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<!DOCTYPE html PUBLIC "-//W3C//DTD XHTML 1.0 Transitional//EN" "http://www.w3.org/TR/xhtml1/DTD/xhtml1-transitional.dtd"> <html xmlns="http://www.w3.org/1999/xhtml"> <head profile="http://gmpg.org/xfn/1"> <title>Computational Organic Chemistry » Planar ring in a nano-Saturn</title> <meta name="google-site-verification" content="g1Myv4tUVAmqRbwZeBi7IPuSZpP64RWjVJ6itIoouCo"> <meta http-equiv="Content-Type" content="text/html; charset=UTF-8"> <style type="text/css" media="screen">@import url( /blog/wp-content/themes/comporg/style.css);</style> <link rel="stylesheet" id="wp-block-library-css" href="/blog/wp-includes/css/dist/block-library/style.min.css?ver=5.6.1" type="text/css" media="all"> <link rel="canonical" href="/blog/archives/4312"> <script type="text/javascript">  </script> </head> <body> <div id="header"> <div id="header_img"></div> </div> <div id="link_section"> <div style="float:left"> <a href="/blog/about">About this Blog</a> | <a href="/">Book Homepage</a> | <a href="http://www.wiley.com/WileyCDA/WileyTitle/productCd-0471713422.html">Purchase the Book</a> </div> </div> <div id="after_links"></div> <div id="content"> <div id="main"> <div class="box"> <h2><a href="/blog/archives/4312" rel="bookmark" title="Permanent Link: Planar ring in a nano-Saturn">Planar ring in a nano-Saturn</a></h2> <div class="post-content"> <p>For the past twelve years, I have avoided posting on any of my own papers, but I will stoop to some shameless promotion to mention my latest paper,<a href="#SaturnBach1"><sup>1</sup></a> since it touches on some themes I have discussed in the past.</p> <p>Back in 2011, Iwamoto, et al. prepared the complex of C<sub>60</sub> <strong>1</strong> surrounded by [10]cycloparaphenylene <strong>2</strong> to make the Saturn-like system <strong>3</strong>.<a href="#SaturnBach2"><sup>2</sup></a> Just last year, Yamamoto, et al prepared the Nano-Saturn <strong>5a</strong> as the complex of <strong>1</strong> with the macrocycle <strong>4a</strong>.<a href="#SaturnBach3"><sup>3</sup></a> The principle idea driving their synthesis was to utilize a ring that is flatter than <strong>2</strong>. The structures of <strong>3</strong> and <strong>5b</strong> (made with the parent macrocycle <strong>4b</strong>) are shown in side view in Figure 1, and clearly seen is the achievement of the flatter ring.</p> <p align="center"><img src="/blog/wp-content/BachrachImg1.png" alt=""></p> <table align="center"> <tbody> <tr align="center"> <td> <img src="/blog/wp-content/10cppC60_side.png"><br><strong>3</strong> </td> </tr> <tr align="center"> <td> <img src="/blog/wp-content/saturnC_side.png"> <br><strong>5b</strong> </td> </tr> <tr align="center"> <td> <img src="/blog/wp-content/saturnN1_side.png"> <br><strong>7</strong> </td> </tr> </tbody> </table> <p></p> <p align="center"><strong>Figure 1</strong>. Computed structures of <strong>3, 5</strong>, and <strong>7</strong>.</p> <p>However, the encompassing ring is not flat, with dihedral angles between the anthrenyl groups of 35掳. This twisting is due to the steric interactions of the <em>ortho-ortho’</em> hydrogens. A few years ago, my undergraduate student David St眉ck and I suggested that selective substitution of a nitrogen for one of the C-H groups would remove the steric interaction,<a href="#SaturnBach4"><sup>4</sup></a> leading to a planar poly-aryl system, such as making twisted biphenyl into the planar 2-(2-pyridyl)-pyridine (Scheme 1)</p> <p></p> <p align="center"><strong>Scheme 1</strong>.</p> <p align="center"><img src="/blog/wp-content/BachrachImg2.png" alt=""></p> <p>Following this idea leads to four symmetrical nitrogen-substituted analogues of <strong>4b</strong>; and I鈥檒l mention just one of them here, <strong>6</strong>. </p> <p align="center"><img src="/blog/wp-content/BachrachImg3.png" alt=""></p> <p>As expected, <strong>6</strong> is perfectly flat. The ring remains flat even when complexed with <strong>1 </strong>(as per B3LYP-D3(BJ)/6-31G(d) computations), see the structure of <strong>7</strong> in Figure 1.