Poly[n]catenanes: Synthesis of molecular interlocked chains

Wu, Qiong; Rauscher, Phillip M.; Lang, Xiaolong; Wojtecki, Rudy J.; de Pablo, Juan J.; Hore, Michael J. A.; Rowan, Stuart J.

doi:10.1126/science.aap7675

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

Journal Article · Fri Dec 15 00:00:00 EST 2017 · Science

DOI:https://doi.org/10.1126/science.aap7675· OSTI ID:1425221

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Univ. of Chicago, Chicago, IL (United States); Case Western Reserve Univ., Cleveland, OH (United States)
Univ. of Chicago, Chicago, IL (United States)
Case Western Reserve Univ., Cleveland, OH (United States)
Univ. of Chicago, Chicago, IL (United States); Argonne National Lab. (ANL), Lemont, IL (United States)
Univ. of Chicago, Chicago, IL (United States); Case Western Reserve Univ., Cleveland, OH (United States); Argonne National Lab. (ANL), Lemont, IL (United States)

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⁺.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1425221

Journal Information:: Science, Vol. 358, Issue 6369; ISSN 0036-8075

Publisher:: AAASCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 161 works

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References (93)

Enantioselective radical reactions: the use of metal triflimides as Lewis acids Sibi, Mukund P.; Petrovic, Goran Tetrahedron: Asymmetry, Vol. 14, Issue 19 https://doi.org/10.1016/S0957-4166(03)00543-3	journal	October 2003
Force Field Benchmark of Organic Liquids: Density, Enthalpy of Vaporization, Heat Capacities, Surface Tension, Isothermal Compressibility, Volumetric Expansion Coefficient, and Dielectric Constant Caleman, Carl; van Maaren, Paul J.; Hong, Minyan Journal of Chemical Theory and Computation, Vol. 8, Issue 1 https://doi.org/10.1021/ct200731v	journal	December 2011
Discovery of an Organic Trefoil Knot Ponnuswamy, N.; Cougnon, F. B. L.; Clough, J. M. Science, Vol. 338, Issue 6108 https://doi.org/10.1126/science.1227032	journal	November 2012
Application of Static Charge Transfer within an Ionic-Liquid Force Field and Its Effect on Structure and Dynamics Youngs, Tristan G. A.; Hardacre, Christopher ChemPhysChem, Vol. 9, Issue 11 https://doi.org/10.1002/cphc.200800200	journal	August 2008
Static Dielectric Constants of Pure Liquids and Binary Liquid Mixtures Wohlfarth, Christian; Lechner, M. D. Landolt-Börnstein - Group IV Physical Chemistry, Vol. 27 https://doi.org/10.1007/978-3-662-48168-4	book	January 2015
Mechanised nanoparticles for drug delivery Cotí, Karla K.; Belowich, Matthew E.; Liong, Monty Nanoscale, Vol. 1, Issue 1 https://doi.org/10.1039/b9nr00162j	journal	January 2009
A Leap-frog Algorithm for Stochastic Dynamics Van Gunsteren, W. F.; Berendsen, H. J. C. Molecular Simulation, Vol. 1, Issue 3 https://doi.org/10.1080/08927028808080941	journal	March 1988
GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers Abraham, Mark James; Murtola, Teemu; Schulz, Roland SoftwareX, Vol. 1-2 https://doi.org/10.1016/j.softx.2015.06.001	journal	September 2015
Synthesis and Characterization of Poly[2]-catenanes Containing Rigid Catenane Segments Muscat, Dirk; Köhler, Werner; Räder, Hans Joachim Macromolecules, Vol. 32, Issue 6 https://doi.org/10.1021/ma981077z	journal	March 1999
