlocked molecules, mechanically interlocked polymers are promising candidates for the creation of sophisticated molecular machines and smart soft materials. Poly[n]catenanes, where the molecular chains consist solely of interlocked macrocycles, contain one of the highest concentrations of topological bonds. We report, herein, a synthetic approach toward this distinctive polymer architecture in high yield (similar to 75%) via efficient ring closing of rationally designed metallosupramolecular polymers. Light-scattering, mass spectrometric, and nuclear magnetic resonance characterization of fractionated samples support assignment of the high-molar mass product (number-average molar mass similar to 21.4 kilograms per mole) to a mixture of linear poly[7-26]catenanes, branched poly[13-130]catenanes, and cyclic poly[4-7]catenanes. As a result, increased hydrodynamic radius (in solution) and glass transition temperature (in bulk materials) were observed upon metallation with Zn2+.

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [3];  [4]; ORCiD logo [3]; ORCiD logo [5]
  1. Univ. of Chicago, Chicago, IL (United States); Case Western Reserve Univ., Cleveland, OH (United States)
  2. Univ. of Chicago, Chicago, IL (United States)
  3. Case Western Reserve Univ., Cleveland, OH (United States)
  4. Univ. of Chicago, Chicago, IL (United States); Argonne National Lab. (ANL), Lemont, IL (United States)
  5. Univ. of Chicago, Chicago, IL (United States); Case Western Reserve Univ., Cleveland, OH (United States); Argonne National Lab. (ANL), Lemont, IL (United States)
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
National Science Foundation (NSF); USDOE
OSTI Identifier:
1425221
Grant/Contract Number:  
AC02-06CH11357
Resource Type:
Accepted Manuscript
Journal Name:
Science
Additional Journal Information:
Journal Volume: 358; Journal Issue: 6369; Journal ID: ISSN 0036-8075
Publisher:
AAAS
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Wu, Qiong, Rauscher, Phillip M., Lang, Xiaolong, Wojtecki, Rudy J., de Pablo, Juan J., Hore, Michael J. A., and Rowan, Stuart J. Poly[n]catenanes: Synthesis of molecular interlocked chains. United States: N. p., 2017. Web. doi:10.1126/science.aap7675.
Wu, Qiong, Rauscher, Phillip M., Lang, Xiaolong, Wojtecki, Rudy J., de Pablo, Juan J., Hore, Michael J. A., & Rowan, Stuart J. Poly[n]catenanes: Synthesis of molecular interlocked chains. United States. doi:10.1126/science.aap7675.
Wu, Qiong, Rauscher, Phillip M., Lang, Xiaolong, Wojtecki, Rudy J., de Pablo, Juan J., Hore, Michael J. A., and Rowan, Stuart J. Fri . "Poly[n]catenanes: Synthesis of molecular interlocked chains". United States. doi:10.1126/science.aap7675. https://www.osti.gov/servlets/purl/1425221.
@article{osti_1425221,
title = {Poly[n]catenanes: Synthesis of molecular interlocked chains},
author = {Wu, Qiong and Rauscher, Phillip M. and Lang, Xiaolong and Wojtecki, Rudy J. and de Pablo, Juan J. and Hore, Michael J. A. and Rowan, Stuart J.},
abstractNote = {As the macromolecular version of mechanically interlocked molecules, mechanically interlocked polymers are promising candidates for the creation of sophisticated molecular machines and smart soft materials. Poly[n]catenanes, where the molecular chains consist solely of interlocked macrocycles, contain one of the highest concentrations of topological bonds. We report, herein, a synthetic approach toward this distinctive polymer architecture in high yield (similar to 75%) via efficient ring closing of rationally designed metallosupramolecular polymers. Light-scattering, mass spectrometric, and nuclear magnetic resonance characterization of fractionated samples support assignment of the high-molar mass product (number-average molar mass similar to 21.4 kilograms per mole) to a mixture of linear poly[7-26]catenanes, branched poly[13-130]catenanes, and cyclic poly[4-7]catenanes. As a result, increased hydrodynamic radius (in solution) and glass transition temperature (in bulk materials) were observed upon metallation with Zn2+.},
doi = {10.1126/science.aap7675},
journal = {Science},
number = 6369,
volume = 358,
place = {United States},
year = {2017},
month = {12}
}

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Cited by: 63 works
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Figures / Tables:

Fig. 1 Fig. 1: Conformational mobility and synthetic approach to poly[n]catenane. (A) A robust and flexible metal chain, the macroscopic equivalent of the poly[n]catenane architecture; (B) the common conformational motions observed in catenanes; (C) Comparison of poly[n]catenane and poly[2]catenane; (D) the targeted synthesis of poly[n]catenane 3 via assembling 1 and 2 intomore » a metallo-supramolecular polymer (MSP) followed by ring-closing to yield poly[n]catenate (i.e. metallated poly[n]catenane) and demetallation; and (E) the structure of 1, 2 and 4 (ring-closed product of 1). A few key protons are labeled with blue capital letters in 4 and red lower-case letters in 2. The box highlights the structure of the Bip ligand moiety.« less

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    journal, January 2018

    • Quaglio, Deborah; Zappia, Giovanni; De Paolis, Elisa
    • Organic Chemistry Frontiers, Vol. 5, Issue 20
    • DOI: 10.1039/c8qo00728d

    Can aromaticity be a kinetic trap? Example of mechanically interlocked aromatic [2-5]catenanes built from cyclo[18]carbon
    journal, January 2020

    • Fedik, Nikita; Kulichenko, Maksim; Steglenko, Dmitriy
    • Chemical Communications, Vol. 56, Issue 18
    • DOI: 10.1039/c9cc09483k

    Equilibrium structure and deformation response of 2D kinetoplast sheets
    journal, December 2019

    • Klotz, Alexander R.; Soh, Beatrice W.; Doyle, Patrick S.
    • Proceedings of the National Academy of Sciences, Vol. 117, Issue 1
    • DOI: 10.1073/pnas.1911088116

    Multiply threaded rotaxanes
    journal, February 2018


    Efficient catenane synthesis by cucurbit[6]uril-mediated azide–alkyne cycloaddition
    journal, January 2018

    • Ng, Antony Wing Hung; Yee, Chi-Chung; Wang, Kai
    • Beilstein Journal of Organic Chemistry, Vol. 14
    • DOI: 10.3762/bjoc.14.158

      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.