Stereoselective Syntheses, Structures, and Properties of Extremely Distorted Chiral Nanographenes Embedding Hextuple Helicenes

Roy Myriam; Berezhnaia Veronika; Villa Marco; Vanthuyne Nicolas; Giorgi Michel; Naubron Jean‐Valère; Poyer Salomé; Monnier Valérie; Charles Laurence; Carissan Yannick; Hagebaum‐Reignier Denis; Rodriguez Jean; Gingras Marc; Coquerel Yoann

摘要

Abstract > We report a molecular design and concept using π‐system elongation and steric effects from helicenes surrounding a triphenylene core toward stable chiral polycyclic aromatic hydrocarbons (PAHs) with a maximal π‐distortion to tackle their aromaticity, supramolecular and molecular properties. The selective syntheses, and the structural, conformational and chiroptical properties of two diastereomeric large multi‐helicenes of formula C <sub>90</sub> H <sub>48</sub> having a triphenylene core and embedding three [5]helicene units on their inner edges and three [7]helicene units at their periphery are reported based on diastereoselective and, when applicable, enantiospecific Yamamoto‐type cyclotrimerizations of racemic or enantiopure 9,10‐dibromo[7]helicene. Both molecules have an extremely distorted triphenylene core, and one of them exhibits the largest torsion angle recorded so far for a benzene ring (twist=36.9°). </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> > 我们通过围绕稳定的手性多环芳族烃（PAHs）朝向稳定的手性多环芳烃（PAHs）朝向稳定的手性多环芳烃（PAH）来报告分子设计和概念。选择性合成，以及式C的两种非对映异构大的多螺升的结构，构象和阴压性能 <sub> 90 </ sub> H <sub> 48 </ sub> 根据非对映选择性，在适用的情况下，报告使用三苯基芯并在其内边缘上嵌入三[5]竖林单位，并在其周边嵌入其周边的三[7]甲丙烯单元。 [7] Helicene。两种分子具有极其扭曲的三苯基芯，其中一个具有迄今为止苯环（Twist = 36.9°）记录的最大扭转角度。 </ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第8期</span><b style="margin: 0 2px;">|</b><span>共8页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Roy Myriam&option=202" target="_blank" rel="nofollow">Roy Myriam;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Berezhnaia Veronika&option=202" target="_blank" rel="nofollow">Berezhnaia Veronika;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Villa Marco&option=202" target="_blank" rel="nofollow">Villa Marco;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Vanthuyne Nicolas&option=202" target="_blank" rel="nofollow">Vanthuyne Nicolas;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Giorgi Michel&option=202" target="_blank" rel="nofollow">Giorgi Michel;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Naubron Jean‐Valère&option=202" target="_blank" rel="nofollow">Naubron Jean‐Valère;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Poyer Salomé&option=202" target="_blank" rel="nofollow">Poyer Salomé;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Monnier Valérie&option=202" target="_blank" rel="nofollow">Monnier Valérie;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Charles Laurence&option=202" target="_blank" rel="nofollow">Charles Laurence;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Carissan Yannick&option=202" target="_blank" rel="nofollow">Carissan Yannick;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hagebaum‐Reignier Denis&option=202" target="_blank" rel="nofollow">Hagebaum‐Reignier Denis;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Rodriguez Jean&option=202" target="_blank" rel="nofollow">Rodriguez Jean;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Gingras Marc&option=202" target="_blank" rel="nofollow">Gingras Marc;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Coquerel Yoann&option=202" target="_blank" rel="nofollow">Coquerel Yoann;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> <p>CNRSAix Marseille UnivMarseille France;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1188.html" title="应用化学">应用化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=aromaticity&option=203" rel="nofollow">aromaticity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=helicenes&option=203" rel="nofollow">helicenes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=polycyclic aromatic hydrocarbons&option=203" rel="nofollow">polycyclic aromatic hydrocarbons;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=stereoselectivity&option=203" rel="nofollow">stereoselectivity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=strained molecules&option=203" rel="nofollow">strained molecules;</a> </p> <div class="translation"> 机译：芳香性;直升机;多环芳烃;立体选择性;应变分子; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li 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2008</span><span>,第5期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-1825_thesis/02022290607.html">构象调控的金纳米棒组装体手性光学性质研究</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=韩冰&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 韩冰</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张伟&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,张伟</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=唐智勇&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,唐智勇</a> <span> <a href="/conference-cn-1825/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 国家自然科学基金委员会“可控自组装体系及其功能化”重大研究计划年度会议暨研讨会 </a> <span> <span> . 2015</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020312595443.html">含有缺陷的手性碳纳米管的电子结构和输运性质</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=魏燕&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 魏燕</a> <span> . 2010</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061203634117.html">一种具有手性旋光性质的自支持手性纳米中空锥阵列薄膜及其制备方法</a> <b>[P]</b> . <span> 中国专利： CN108754418B </span> <span> . 2020.02.07</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120111229111.html">一种具有手性旋光性质的自支持手性纳米中空锥阵列薄膜及其制备方法</a> <b>[P]</b> . <span> 中国专利： CN108754418A </span> <span> . 2018-11-06</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130419554330.html">MANUFACTURING METHOD OF CHIRAL A-AMINONITRILE OF VARIOUS STRUCTURES WITH HIGH YIELD AND EXTREMELY HIGH STEREOSELECTIVITY FROM A-AMIDOSULFONE BY USING A CATALYST FOR A STRECKER REACTION</a> <b>[P]</b> . <span> 外国专利：  KR20120127276A </span> <span> . 2012-11-21</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：链烷反应用催化剂从α-氨基砜制得高产率和极高立体选择性的手性α-氨基异戊二烯结构的方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130454399782.html">A kind of form of the stereoselective syntheses Chiral Amine of method</a> <b>[P]</b> . <span> 外国专利：  CZ355697A3 </span> <span> . 1998-06-17</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：方法的一种立体选择性合成手性胺的形式 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130457926797.html">The cylinder beam joint structure null which uses the concrete component embedding the section whose profile property is good and the section whose profile property is good</a> <b>[P]</b> . <span> 外国专利：  JPH0826618B2 </span> <span> . 1996-03-13</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：圆柱梁节点结构零，它使用混凝土构件嵌入剖面特性良好的部分和剖面特性良好的部分 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704028161035','4',7,2,1,'',this,24)" class="delivery" prompt="010401" title="通过人工服务将文献原文发送至邮箱" >获取原文</div> <div class="journalsub-pop-up" style="display: none"> <div 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