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<a class="vector-toc-link" href="#Mechanical_bonding_effects_on_non-covalent_interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Mechanical bonding effects on non-covalent interactions</span> </div> </a> <ul id="toc-Mechanical_bonding_effects_on_non-covalent_interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanical_bonding_effects_on_chemical_reactivity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mechanical_bonding_effects_on_chemical_reactivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Mechanical bonding effects on chemical reactivity</span> </div> </a> <ul id="toc-Mechanical_bonding_effects_on_chemical_reactivity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications_of_mechanical_bonding_in_controlling_chemical_reactivity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Applications_of_mechanical_bonding_in_controlling_chemical_reactivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Applications of mechanical bonding in controlling chemical reactivity</span> </div> </a> <ul id="toc-Applications_of_mechanical_bonding_in_controlling_chemical_reactivity-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Examples" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Examples"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Examples</span> </div> </a> <ul id="toc-Examples-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" 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class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Molecules connected due to their topology</div> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, <b>mechanically interlocked molecular architectures</b> (<b>MIMAs</b>) are <a href="/wiki/Molecule" title="Molecule">molecules</a> that are connected as a consequence of their <a href="/wiki/Topology_(chemistry)" title="Topology (chemistry)">topology</a>. This connection of molecules is analogous to keys on a <a href="/wiki/Keychain" title="Keychain">keychain</a> loop. The keys are not directly connected to the keychain loop but they cannot be separated without breaking the loop. On the molecular level, the interlocked molecules cannot be separated without the breaking of the <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bonds</a> that comprise the conjoined molecules; this is referred to as a <b>mechanical bond</b>. Examples of mechanically interlocked molecular architectures include <a href="/wiki/Catenane" title="Catenane">catenanes</a>, <a href="/wiki/Rotaxane" title="Rotaxane">rotaxanes</a>, <a href="/wiki/Molecular_knot" title="Molecular knot">molecular knots</a>, and <a href="/wiki/Molecular_Borromean_rings" title="Molecular Borromean rings">molecular Borromean rings</a>. Work in this area was recognized with the 2016 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> to <a href="/wiki/Bernard_L._Feringa" class="mw-redirect" title="Bernard L. Feringa">Bernard L. Feringa</a>, <a href="/wiki/Jean-Pierre_Sauvage" title="Jean-Pierre Sauvage">Jean-Pierre Sauvage</a>, and <a href="/wiki/J._Fraser_Stoddart" class="mw-redirect" title="J. Fraser Stoddart">J. Fraser Stoddart</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>The synthesis of such entangled architectures has been made efficient by combining <a href="/wiki/Supramolecular_chemistry" title="Supramolecular chemistry">supramolecular chemistry</a> with traditional covalent synthesis, however mechanically interlocked molecular architectures have properties that differ from both "<a href="/wiki/Supramolecular_assembly" class="mw-redirect" title="Supramolecular assembly">supramolecular assemblies</a>" and "covalently bonded molecules". The terminology "mechanical bond" has been coined to describe the connection between the components of mechanically interlocked molecular architectures. Although research into mechanically interlocked molecular architectures is primarily focused on artificial compounds, many examples have been found in biological systems including: <a href="/wiki/Cystine_knot" title="Cystine knot">cystine knots</a>, <a href="/wiki/Cyclotide" title="Cyclotide">cyclotides</a> or lasso-peptides such as <a href="/wiki/Microcin" title="Microcin">microcin</a> J25 which are <a href="/wiki/Protein" title="Protein">proteins</a>, and a variety of <a href="/wiki/Peptide" title="Peptide">peptides</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Residual_topology">Residual topology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mechanically_interlocked_molecular_architectures&action=edit&section=1" title="Edit section: Residual topology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><b>Residual topology</b> <sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> is a descriptive <a href="/wiki/Stereochemical" class="mw-redirect" title="Stereochemical">stereochemical</a> term to classify a number of intertwined and interlocked molecules, which cannot be disentangled in an experiment without breaking of <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bonds</a>, while the strict rules of