Poly[2]-catenanes containing alternating topological and covalent bonds Weidmann, Jean-Luc; Kern, Jean-Marc; Sauvage, Jean-Pierre Chem. Commun., Issue 10 https://doi.org/10.1039/CC9960001243	journal	January 1996
Zinc binding in proteins and solution: A simple but accurate nonbonded representation Stote, Roland H.; Karplus, Martin Proteins: Structure, Function, and Genetics, Vol. 23, Issue 1 https://doi.org/10.1002/prot.340230104	journal	September 1995
Development of an All-Atom Force Field for Heterocycles. Properties of Liquid Pyrrole, Furan, Diazoles, and Oxazoles McDonald, Nora A.; Jorgensen, William L. The Journal of Physical Chemistry B, Vol. 102, Issue 41 https://doi.org/10.1021/jp981200o	journal	October 1998
Metal–ligand induced supramolecular polymerization: A route to responsive materials Rowan, Stuart J.; Beck, J. Benjamin Faraday Discuss., Vol. 128 https://doi.org/10.1039/b403135k	journal	January 2005
Mechanically Linked Polycarbonate Fustin, Charles-André; Bailly, Christian; Clarkson, Guy J. Journal of the American Chemical Society, Vol. 125, Issue 8 https://doi.org/10.1021/ja0292546	journal	February 2003
Une nouvelle famille de molecules : les metallo-catenanes Dietrich-Buchecker, C. O.; Sauvage, J. P.; Kintzinger, J. P. Tetrahedron Letters, Vol. 24, Issue 46 https://doi.org/10.1016/S0040-4039(00)94050-4	journal	January 1983
Chemical modification of chitosan 11: chitosan–dendrimer hybrid as a tree like molecule Sashiwa, Hitoshi; Shigemasa, Yoshihiro; Roy, Rene Carbohydrate Polymers, Vol. 49, Issue 2 https://doi.org/10.1016/S0144-8617(01)00322-8	journal	August 2002
Bridged Polycatenane Watanabe, Nobuhiro; Ikari, Yoshihiro; Kihara, Nobuhiro Macromolecules, Vol. 37, Issue 18 https://doi.org/10.1021/ma048782u	journal	September 2004
Development of an all-atom force field for heterocycles. Properties of liquid pyridine and diazenes Jorgensen, William L.; McDonald, Nora A. Journal of Molecular Structure: THEOCHEM, Vol. 424, Issue 1-2 https://doi.org/10.1016/S0166-1280(97)00237-6	journal	February 1998
Artificial Molecular Machines Erbas-Cakmak, Sundus; Leigh, David A.; McTernan, Charlie T. Chemical Reviews, Vol. 115, Issue 18 https://doi.org/10.1021/acs.chemrev.5b00146	journal	August 2015
PRODRG : a tool for high-throughput crystallography of protein–ligand complexes Schüttelkopf, Alexander W.; van Aalten, Daan M. F. Acta Crystallographica Section D Biological Crystallography, Vol. 60, Issue 8 https://doi.org/10.1107/S0907444904011679	journal	July 2004
Substituent- and Solvent-Effects on the Stability of Iron(Ii)-4-X-2,6-Bis-(Benzimidazol-2′-Yl)Pyridine Complexes Showing Spin-Crossover in Solution Enamullah, M.; Linert, W. Journal of Coordination Chemistry, Vol. 40, Issue 3 https://doi.org/10.1080/00958979608024344	journal	December 1996
Canonical sampling through velocity rescaling Bussi, Giovanni; Donadio, Davide; Parrinello, Michele The Journal of Chemical Physics, Vol. 126, Issue 1 https://doi.org/10.1063/1.2408420	journal	January 2007
GROMACS: A message-passing parallel molecular dynamics implementation Berendsen, H. J. C.; van der Spoel, D.; van Drunen, R. Computer Physics Communications, Vol. 91, Issue 1-3 https://doi.org/10.1016/0010-4655(95)00042-E	journal	September 1995
