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class="vector-toc-numb">2</span> <span>Mechanical properties</span> </div> </a> <ul id="toc-Mechanical_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Plastic_crystals_versus_liquid_crystals" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Plastic_crystals_versus_liquid_crystals"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Plastic crystals versus liquid crystals</span> </div> </a> <ul id="toc-Plastic_crystals_versus_liquid_crystals-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">4</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>External links</span> </div> </a> <ul id="toc-External_links-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" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button 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<div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><p>A <b>plastic crystal</b> is a <a href="/wiki/Crystal" title="Crystal">crystal</a> composed of weakly interacting molecules that possess some orientational or conformational degree of freedom. The name plastic crystal refers to the mechanical softness of such phases: they resemble waxes and are easily deformed. If the internal degree of freedom is molecular rotation, the name <b>rotor phase</b> or <b>rotatory phase</b> is also used. Typical examples are the <a href="/wiki/Polymorphism_(materials_science)" class="mw-redirect" title="Polymorphism (materials science)">modifications</a> Methane I and Ethane I. </p><p>In addition to the conventional molecular plastic crystals, there are also emerging ionic plastic crystals, particularly organic ionic plastic crystals (OIPCs) and protic organic ionic plastic crystals (POIPCs).<sup id="cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-0" class="reference"><a href="#cite_note-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Imidazolium_methanesulfonate_as_a_high_temperature_proton_conductor_2-0" class="reference"><a href="#cite_note-Imidazolium_methanesulfonate_as_a_high_temperature_proton_conductor-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> POIPCs are solid protic organic salts formed by proton transfer from a Brønsted acid to a Brønsted base and in essence are <a href="/wiki/Protic_ionic_liquid" title="Protic ionic liquid">protic ionic liquids</a> in the molten state, have found to be promising solid-state proton conductors for high temperature <a href="/wiki/Proton-exchange_membrane_fuel_cell" title="Proton-exchange membrane fuel cell">proton-exchange membrane fuel cells</a>.<sup id="cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-1" class="reference"><a href="#cite_note-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Examples include 1,2,4-triazolium perfluorobutanesulfonate<sup id="cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-2" class="reference"><a href="#cite_note-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Imidazolium" class="mw-redirect" title="Imidazolium">imidazolium</a> <a href="/wiki/Methanesulfonate" class="mw-redirect" title="Methanesulfonate">methanesulfonate</a>.<sup id="cite_ref-Imidazolium_methanesulfonate_as_a_high_temperature_proton_conductor_2-1" class="reference"><a href="#cite_note-Imidazolium_methanesulfonate_as_a_high_temperature_proton_conductor-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>If the internal degree of freedom freezes in a disordered way, an <a href="/wiki/Orientational_glass" title="Orientational glass">orientational glass</a> is obtained. The orientational degree of freedom may be an almost free rotation, or it may be a jump diffusion between a restricted number of possible orientations, as was shown for <a href="/wiki/Carbon_tetrabromide" title="Carbon tetrabromide">carbon tetrabromide</a>.<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> </p><p>X- ray <a href="/wiki/Diffraction" title="Diffraction">diffraction</a> patterns of plastic crystals are characterized by strong diffuse intensity in addition to the sharp Bragg peaks.<sup id="cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-3" class="reference"><a href="#cite_note-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> In a powder pattern this intensity appears to resemble an amorphous background as one would expect for a liquid,<sup id="cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-4" class="reference"><a href="#cite_note-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> but for a single crystal the diffuse contribution reveals itself to be highly structured. The Bragg peaks can be used to determine an average structure but due to the large amount of disorder this is not very insightful. It is the structure of the diffuse scattering that reflects the details of the constrained disorder in the system. Recent advances in two-dimensional detection at synchrotron beam lines facilitate the study of such patterns. </p> <meta property="mw:PageProp/toc" /> <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=Plastic_crystal&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Plastic crystals were discovered in 1938 by Belgian chemist <a href="/wiki/Jean_Timmermans" title="Jean Timmermans">Jean Timmermans</a><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> by their anomalously low <a href="/w/index.php?title=Melting_entropy&action=edit&redlink=1" class="new" title="Melting entropy (page does not exist)">melting entropy</a>. He found that organic substances having a melting entropy lower than approximately 17 J·K<sup>−1</sup>·mol<sup>−1</sup> (~2Rg) are having peculiar properties. Timmermans named them <i><span title="French-language text"><i lang="fr">molecular globulare</i></span></i>. Michils showed in 1948 that these organic compounds are easily deformed and accordingly named them <i>plastic crystals</i> (<span title="French-language text"><i lang="fr">cristaux organiques plastiques</i></span>).