mathematical <a href="/wiki/Topology" title="Topology">topology</a> allow such a disentanglement. Examples of such molecules are <a href="/wiki/Rotaxane" title="Rotaxane">rotaxanes</a>, <a href="/wiki/Catenane" title="Catenane">catenanes</a> with covalently linked rings (so-called <a href="/w/index.php?title=Pretzelane&action=edit&redlink=1" class="new" title="Pretzelane (page does not exist)">pretzelanes</a>), and open knots (pseudoknots) which are abundant in <a href="/wiki/Protein" title="Protein">proteins</a>. </p><p>The term "residual topology" was suggested on account of a striking similarity of these compounds to the well-established topologically nontrivial species, such as catenanes and <a href="/wiki/Knotane" class="mw-redirect" title="Knotane">knotanes</a> (molecular knots). The idea of residual topological isomerism introduces a handy scheme of modifying the <a href="/wiki/Molecular_graph" title="Molecular graph">molecular graphs</a> and generalizes former efforts of systemization of mechanically bound and bridged molecules. </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mechanically_interlocked_molecular_architectures&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Experimentally the first examples of mechanically interlocked molecular architectures appeared in the 1960s with catenanes being synthesized by Wasserman and Schill and rotaxanes by Harrison and Harrison. The chemistry of MIMAs came of age when Sauvage pioneered their synthesis using templating methods.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In the early 1990s the usefulness and even the existence of MIMAs were challenged. The latter concern was addressed by X ray crystallographer and structural chemist David Williams. Two postdoctoral researchers who took on the challenge of producing [5]catenane (olympiadane) pushed the boundaries of the complexity of MIMAs that could be synthesized their success was confirmed in 1996 by a solid‐state structure analysis conducted by David Williams.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanical_bonding_and_chemical_reactivity">Mechanical bonding and chemical reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mechanically_interlocked_molecular_architectures&action=edit&section=3" title="Edit section: Mechanical bonding and chemical reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The introduction of a mechanical bond alters the chemistry of the sub components of rotaxanes and catenanes. <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">Steric hindrance</a> of reactive functionalities is increased and the strength of <a href="/wiki/Non-covalent_interactions" class="mw-redirect" title="Non-covalent interactions">non-covalent interactions</a> between the components are altered.<sup id="cite_ref-:02_8-0" class="reference"><a href="#cite_note-:02-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Mechanical_bonding_effects_on_non-covalent_interactions">Mechanical bonding effects on non-covalent interactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mechanically_interlocked_molecular_architectures&action=edit&section=4" title="Edit section: Mechanical bonding effects on non-covalent interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The strength of non-covalent interactions in a mechanically interlocked molecular architecture increases as compared to the non-mechanically bonded analogues. This increased strength is demonstrated by the necessity of harsher conditions to remove a metal template ion from catenanes as opposed to their non-mechanically bonded analogues. This effect is referred to as the "catenand effect".<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The augmented non-covalent interactions in interlocked systems compared to non-interlocked systems has found utility in the strong and selective binding of a range of charged species, enabling the development of interlocked systems for the extraction of a range of salts.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> This increase in strength of non-covalent interactions is attributed to the loss of <a href="/wiki/Degrees_of_freedom_(physics_and_chemistry)" title="Degrees of freedom (physics and chemistry)">degrees of freedom</a> upon the formation of a mechanical bond. The increase in strength of non-covalent interactions is more pronounced on smaller interlocked systems, where more degrees of freedom are lost, as compared to larger mechanically interlocked systems where the change in degrees of freedom is lower. Therefore, if the ring in a rotaxane is made smaller the strength of non-covalent interactions increases, the same effect is observed if the thread is made smaller as well.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Mechanical_bonding_effects_on_chemical_reactivity">Mechanical bonding effects on chemical reactivity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mechanically_interlocked_molecular_architectures&action=edit&section=5" title="Edit section: Mechanical bonding effects on chemical reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The mechanical bond can reduce the kinetic reactivity of the products, this is ascribed to the increased steric hindrance. Because of this effect <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> of an alkene on the thread of a rotaxane is significantly slower as compared to the equivalent non interlocked thread.