Charge-Scaling Effect in Ionic Liquids from the Charge-Density Analysis of N , N′ -Dimethylimidazolium Methylsulfate Beichel, Witali; Trapp, Nils; Hauf, Christoph Angewandte Chemie International Edition, Vol. 53, Issue 12 https://doi.org/10.1002/anie.201308760	journal	February 2014
Particle mesh Ewald: An N ⋅log( N ) method for Ewald sums in large systems Darden, Tom; York, Darrin; Pedersen, Lee The Journal of Chemical Physics, Vol. 98, Issue 12 https://doi.org/10.1063/1.464397	journal	June 1993
Molecular dynamics with coupling to an external bath Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F. The Journal of Chemical Physics, Vol. 81, Issue 8 https://doi.org/10.1063/1.448118	journal	October 1984
Density and viscosity of ethanol + 1,2-dichloroethane, ethanol + 1,1,1-trichloroethane, and ethanol + 1,1,2,2-tetrachloroethane binary mixtures Sivaramprasad, G.; Rao, M. Venkateshwara; Prasad, D. H. L. Journal of Chemical & Engineering Data, Vol. 35, Issue 2 https://doi.org/10.1021/je00060a006	journal	April 1990
System-Size Dependence of Diffusion Coefficients and Viscosities from Molecular Dynamics Simulations with Periodic Boundary Conditions Yeh, In-Chul; Hummer, Gerhard The Journal of Physical Chemistry B, Vol. 108, Issue 40 https://doi.org/10.1021/jp0477147	journal	October 2004
Rational identification and characterisation of peptide ligands for targeting polysialic acid Shastry, Divya G.; Irudayanathan, Flaviyan Jerome; Williams, Asher Scientific Reports, Vol. 10, Issue 1 https://doi.org/10.1038/s41598-020-64088-z	journal	May 2020
Catenated Poly(ε-caprolactone) and Poly( l -lactide) via Ring-Expansion Strategy Cao, Peng-Fei; Mangadlao, Joey Dacula; de Leon, Al Macromolecules, Vol. 48, Issue 12 https://doi.org/10.1021/acs.macromol.5b00470	journal	June 2015
Polymorphic transitions in single crystals: A new molecular dynamics method Parrinello, M.; Rahman, A. Journal of Applied Physics, Vol. 52, Issue 12 https://doi.org/10.1063/1.328693	journal	December 1981
Structure of Erm-modified 70S ribosome reveals the mechanism of macrolide resistance Svetlov, Maxim S.; Syroegin, Egor A.; Aleksandrova, Elena V. Nature Chemical Biology, Vol. 17, Issue 4 https://doi.org/10.1038/s41589-020-00715-0	journal	January 2021
Influence of a Single Catenane on the Solid-State Properties of Mechanically Linked Polymers Ahamed, B. Nisar; Van Velthem, Pascal; Robeyns, Koen ACS Macro Letters, Vol. 6, Issue 4 https://doi.org/10.1021/acsmacrolett.7b00204	journal	April 2017
GROMACS molecule & liquid database van der Spoel, D.; van Maaren, P. J.; Caleman, C. Bioinformatics, Vol. 28, Issue 5 https://doi.org/10.1093/bioinformatics/bts020	journal	January 2012
Enhancing Cation Diffusion and Suppressing Anion Diffusion via Lewis-Acidic Polymer Electrolytes Savoie, Brett M.; Webb, Michael A.; Miller, Thomas F. The Journal of Physical Chemistry Letters, Vol. 8, Issue 3 https://doi.org/10.1021/acs.jpclett.6b02662	journal	January 2017
Olympiadane Amabilino, David B.; Ashton, Peter R.; Reder, Anatoli S. Angewandte Chemie International Edition in English, Vol. 33, Issue 12 https://doi.org/10.1002/anie.199412861	journal	June 1994
Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands McKenzie, Blayne M.; Miller, Adriane K.; Wojtecki, Rudy J. Tetrahedron, Vol. 64, Issue 36 https://doi.org/10.1016/j.tet.2008.05.075	journal	September 2008