<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> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanical_properties">Mechanical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Plastic_crystal&action=edit&section=2" title="Edit section: Mechanical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some plastic crystals, like <a href="/wiki/Ammonia_borane" title="Ammonia borane">aminoborane</a>, when subjected to mechanical stress, exhibit behavior similar to ductile metals such as lead, gold, silver, or copper. This is different from typical molecular crystals, which are brittle and fragile. </p><p>For instance, as they approach their melting point, they become highly ductile and malleable. Under pressure, these crystals can flow through a hole. They exhibit bending, twisting, and stretching with characteristic necking under appropriate stress. These crystals can be molded into various shapes, much like copper or silver.<sup id="cite_ref-Metal‐like_Ductility_in_Organic_Plastic_Crystals:_Role_of_Molecular_Shape_and_Dihydrogen_Bonding_Interactions_in_Aminoboranes_6-0" class="reference"><a href="#cite_note-Metal‐like_Ductility_in_Organic_Plastic_Crystals:_Role_of_Molecular_Shape_and_Dihydrogen_Bonding_Interactions_in_Aminoboranes-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Perfluorocyclohexane" title="Perfluorocyclohexane">Perfluorocyclohexane</a> is plastic to such a degree that it will start to flow under its own weight. <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="Plastic_crystals_versus_liquid_crystals">Plastic crystals versus liquid crystals</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Plastic_crystal&action=edit&section=3" title="Edit section: Plastic crystals versus liquid crystals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like <a href="/wiki/Liquid_crystal" title="Liquid crystal">liquid crystals</a>, plastic crystals can be considered a transitional stage between real solids and real liquids and can be considered <i>soft matter</i>. Another common denominator is the simultaneous presence of order and disorder. Both types of phases are usually observed between the true solid and liquid phases on the temperature scale: </p> <dl><dd><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">true crystal → plastic crystal → true liquid</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">true crystal → liquid crystal → true liquid</span></dd></dl> <p>The difference between liquid and plastic crystals is easily observed in <a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a>. Plastic crystals possess strong long range order and therefore show sharp Bragg reflections.<sup id="cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-5" class="reference"><a href="#cite_note-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Liquid crystals show none or very broad Bragg peaks because the order is not long range. The molecules that give rise to liquid crystalline behavior often have a strongly elongated or disc like shape. Plastic crystals consist usually of almost spherical objects. In this respect one could see them as opposites. </p><p>Certain liquid crystals go through plastic crystal phase before melting. In general, liquid crystals are closer to liquids while plastic crystals are closer to true crystals. </p> <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=Plastic_crystal&action=edit&section=4" 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"><ol class="references"> <li id="cite_note-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_1-5"><sup><i><b>f</b></i></sup></a></span> 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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 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Berlin, Heidelberg: Springer. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-58523-4">10.1007/978-3-642-58523-4</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-41566-4" title="Special:BookSources/978-3-540-41566-4"><bdi>978-3-540-41566-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Schmelze%2C+Erstarrung%2C+Grenzfl%C3%A4chen.+Eine+Einf%C3%BChrung+in+die+Physik+und+Technologie+fl%C3%BCssiger+und+fester+Metalle&rft.place=Berlin%2C+Heidelberg&rft.pub=Springer&rft.date=1999&rft_id=info%3Adoi%2F10.1007%2F978-3-642-58523-4&rft.isbn=978-3-540-41566-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3APlastic+crystal" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 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