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> This effect has allowed for the isolation of otherwise reactive intermediates. </p><p>The ability to alter reactivity without altering covalent structure has led to MIMAs being investigated for a number of technological applications. </p> <div class="mw-heading mw-heading3"><h3 id="Applications_of_mechanical_bonding_in_controlling_chemical_reactivity">Applications of mechanical bonding in controlling chemical reactivity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mechanically_interlocked_molecular_architectures&action=edit&section=6" title="Edit section: Applications of mechanical bonding in controlling chemical reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The ability for a mechanical bond to reduce reactivity and hence prevent unwanted reactions has been exploited in a number of areas. One of the earliest applications was in the protection of <a href="/wiki/Organic_dye" class="mw-redirect" title="Organic dye">organic dyes</a> from <a href="/wiki/Industrial_dye_degradation" title="Industrial dye degradation">environmental degradation</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mechanically_interlocked_molecular_architectures&action=edit&section=7" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Olympiadane" title="Olympiadane">Olympiadane</a></li></ul> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Rotaxane_cartoon.jpg" class="mw-file-description" title="Rotaxane"><img alt="Rotaxane" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Rotaxane_cartoon.jpg/120px-Rotaxane_cartoon.jpg" decoding="async" width="120" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Rotaxane_cartoon.jpg/180px-Rotaxane_cartoon.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Rotaxane_cartoon.jpg/240px-Rotaxane_cartoon.jpg 2x" data-file-width="361" data-file-height="242" /></a></span></div> <div class="gallerytext"><a href="/wiki/Rotaxane" title="Rotaxane">Rotaxane</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:CatenaneScheme.svg" class="mw-file-description" title="Catenane"><img alt="Catenane" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/CatenaneScheme.svg/120px-CatenaneScheme.svg.png" decoding="async" width="120" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/CatenaneScheme.svg/180px-CatenaneScheme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/CatenaneScheme.svg/240px-CatenaneScheme.svg.png 2x" data-file-width="155" data-file-height="130" /></a></span></div> <div class="gallerytext"><a href="/wiki/Catenane" title="Catenane">Catenane</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Trefoil_knot_arb.png" class="mw-file-description" title="Molecular knot"><img alt="Molecular knot" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Trefoil_knot_arb.png/120px-Trefoil_knot_arb.png" decoding="async" width="120" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Trefoil_knot_arb.png/180px-Trefoil_knot_arb.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/Trefoil_knot_arb.png/240px-Trefoil_knot_arb.png 2x" data-file-width="1024" data-file-height="768" /></a></span></div> <div class="gallerytext"><a href="/wiki/Molecular_knot" title="Molecular knot">Molecular knot</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Molecular_Borromean_Ring.png" class="mw-file-description" title="Molecular Borromean rings"><img alt="Molecular Borromean rings" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Molecular_Borromean_Ring.png/120px-Molecular_Borromean_Ring.png" decoding="async" width="120" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Molecular_Borromean_Ring.png/180px-Molecular_Borromean_Ring.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Molecular_Borromean_Ring.png/240px-Molecular_Borromean_Ring.png 2x" data-file-width="288" data-file-height="288" /></a></span></div> <div class="gallerytext"><a href="/wiki/Molecular_Borromean_rings" title="Molecular Borromean rings">Molecular Borromean rings</a></div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mechanically_interlocked_molecular_architectures&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFBrowneFeringa2006" class="citation journal cs1">Browne, Wesley R.; 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(2011-04-26). "Macrocycle Size Matters: "Small" Functionalized Rotaxanes in Excellent Yield Using the CuAAC Active Template Approach". <i><a href="/wiki/Angewandte_Chemie_International_Edition" class="mw-redirect" title="Angewandte Chemie International Edition">Angewandte Chemie International Edition</a></i>. <b>50</b> (18): 4151–4155. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.201100415">10.1002/anie.201100415</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1521-3773">1521-3773</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21462287">21462287</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition&rft.atitle=Macrocycle+Size+Matters%3A+%22Small%22+Functionalized+Rotaxanes+in+Excellent+Yield+Using+the+CuAAC+Active+Template+Approach&rft.volume=50&rft.issue=18&rft.pages=4151-4155&rft.date=2011-04-26&rft.issn=1521-3773&rft_id=info%3Apmid%2F21462287&rft_id=info%3Adoi%2F10.1002%2Fanie.201100415&rft.aulast=Lahlali&rft.aufirst=Hicham&rft.au=Jobe%2C+Kajally&rft.au=Watkinson%2C+Michael&rft.au=Goldup%2C+Stephen+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMechanically+interlocked+molecular+architectures" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFParhamWindischVögtle1999" class="citation journal cs1">Parham, Amir Hossain; Windisch, Björna; Vögtle, Fritz (1999-05-01). <a rel="nofollow" class="external text" href="http://onlinelibrary.wiley.com/doi/10.1002/(SICI)1099-0690(199905)1999:53.0.CO;2-Q/abstract">"Chemical Reactions in the Axle of Rotaxanes – Steric Hindrance by the Wheel"</a>. <i><a href="/wiki/European_Journal_of_Organic_Chemistry" title="European Journal of Organic Chemistry">European Journal of Organic Chemistry</a></i>. <b>1999</b> (5): 1233–1238. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F%28sici%291099-0690%28199905%291999%3A5%3C1233%3A%3Aaid-ejoc1233%3E3.0.co%3B2-q">10.1002/(sici)1099-0690(199905)1999:5<1233::aid-ejoc1233>3.0.co;2-q</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1099-0690">1099-0690</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Organic+Chemistry&rft.atitle=Chemical+Reactions+in+the+Axle+of+Rotaxanes+%E2%80%93+Steric+Hindrance+by+the+Wheel&rft.volume=1999&rft.issue=5&rft.pages=1233-1238&rft.date=1999-05-01&rft_id=info%3Adoi%2F10.1002%2F%28sici%291099-0690%28199905%291999%3A5%3C1233%3A%3Aaid-ejoc1233%3E3.0.co%3B2-q&rft.issn=1099-0690&rft.aulast=Parham&rft.aufirst=Amir+Hossain&rft.au=Windisch%2C+Bj%C3%B6rna&rft.au=V%C3%B6gtle%2C+Fritz&rft_id=http%3A%2F%2Fonlinelibrary.wiley.com%2Fdoi%2F10.1002%2F%28SICI%291099-0690%28199905%291999%3A53.0.CO%3B2-Q%2Fabstract&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMechanically+interlocked+molecular+architectures" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mechanically_interlocked_molecular_architectures&action=edit&section=9" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchill1971" class="citation book cs1">Schill, Gottfried (1971). <a rel="nofollow" class="external text" href="https://www.elsevier.com/books/catenanes-rotaxanes-and-knots/schill/978-0-12-625450-1"><i>Catenanes, Rotaxanes, and Knots</i></a> (1st ed.). Academic Press. p. 204. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781483275666" title="Special:BookSources/9781483275666"><bdi>9781483275666</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Catenanes%2C+Rotaxanes%2C+and+Knots&rft.pages=204&rft.edition=1st&rft.pub=Academic+Press&rft.date=1971&rft.isbn=9781483275666&rft.aulast=Schill&rft.aufirst=Gottfried&rft_id=https%3A%2F%2Fwww.elsevier.com%2Fbooks%2Fcatenanes-rotaxanes-and-knots%2Fschill%2F978-0-12-625450-1&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMechanically+interlocked+molecular+architectures" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFG._A._Breault,_C._A._Hunter_and_P._C._Mayers1999" class="citation journal cs1">G. A. Breault, C. A. Hunter and P. C. Mayers (1999). "Supramolecular topology". <i>Tetrahedron</i>. <b>55</b> (17): 5265–5293. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4020%2899%2900282-3">10.1016/S0040-4020(99)00282-3</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Supramolecular+topology&rft.volume=55&rft.issue=17&rft.pages=5265-5293&rft.date=1999&rft_id=info%3Adoi%2F10.1016%2FS0040-4020%2899%2900282-3&rft.au=G.+A.+Breault%2C+C.+A.+Hunter+and+P.+C.+Mayers&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMechanically+interlocked+molecular+architectures" class="Z3988"></span></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist 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class="navbox-group" style="width:1%"><a href="/wiki/Covalent_bond" title="Covalent bond">Covalent</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electron_deficiency" title="Electron deficiency">Electron deficiency</a> <ul><li><a href="/wiki/Three-center_two-electron_bond" title="Three-center two-electron bond">3c–2e</a></li> <li><a href="/wiki/Four-center_two-electron_bond" title="Four-center two-electron bond">4c–2e</a></li> <li><a href="/wiki/Eight-center_two-electron_bond" class="mw-redirect" title="Eight-center two-electron bond">8c–2e</a></li></ul></li> <li><a href="/wiki/Hypervalent_molecule" title="Hypervalent molecule">Hypervalence</a> <ul><li><a href="/wiki/Three-center_four-electron_bond" title="Three-center four-electron bond">3c–4e</a></li></ul></li> <li><a href="/wiki/Agostic_interaction" title="Agostic interaction">Agostic</a></li> <li><a href="/wiki/Bent_bond" title="Bent bond">Bent</a></li> <li><a href="/wiki/Coordinate_covalent_bond" title="Coordinate covalent bond">Coordinate (dipolar)</a></li> <li><a href="/wiki/Pi_backbonding" title="Pi