Computer Simulation of Molecular Dynamics: Methodology, Applications, and Perspectives in Chemistry van Gunsteren, Wilfred F.; Berendsen, Herman J. C. Angewandte Chemie International Edition in English, Vol. 29, Issue 9 https://doi.org/10.1002/anie.199009921	journal	September 1990
Metallo-, Thermo-, and Photoresponsive Shape Memory and Actuating Liquid Crystalline Elastomers Michal, Brian T.; McKenzie, Blayne M.; Felder, Simcha E. Macromolecules, Vol. 48, Issue 10 https://doi.org/10.1021/acs.macromol.5b00646	journal	May 2015
Improving the specificity of organophosphorus hydrolase to acephate by mutagenesis at its binding site: a computational study Badakhshan, Reza; Mohammadi, Mozafar; Farnoosh, Gholamreza Journal of Molecular Modeling, Vol. 27, Issue 6 https://doi.org/10.1007/s00894-021-04749-6	journal	May 2021
Computer Simulation of Liquids Allen, M. P.; Tildesley, D. J.; Banavar, Jayanth R. Physics Today, Vol. 42, Issue 3 https://doi.org/10.1063/1.2810937	journal	March 1989
VMD: Visual molecular dynamics Humphrey, William; Dalke, Andrew; Schulten, Klaus Journal of Molecular Graphics, Vol. 14, Issue 1 https://doi.org/10.1016/0263-7855(96)00018-5	journal	February 1996
A [2] Catenane Made to Order Ashton, Peter R.; Goodnow, Timothy T.; Kaifer, Angel E. Angewandte Chemie International Edition in English, Vol. 28, Issue 10 https://doi.org/10.1002/anie.198913961	journal	October 1989
Stiff Chains and Filaments under Tension Odijk, Theo Macromolecules, Vol. 28, Issue 20 https://doi.org/10.1021/ma00124a044	journal	September 1995
Does decreasing ion–ion association improve cation mobility in single ion conductors? Lin, Kan-Ju; Maranas, Janna K. Physical Chemistry Chemical Physics, Vol. 15, Issue 38 https://doi.org/10.1039/c3cp51661j	journal	January 2013
From topological gels to slide-ring materials: Review Noda, Yumiki; Hayashi, Yuki; Ito, Kohzo Journal of Applied Polymer Science, Vol. 131, Issue 15 https://doi.org/10.1002/app.40509	journal	February 2014
Mechanically interlocked and switchable molecules at surfaces Davis, Jason J.; Orlowski, Grzegorz A.; Rahman, Habibur Chem. Commun., Vol. 46, Issue 1 https://doi.org/10.1039/B915122B	journal	January 2010
Artificial molecular machines Guterres, Mariana F. A. N.; Ronconi, Célia M. Revista Virtual de Química, Vol. 1, Issue 2 https://doi.org/10.5935/1984-6835.20090013	journal	January 2009
Using the dynamic bond to access macroscopically responsive structurally dynamic polymers Wojtecki, Rudy J.; Meador, Michael A.; Rowan, Stuart J. Nature Materials, Vol. 10, Issue 1 https://doi.org/10.1038/nmat2891	journal	December 2010
P-LINCS: A Parallel Linear Constraint Solver for Molecular Simulation Hess, Berk Journal of Chemical Theory and Computation, Vol. 4, Issue 1 https://doi.org/10.1021/ct700200b	journal	December 2007
Molecular Dynamics Studies of Polyethylene Oxide and Polyethylene Glycol: Hydrodynamic Radius and Shape Anisotropy Lee, Hwankyu; Venable, Richard M.; MacKerell, Alexander D. Biophysical Journal, Vol. 95, Issue 4 https://doi.org/10.1529/biophysj.108.133025	journal	August 2008
Ring-Opening Metathesis Polymerization of a Diolefinic [2]-Catenane–Copper(I) Complex: An Easy Route to Polycatenanes Berrocal, José Augusto; Pitet, Louis M.; Nieuwenhuizen, Marko M. L. Macromolecules, Vol. 48, Issue 5 https://doi.org/10.1021/ma502392v	journal	February 2015