</p> <p>I also examined the complex of the flat macrocycle <strong>6</strong> (and its isomers) with a [5,5]-nanotube, <strong>7</strong>. The tube bends over to create better dispersion interaction with the ring, which also become somewhat non-planar to accommodate the tube. Though not mentioned in the paper, I like to refer to <strong>7</strong> as Beyoncene, in tribute to <em><a href="https://www.youtube.com/watch?v=4m1EFMoRFvY">All the Single Ladies</a></em>.</p> <p align="center"><img src="/blog/wp-content/saturnTubeNtype1.png" alt=""></p> <p align="center"><strong>Figure 2</strong>. Computed structure of <strong>7</strong>.</p> <p>My sister is a graphic designer and she made this terrific image for this work:</p> <p align="center"><img src="/blog/wp-content/saturnCover.jpg" alt=""></p> <h3>References</h3> <p>1. Bachrach, S. M., “Planar rings in nano-Saturns and related complexes.” <em>Chem. Commun.</em> <strong>2019</strong>, <em>55</em>, 3650-3653, DOI: <a href="http://dx.doi.org/10.1039/C9CC01234F">10.1039/C9CC01234F</a>.</p> <p>2. Iwamoto, T.; Watanabe, Y.; Sadahiro, T.; Haino, T.; Yamago, S., “Size-Selective Encapsulation of C<sub>60</sub> by [10]Cycloparaphenylene: Formation of the Shortest Fullerene-Peapod.” <em>Angew. Chem. Int. Ed.</em> <strong>2011</strong>, <em>50</em>, 8342-8344, DOI: <a href="http://dx.doi.org/10.1002/anie.201102302">10.1002/anie.201102302</a> </p> <p>3. Yamamoto, Y.; Tsurumaki, E.; Wakamatsu, K.; Toyota, S., “Nano-Saturn: Experimental Evidence of Complex Formation of an Anthracene Cyclic Ring with C60.” <em>Angew. Chem. Int. Ed.</em> <strong>2018 </strong>, <em>57</em>, 8199-8202, DOI: <a href="http://dx.doi.org/10.1002/anie.201804430">10.1002/anie.201804430</a>.</p> <p>4. Bachrach, S. M.; St眉ck, D., “DFT Study of Cycloparaphenylenes and Heteroatom-Substituted Nanohoops.” <em>J. Org. Chem.</em> <strong>2010</strong>, <em>75</em>, 6595-6604, DOI: <a href="http://dx.doi.org/10.1021/jo101371m">10.1021/jo101371m</a> </p> <h3>InChIs</h3> <p><strong>4b</strong>: InChI=1S/C84H48/c1-13-61-25-62-15-3-51-33-75(62)43-73(61)31-49(1)50-2-14-63-26-64-16-4-52(34-76(64)44-74(63)32-50)54-6-18-66-28-68-20-8-56(38-80(68)46-78(66)36-54)58-10-22-70-30-72-24-12-60(42-84(72)48-82(70)40-58)59-11-23-71-29-69-21-9-57(39-81(69)47-83(71)41-59)55-7-19-67-27-65-17-5-53(51)35-77(65)45-79(67)37-55/h1-48H<br>InChIKey=ZYXXLAYETADMDM-UHFFFAOYSA-N</p> <p><strong>6</strong>: InChI=1S/C72H36N12/c1-2-38-14-44-20-45-25-67(73-31-50(45)13-37(1)44)57-9-4-39-15-51-32-74-68(26-46(51)21-61(39)80-57)58-10-5-40-16-52-33-75-69(27-47(52)22-62(40)81-58)59-11-6-41-17-53-34-76-70(28-48(53)23-63(41)82-59)60-12-7-42-18-54-35-77-71(29-49(54)24-64(42)83-60)72-78-36-55-19-43-3-8-56(38)79-65(43)30-66(55)84-72/h1-36H<br>InChIKey=NSSCKPFBHGOOIJ-UHFFFAOYSA-N</p>  </div> <p class="bottom"> <span class="cat"><a href="/blog/archives/category/aromaticity" rel="category tag">Aromaticity</a> &<a href="/blog/archives/category/host-guest" rel="category tag">host-guest</a></span> <span class="user">Steven Bachrach</span> <span class="date">26 Mar 2019</span> <span class="comments">2 Comments</span> </p> </div>  <h3 id="comments">2 Responses to “Planar ring in a nano-Saturn”</h3> <ol class="commentlist"> <li class="box alt" id="comment-472675"> <p class="cmtinfo"><cite>Eugene Kwan</cite> responded on 28 Mar 2019 at 9:40 am <em><a href="#comment-472675" title="">#</a></em> </p> <div class="bottom"> <p>What a cool molecule!</p> </div> </li> <li class="box " id="comment-478553"> <p class="cmtinfo"><cite>Steven Bachrach</cite> responded on 06 Aug 2019 at 10:03 am <em><a href="#comment-478553" title="">#</a></em> </p> <div class="bottom"> <p>This article has been selected by one of the editors (Prof. Jonathan Steed) as an Editor’s Choice – see this <a href="http://blogs.rsc.org/cc/2019/08/06/chemical-communications-editors-choice/" rel="nofollow">blog post</a>. Editor’s Choice articles are made available at now cost for the month they are selected – so if you don’t have subscription access to <i>ChemComm</i> now until Aug. 31, 2019 is your time to get my article!