backbonding">Pi backbond</a></li> <li><a href="/wiki/Metal%E2%80%93ligand_multiple_bond" title="Metal–ligand multiple bond">Metal–ligand multiple bond</a></li> <li><a href="/wiki/Charge-shift_bond" title="Charge-shift bond">Charge-shift</a></li> <li><a href="/wiki/Hapticity" title="Hapticity">Hapticity</a></li> <li><a href="/wiki/Conjugated_system" title="Conjugated system">Conjugation</a></li> <li><a href="/wiki/Hyperconjugation" title="Hyperconjugation">Hyperconjugation</a></li> <li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a> <ul><li><a href="/wiki/Homoaromaticity" title="Homoaromaticity">homo</a></li> <li><a href="/wiki/Bicycloaromaticity" title="Bicycloaromaticity">bicyclo</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a 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srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/300px-Ligatio-covalens.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/400px-Ligatio-covalens.svg.png 2x" data-file-width="597" data-file-height="265" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Chemfm_carbon_monoxide_3_1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/200px-Chemfm_carbon_monoxide_3_1.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/300px-Chemfm_carbon_monoxide_3_1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/400px-Chemfm_carbon_monoxide_3_1.svg.png 2x" data-file-width="99" data-file-height="56" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Pi-Bond.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/200px-Pi-Bond.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/300px-Pi-Bond.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/400px-Pi-Bond.svg.png 2x" data-file-width="1920" data-file-height="1080" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intermolecular_force" title="Intermolecular force">Intermolecular</a><br />(weak)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Van_der_Waals_force" title="Van der Waals force">Van der Waals<br />forces</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/London_dispersion_force" title="London dispersion force">London dispersion</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_bond" title="Hydrogen bond">Hydrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Low-barrier_hydrogen_bond" title="Low-barrier hydrogen bond">Low-barrier</a></li> <li><a href="/wiki/Resonance-assisted_hydrogen_bond" class="mw-redirect" title="Resonance-assisted hydrogen bond">Resonance-assisted</a></li> <li><a href="/wiki/Symmetric_hydrogen_bond" title="Symmetric hydrogen bond">Symmetric</a></li> <li><a href="/wiki/Dihydrogen_bond" title="Dihydrogen bond">Dihydrogen bonds</a></li> <li><a href="/wiki/C%E2%80%93H%C2%B7%C2%B7%C2%B7O_interaction" title="C–H···O interaction">C–H···O interaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-covalent_interactions" class="mw-redirect" title="Non-covalent interactions">Noncovalent</a><br />other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Mechanical</a></li> <li><a href="/wiki/Halogen_bond" title="Halogen bond">Halogen</a></li> <li><a href="/wiki/Chalcogen_bond" title="Chalcogen bond">Chalcogen</a></li> <li><a href="/wiki/Metallophilic_interaction" title="Metallophilic interaction">Metallophilic</a> (<a href="/wiki/Aurophilicity" title="Aurophilicity">aurophilic</a>)</li> <li><a href="/wiki/Intercalation_(chemistry)" title="Intercalation (chemistry)">Intercalation</a></li> <li><a href="/wiki/Stacking_(chemistry)" title="Stacking (chemistry)">Stacking</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction" class="mw-redirect" title="Cation–pi interaction">Cation–pi</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction#Anion–π_interaction" class="mw-redirect" title="Cation–pi interaction">Anion–pi</a></li> <li><a href="/wiki/Salt_bridge_(protein_and_supramolecular)" title="Salt bridge (protein and supramolecular)">Salt bridge</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bond_cleavage" title="Bond cleavage">Bond cleavage</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Heterolysis_(chemistry)" title="Heterolysis (chemistry)">Heterolysis</a></li> <li><a href="/wiki/Homolysis_(chemistry)" title="Homolysis (chemistry)">Homolysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Electron_counting" title="Electron counting">Electron counting</a> rules</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a> <ul><li><a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a></li> <li><a href="/wiki/Baird%27s_rule" title="Baird's rule">Baird's rule</a></li> <li><a href="/wiki/M%C3%B6bius_aromaticity" title="Möbius aromaticity">Möbius</a></li> <li><a href="/wiki/Spherical_aromaticity" title="Spherical aromaticity">spherical</a></li></ul></li> <li><a href="/wiki/Polyhedral_skeletal_electron_pair_theory" title="Polyhedral skeletal electron pair theory">Polyhedral skeletal electron pair theory</a></li> <li><a href="/wiki/Jemmis_mno_rules" title="Jemmis mno rules">Jemmis mno rules</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" 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