Light scattering and the absolute characterization of macromolecules Wyatt, Philip J. Analytica Chimica Acta, Vol. 272, Issue 1 https://doi.org/10.1016/0003-2670(93)80373-S	journal	February 1993
Electron affinities of the first‐row atoms revisited. Systematic basis sets and wave functions Kendall, Rick A.; Dunning, Thom H.; Harrison, Robert J. The Journal of Chemical Physics, Vol. 96, Issue 9 https://doi.org/10.1063/1.462569	journal	May 1992
Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions Krishnan, R.; Binkley, J. S.; Seeger, R. The Journal of Chemical Physics, Vol. 72, Issue 1 https://doi.org/10.1063/1.438955	journal	January 1980
Metal Ion Modeling Using Classical Mechanics Li, Pengfei; Merz, Kenneth M. Chemical Reviews, Vol. 117, Issue 3 https://doi.org/10.1021/acs.chemrev.6b00440	journal	January 2017
Enantioselective Radical Reactions: The Use of Metal Triflimides as Lewis Acids. Sibi, Mukund P.; Petrovic, Goran ChemInform, Vol. 35, Issue 6 https://doi.org/10.1002/chin.200406025	journal	February 2004
Computer simulation of a polymer electrolyte: Lithium iodide in amorphous poly(ethylene oxide) Müller‐Plathe, Florian; van Gunsteren, Wilfred F. The Journal of Chemical Physics, Vol. 103, Issue 11 https://doi.org/10.1063/1.470611	journal	September 1995
Molecular Borromean Rings Chichak, K. S. Science, Vol. 304, Issue 5675 https://doi.org/10.1126/science.1096914	journal	May 2004
Epoxidation of polybutadiene by a topologically linked catalyst Thordarson, Pall; Bijsterveld, Edward J. A.; Rowan, Alan E. Nature, Vol. 424, Issue 6951 https://doi.org/10.1038/nature01925	journal	August 2003
Polycatenanes Niu, Zhenbin; Gibson, Harry W. Chemical Reviews, Vol. 109, Issue 11 https://doi.org/10.1021/cr900002h	journal	November 2009
Self-recognition in helicate self-assembly: spontaneous formation of helical metal complexes from mixtures of ligands and metal ions. Kramer, R.; Lehn, J. M.; Marquis-Rigault, A. Proceedings of the National Academy of Sciences, Vol. 90, Issue 12 https://doi.org/10.1073/pnas.90.12.5394	journal	June 1993
Ionic Charge Reduction and Atomic Partial Charges from First-Principles Calculations of 1,3-Dimethylimidazolium Chloride Schmidt, Jochen; Krekeler, Christian; Dommert, Florian The Journal of Physical Chemistry B, Vol. 114, Issue 18 https://doi.org/10.1021/jp910771q	journal	May 2010
Stretching DNA with optical tweezers Wang, M. D.; Yin, H.; Landick, R. Biophysical Journal, Vol. 72, Issue 3 https://doi.org/10.1016/S0006-3495(97)78780-0	journal	March 1997
Optically healable supramolecular polymers Burnworth, Mark; Tang, Liming; Kumpfer, Justin R. Nature, Vol. 472, Issue 7343, p. 334-337 https://doi.org/10.1038/nature09963	journal	April 2011
Optimizing the formation of 2,6-bis(N-alkyl-benzimidazolyl)pyridine-containing [3]catenates through component design Wojtecki, Rudy J.; Wu, Qiong; Johnson, J. Casey Chemical Science, Vol. 4, Issue 12 https://doi.org/10.1039/c3sc52082j	journal	January 2013
A molecular dynamics method for simulations in the canonical ensemble NosÉ, SH[Ubar]ICHI Molecular Physics, Vol. 100, Issue 1 https://doi.org/10.1080/00268970110089108	journal	January 2002