</p> </div> </li> </ol> <p align="center"></p> </div> <div id="sidebar"> <ul> <li class="box"> <h2> Categories </h2> <ul> <li class="cat-item cat-item-25"> <a href="/blog/archives/category/acidity">Acidity</a> (12) </li> <li class="cat-item cat-item-3"> <a href="/blog/archives/category/aromaticity">Aromaticity</a> (91) </li> <li class="cat-item cat-item-53"> <a href="/blog/archives/category/authors">Authors</a> (153) <ul class="children"> <li class="cat-item cat-item-42"> <a href="/blog/archives/category/authors/borden">Borden</a> (12) </li> <li class="cat-item cat-item-12"> <a href="/blog/archives/category/authors/cramer">Cramer</a> (11) </li> <li class="cat-item cat-item-83"> <a href="/blog/archives/category/authors/grimme">Grimme</a> (17) </li> <li class="cat-item cat-item-9"> <a 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2016</a></li> <li><a href="/blog/archives/date/2016/06">June 2016</a></li> <li><a href="/blog/archives/date/2016/05">May 2016</a></li> <li><a href="/blog/archives/date/2016/04">April 2016</a></li> <li><a href="/blog/archives/date/2016/03">March 2016</a></li> <li><a href="/blog/archives/date/2016/02">February 2016</a></li> <li><a href="/blog/archives/date/2016/01">January 2016</a></li> <li><a href="/blog/archives/date/2015/12">December 2015</a></li> <li><a href="/blog/archives/date/2015/11">November 2015</a></li> <li><a href="/blog/archives/date/2015/10">October 2015</a></li> <li><a href="/blog/archives/date/2015/09">September 2015</a></li> <li><a href="/blog/archives/date/2015/08">August 2015</a></li> <li><a href="/blog/archives/date/2015/07">July 2015</a></li> <li><a href="/blog/archives/date/2015/06">June 2015</a></li> <li><a href="/blog/archives/date/2015/05">May 2015</a></li> <li><a href="/blog/archives/date/2015/04">April 2015</a></li> <li><a href="/blog/archives/date/2015/03">March 2015</a></li> <li><a href="/blog/archives/date/2015/02">February 2015</a></li> <li><a href="/blog/archives/date/2015/01">January 2015</a></li> <li><a href="/blog/archives/date/2014/12">December 2014</a></li> <li><a href="/blog/archives/date/2014/11">November 2014</a></li> <li><a href="/blog/archives/date/2014/10">October 2014</a></li> <li><a href="/blog/archives/date/2014/09">September 2014</a></li> <li><a href="/blog/archives/date/2014/08">August 2014</a></li> <li><a href="/blog/archives/date/2014/07">July 2014</a></li> <li><a href="/blog/archives/date/2014/06">June 2014</a></li> <li><a href="/blog/archives/date/2014/05">May 2014</a></li> <li><a href="/blog/archives/date/2014/04">April 2014</a></li> <li><a href="/blog/archives/date/2014/03">March 2014</a></li> <li><a href="/blog/archives/date/2014/02">February 2014</a></li> <li><a href="/blog/archives/date/2014/01">January 2014</a></li> <li><a href="/blog/archives/date/2013/12">December 2013</a></li> <li><a href="/blog/archives/date/2013/11">November 2013</a></li> <li><a href="/blog/archives/date/2013/10">October 2013</a></li> <li><a href="/blog/archives/date/2013/09">September 2013</a></li> <li><a href="/blog/archives/date/2013/08">August 2013</a></li> <li><a href="/blog/archives/date/2013/07">July 2013</a></li> <li><a href="/blog/archives/date/2013/06">June 2013</a></li> <li><a href="/blog/archives/date/2013/05">May 2013</a></li> <li><a href="/blog/archives/date/2013/04">April 2013</a></li> <li><a href="/blog/archives/date/2013/03">March 2013</a></li> <li><a href="/blog/archives/date/2013/02">February 2013</a></li> <li><a href="/blog/archives/date/2013/01">January 2013</a></li> <li><a href="/blog/archives/date/2012/12">December 2012</a></li> <li><a href="/blog/archives/date/2012/11">November 2012</a></li> <li><a href="/blog/archives/date/2012/10">October 2012</a></li> <li><a href="/blog/archives/date/2012/09">September 2012</a></li> <li><a