A molecular dynamics method for simulations in the canonical ensemble Nosé, Shūichi Molecular Physics, Vol. 52, Issue 2 https://doi.org/10.1080/00268978400101201	journal	June 1984
Macrocycle Size Matters: “Small” Functionalized Rotaxanes in Excellent Yield Using the CuAAC Active Template Approach Lahlali, Hicham; Jobe, Kajally; Watkinson, Michael Angewandte Chemie, Vol. 123, Issue 18 https://doi.org/10.1002/ange.201100415	journal	April 2011
Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids Jorgensen, William L.; Maxwell, David S.; Tirado-Rives, Julian Journal of the American Chemical Society, Vol. 118, Issue 45 https://doi.org/10.1021/ja9621760	journal	January 1996
Estimating Error in Diffusion Coefficients Derived from Molecular Dynamics Simulations Pranami, Gaurav; Lamm, Monica H. Journal of Chemical Theory and Computation, Vol. 11, Issue 10 https://doi.org/10.1021/acs.jctc.5b00574	journal	September 2015
Supramolecular topology Breault, Gloria A.; Hunter, Christopher A.; Mayers, Paul C. Tetrahedron, Vol. 55, Issue 17 https://doi.org/10.1016/S0040-4020(99)00282-3	journal	April 1999
Braiding a molecular knot with eight crossings Danon, Jonathan J.; Krüger, Anneke; Leigh, David A. Science, Vol. 355, Issue 6321 https://doi.org/10.1126/science.aal1619	journal	January 2017
Synthesis of linear [5]catenanes via olefin metathesis dimerization of pseudorotaxanes composed of a [2]catenane and a secondary ammonium salt Iwamoto, Hajime; Tafuku, Shinji; Sato, Yoshihiko Chemical Communications, Vol. 52, Issue 2 https://doi.org/10.1039/C5CC07562A	journal	January 2016
The Five-Stage Self-Assembly of a Branched Heptacatenane Amabilino, David B.; Ashton, Peter R.; Boyd, Sue E. Angewandte Chemie International Edition in English, Vol. 36, Issue 19 https://doi.org/10.1002/anie.199720701	journal	October 1997
Potential energy functions for atomic-level simulations of water and organic and biomolecular systems Jorgensen, W. L.; Tirado-Rives, J. Proceedings of the National Academy of Sciences, Vol. 102, Issue 19 https://doi.org/10.1073/pnas.0408037102	journal	May 2005
Simulation of Single Complex Macromolecules. 1. Structure and Dynamics of Catenanes Pakula, T.; Jeszka, K. Macromolecules, Vol. 32, Issue 20 https://doi.org/10.1021/ma990248c	journal	October 1999
An "Endless" Route to Cyclic Polymers Bielawski, Christopher W.; Benitez, Diego; Grubbs, Robert H. Science, Vol. 297, Issue 5589, p. 2041-2044 https://doi.org/10.1126/science.1075401	journal	September 2002
Canonical dynamics: Equilibrium phase-space distributions Hoover, William G. Physical Review A, Vol. 31, Issue 3 https://doi.org/10.1103/PhysRevA.31.1695	journal	March 1985
Synthesis and Characterization of Poly(1,2-dithiane) Endo, Kiyoshi; Shiroi, Tomotsugu; Murata, Naoki Macromolecules, Vol. 37, Issue 9 https://doi.org/10.1021/ma021237d	journal	May 2004
Macrocycle Size Matters: “Small” Functionalized Rotaxanes in Excellent Yield Using the CuAAC Active Template Approach Lahlali, Hicham; Jobe, Kajally; Watkinson, Michael Angewandte Chemie International Edition, Vol. 50, Issue 18 https://doi.org/10.1002/anie.201100415	journal	April 2011
Properties and emerging applications of mechanically interlocked ligands Lewis, James E. M.; Galli, Marzia; Goldup, Stephen M. Chemical Communications, Vol. 53, Issue 2 https://doi.org/10.1039/C6CC07377H	journal	January 2017
A smooth particle mesh Ewald method Essmann, Ulrich; Perera, Lalith; Berkowitz, Max L. The Journal of Chemical Physics, Vol. 103, Issue 19 https://doi.org/10.1063/1.470117	journal	November 1995
Transverse-current autocorrelation-function calculations of the shear viscosity for molecular liquids Palmer, Bruce J. Physical Review E, Vol. 49, Issue 1 https://doi.org/10.1103/PhysRevE.49.359	journal	January 1994
Characterization of Biaryl Torsional Energetics and its Treatment in OPLS All-Atom Force Fields Dahlgren, Markus K.; Schyman, Patric; Tirado-Rives, Julian Journal of Chemical Information and Modeling, Vol. 53, Issue 5 https://doi.org/10.1021/ci4001597	journal	April 2013
Thermo-, Photo-, and Chemo-Responsive Shape-Memory Properties from Photo-Cross-Linked Metallo-Supramolecular Polymers Kumpfer, Justin R.; Rowan, Stuart J. Journal of the American Chemical Society, Vol. 133, Issue 32 https://doi.org/10.1021/ja205332w	journal	August 2011
Bis[2,6-bis(1-methyl-1 H -benzimidazol-2-yl-κ N ³ )pyridine-κ N ]zinc dipicrate methanol disolvate Fan, Xuyang; Yuan, Jingkun; Bai, Ying Acta Crystallographica Section E Structure Reports Online, Vol. 68, Issue 8 https://doi.org/10.1107/S1600536812031443	journal	July 2012
Artificial Molecular Machines Balzani, Vincenzo; Credi, Alberto; Raymo, Françisco M. Angewandte Chemie, Vol. 39, Issue 19 https://doi.org/10.1002/1521-3773(20001002)39:19<3348::aid-anie3348>3.0.co;2-x	journal	October 2000
Poly[2]catenanes and Cyclic Oligo[2]catenanes Containing Alternating Topological and Covalent Bonds: Synthesis and Characterization Weidmann, Jean-Luc; Kern, Jean-Marc; Sauvage, Jean-Pierre Chemistry - A European Journal, Vol. 5, Issue 6 https://doi.org/10.1002/(SICI)1521-3765(19990604)5:6<1841::AID-CHEM1841>3.0.CO;2-Q	journal	June 1999
Main-Chain and Pendant Poly([2]catenane)s Incorporating Complementary π-Electron-Rich and -Deficient Components Hamers, Christoph; Raymo, Françisco M.; Stoddart, J. Fraser European Journal of Organic Chemistry, Vol. 1998, Issue 10 https://doi.org/10.1002/(SICI)1099-0690(199810)1998:10<2109::AID-EJOC2109>3.0.CO;2-M	journal	October 1998
A Poly(bis[2]catenane) Containing a Combination of Covalent, Mechanical, and Coordinative Bonds Hamers, Christoph; Kocian, Oldrich; Raymo, Françisco M. Advanced Materials, Vol. 10, Issue 16 https://doi.org/10.1002/(SICI)1521-4095(199811)10:16<1366::AID-ADMA1366>3.0.CO;2-D	journal	November 1998
LINCS: A linear constraint solver for molecular simulations Hess, Berk; Bekker, Henk; Berendsen, Herman J. C. Journal of Computational Chemistry, Vol. 18, Issue 12 https://doi.org/10.1002/(SICI)1096-987X(199709)18:12<1463::AID-JCC4>3.0.CO;2-H	journal	September 1997
Charge-Scaling Effect in Ionic Liquids from the Charge-Density Analysis of N , N′ -Dimethylimidazolium Methylsulfate Beichel, Witali; Trapp, Nils; Hauf, Christoph Angewandte Chemie, Vol. 126, Issue 12 https://doi.org/10.1002/ange.201308760	journal	February 2014

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Equilibrium structure and deformation response of 2D kinetoplast sheets Klotz, Alexander R.; Soh, Beatrice W.; Doyle, Patrick S. Proceedings of the National Academy of Sciences, Vol. 117, Issue 1 https://doi.org/10.1073/pnas.1911088116	journal	December 2019