href="/blog/archives/date/2012/08">August 2012</a></li> <li><a href="/blog/archives/date/2012/07">July 2012</a></li> <li><a href="/blog/archives/date/2012/06">June 2012</a></li> <li><a href="/blog/archives/date/2012/05">May 2012</a></li> <li><a href="/blog/archives/date/2012/04">April 2012</a></li> <li><a href="/blog/archives/date/2012/03">March 2012</a></li> <li><a href="/blog/archives/date/2012/02">February 2012</a></li> <li><a href="/blog/archives/date/2012/01">January 2012</a></li> <li><a href="/blog/archives/date/2011/12">December 2011</a></li> <li><a href="/blog/archives/date/2011/11">November 2011</a></li> <li><a href="/blog/archives/date/2011/10">October 2011</a></li> <li><a href="/blog/archives/date/2011/09">September 2011</a></li> <li><a href="/blog/archives/date/2011/08">August 2011</a></li> <li><a href="/blog/archives/date/2011/07">July 2011</a></li> <li><a href="/blog/archives/date/2011/06">June 2011</a></li> <li><a href="/blog/archives/date/2011/05">May 2011</a></li> <li><a href="/blog/archives/date/2011/04">April 2011</a></li> <li><a href="/blog/archives/date/2011/03">March 2011</a></li> <li><a href="/blog/archives/date/2011/02">February 2011</a></li> <li><a href="/blog/archives/date/2011/01">January 2011</a></li> <li><a href="/blog/archives/date/2010/12">December 2010</a></li> <li><a href="/blog/archives/date/2010/11">November 2010</a></li> <li><a href="/blog/archives/date/2010/10">October 2010</a></li> <li><a href="/blog/archives/date/2010/09">September 2010</a></li> <li><a href="/blog/archives/date/2010/08">August 2010</a></li> <li><a href="/blog/archives/date/2010/07">July 2010</a></li> <li><a href="/blog/archives/date/2010/06">June 2010</a></li> <li><a href="/blog/archives/date/2010/05">May 2010</a></li> <li><a href="/blog/archives/date/2010/04">April 2010</a></li> <li><a href="/blog/archives/date/2010/03">March 2010</a></li> <li><a href="/blog/archives/date/2010/02">February 2010</a></li> <li><a href="/blog/archives/date/2010/01">January 2010</a></li> <li><a href="/blog/archives/date/2009/12">December 2009</a></li> <li><a href="/blog/archives/date/2009/11">November 2009</a></li> <li><a href="/blog/archives/date/2009/10">October 2009</a></li> <li><a href="/blog/archives/date/2009/09">September 2009</a></li> <li><a href="/blog/archives/date/2009/08">August 2009</a></li> <li><a href="/blog/archives/date/2009/07">July 2009</a></li> <li><a href="/blog/archives/date/2009/06">June 2009</a></li> <li><a href="/blog/archives/date/2009/05">May 2009</a></li> <li><a href="/blog/archives/date/2009/04">April 2009</a></li> <li><a href="/blog/archives/date/2009/03">March 2009</a></li> <li><a href="/blog/archives/date/2009/02">February 2009</a></li> <li><a href="/blog/archives/date/2009/01">January 2009</a></li> <li><a href="/blog/archives/date/2008/12">December 2008</a></li> <li><a href="/blog/archives/date/2008/11">November 2008</a></li> <li><a href="/blog/archives/date/2008/10">October 2008</a></li> <li><a href="/blog/archives/date/2008/09">September 2008</a></li> <li><a href="/blog/archives/date/2008/08">August 2008</a></li> <li><a href="/blog/archives/date/2008/07">July 2008</a></li> <li><a href="/blog/archives/date/2008/06">June 2008</a></li> <li><a href="/blog/archives/date/2008/05">May 2008</a></li> <li><a href="/blog/archives/date/2008/04">April 2008</a></li> <li><a href="/blog/archives/date/2008/03">March 2008</a></li> <li><a href="/blog/archives/date/2008/02">February 2008</a></li> <li><a href="/blog/archives/date/2008/01">January 2008</a></li> <li><a href="/blog/archives/date/2007/12">December 2007</a></li> <li><a href="/blog/archives/date/2007/11">November 2007</a></li> <li><a href="/blog/archives/date/2007/10">October 2007</a></li> <li><a href="/blog/archives/date/2007/09">September 2007</a></li> <li><a href="/blog/archives/date/2007/08">August 2007</a></li> <li><a href="/blog/archives/date/2007/07">July 2007</a></li> </ul> </li> </ul> <a rel="license" 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