Programming permanent and transient molecular protection via mechanical stoppering Soto, Miguel A.; Lelj, Francesco; MacLachlan, Mark J. Chemical Science, Vol. 10, Issue 44 https://doi.org/10.1039/c9sc03744f	journal	January 2019
A Functioning Macroscopic “Rubik's Cube” Assembled via Controllable Dynamic Covalent Interactions Ji, Xiaofan; Li, Zhao; Liu, Xiaolin Advanced Materials, Vol. 31, Issue 40 https://doi.org/10.1002/adma.201902365	journal	August 2019
Efficient catenane synthesis by cucurbit[6]uril-mediated azide–alkyne cycloaddition Ng, Antony Wing Hung; Yee, Chi-Chung; Wang, Kai Beilstein Journal of Organic Chemistry, Vol. 14 https://doi.org/10.3762/bjoc.14.158	journal	January 2018
Supermacrocyclic Assemblies by Hydrogen-Bond Codes of C7-Phenol Pyrazolo and Pyrrolo Derivatives of Adenine Chai, Yingying; Zhou, Xinglong; Li, Changfu Chemistry - A European Journal, Vol. 24, Issue 58 https://doi.org/10.1002/chem.201803429	journal	September 2018
Vapour-driven crystal-to-crystal transformation showing an interlocking switch of the coordination polymer chains between 1D and 3D Sun, Li; Guo, Rui-Yun; Yang, Xiao-Dong CrystEngComm, Vol. 20, Issue 24 https://doi.org/10.1039/c8ce00591e	journal	January 2018
Multiply threaded rotaxanes McGonigal, Paul R. Supramolecular Chemistry, Vol. 30, Issue 9 https://doi.org/10.1080/10610278.2018.1433832	journal	February 2018
Polymernetzwerke: Von Kunststoffen und Gelen zu porösen Gerüsten Gu, Yuwei; Zhao, Julia; Johnson, Jeremiah A. Angewandte Chemie, Vol. 132, Issue 13 https://doi.org/10.1002/ange.201902900	journal	January 2020
A cyclic bis[2]catenane metallacage Wang, Yiliang; Zhang, Yicheng; Zhou, Zhixuan Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-16556-3	journal	June 2020
Self-templated synthesis of amide catenanes and formation of a catenane coordination polymer Lewis, James E. M. Organic & Biomolecular Chemistry, Vol. 17, Issue 9 https://doi.org/10.1039/c9ob00107g	journal	January 2019
Olefin metathesis reaction as a locking tool for macrocycle and mechanomolecule construction Quaglio, Deborah; Zappia, Giovanni; De Paolis, Elisa Organic Chemistry Frontiers, Vol. 5, Issue 20 https://doi.org/10.1039/c8qo00728d	journal	January 2018
Polymer Networks: From Plastics and Gels to Porous Frameworks Gu, Yuwei; Zhao, Julia; Johnson, Jeremiah A. Angewandte Chemie International Edition, Vol. 59, Issue 13 https://doi.org/10.1002/anie.201902900	journal	March 2020
One-pot synthesis of cyclodextrin-based radial poly[n]catenanes Higashi, Taishi; Morita, Kentaro; Song, Xia Communications Chemistry, Vol. 2, Issue 1 https://doi.org/10.1038/s42004-019-0180-x	journal	July 2019
Supramolekulare Metallopolymere: Von linearen Materialien zu infiniten Netzwerken Bentz, Kyle C.; Cohen, Seth M. Angewandte Chemie, Vol. 130, Issue 46 https://doi.org/10.1002/ange.201806912	journal	October 2018
Supramolecular Metallopolymers: From Linear Materials to Infinite Networks Bentz, Kyle C.; Cohen, Seth M. Angewandte Chemie International Edition, Vol. 57, Issue 46 https://doi.org/10.1002/anie.201806912	journal	October 2018
Synthesis of Terpyridine-Terminated Amphiphilic Block Copolymers and Their Self-Assembly into Metallo-Polymer Nanovesicles Elkin, Tatyana; Copp, Stacy; Hamblin, Ryan Materials, Vol. 12, Issue 4 https://doi.org/10.3390/ma12040601	journal	February 2019