Dicyclohepta[ijkl,uvwx]rubicene with Two Pentagons and Two Heptagons as a Stable and Planar Non‐benzenoid Nanographene

Zhang Xi‐Sha; Huang Yan‐Ying; Zhang Jing; Meng Wei; Peng Qian; Kong Ruirui; Xiao Zhenwei; Liu Jie; Huang Miaofei; Yi Yuanping; Chen Liangliang; Fan Qingrui; Lin Gaobo; Liu Zitong; Zhang Guanxin; Jiang Lang; Zhang Deqing

摘要

Abstract > Polycyclic aromatic hydrocarbons with hexagons/pentagons or hexagons/heptagons have been intensively investigated in recent years, but those with simultaneous presence of hexagons, pentagons and heptagons remain rare. In this paper, we report dicyclohepta[ ijkl , uvwx ]rubicene ( DHR ), a non‐benzenoid isomer of dibenzo[ bc , kl ]coronene with two pentagons and two heptagons. We developed an efficient and scalable synthetic method for DHR by using Scholl reaction and dehydrogenation. Crystal structure of DHR shows that the benzenoid rings, two pentagons and two heptagons are coplanar. The bond lengths analysis and the ICSS(1)zz and LOL‐π calculations indicate that the incorporation of two formal azulene moieties has an effect on the conjugated structure. The π‐electrons of benzenoid and pentagon rings are more delocalized. Cyclic voltammetry studies indicate that DHR shows multiple oxidation and reduction potentials. Interestingly, DHR exhibits unusual S <sub>0</sub> to S <sub>2</sub> absorption and abnormal anti‐Kasha S <sub>2</sub> to S <sub>0</sub> emission. Moreover, crystals of DHR exhibit semiconducting behaviour with hole mobility up to 0.082?cm 2 ?V ?1 ?s ?1 . </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> > 近年来，含有六边形/戊酮或六边形/七份的多环芳烃或六边形芳烃，但是那些具有六边形，五葡萄球菌和七术的同时存在的人仍然很少见。在本文中，我们报告了DICYCLOHEPTA [ ijkl </ i> 那 UVWx </ i> ] Rubicene（ dhr </ b> ），Dibenzo的非苯甲酸异构体[ bc </ i> 那 kl </ i> ]核糖烯，有两个五角星和两个骨折。我们开发了一种有效且可扩展的合成方法 dhr </ b> 通过使用Scholl反应和脱氢。晶体结构 dhr </ b> 表明苯突戒指，两张五花参和两种骨都是共面。键合长度分析和ICS（1）ZZ和LOL-π计算表明，两种正式氮烯部分的掺入对共轭结构有影响。苯甲骨和五边形环的π电子更加划分。循环伏安学研究表明 dhr </ b> 显示多种氧化和减少电位。有趣的是， dhr </ b> 展示不寻常的S. <sub> 0 </ sub> 到了 <sub> 2 </ sub> 吸收和异常抗克什S <sub> 2 </ sub> 到了 <sub> 0 </ sub> 排放。而且，晶体的晶体 dhr </ b> 具有孔迁移率的半导体行为，可达0.082Ω厘米 2 </ sup> ？V. ？1 </ sup> ？S. ？1 </ sup> 。 </ 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9期</span><b style="margin: 0 2px;">|</b><span>共5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=Zhang Xi‐Sha&option=202" target="_blank" rel="nofollow">Zhang Xi‐Sha;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Huang Yan‐Ying&option=202" target="_blank" rel="nofollow">Huang Yan‐Ying;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Jing&option=202" target="_blank" rel="nofollow">Zhang Jing;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Meng Wei&option=202" target="_blank" rel="nofollow">Meng Wei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Peng Qian&option=202" target="_blank" rel="nofollow">Peng Qian;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kong Ruirui&option=202" target="_blank" rel="nofollow">Kong Ruirui;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xiao Zhenwei&option=202" target="_blank" rel="nofollow">Xiao Zhenwei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu Jie&option=202" target="_blank" rel="nofollow">Liu Jie;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Huang Miaofei&option=202" target="_blank" rel="nofollow">Huang Miaofei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yi Yuanping&option=202" target="_blank" rel="nofollow">Yi Yuanping;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Liangliang&option=202" target="_blank" rel="nofollow">Chen Liangliang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Fan Qingrui&option=202" target="_blank" rel="nofollow">Fan Qingrui;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lin Gaobo&option=202" target="_blank" rel="nofollow">Lin Gaobo;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu Zitong&option=202" target="_blank" rel="nofollow">Liu Zitong;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Guanxin&option=202" target="_blank" rel="nofollow">Zhang Guanxin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jiang Lang&option=202" target="_blank" rel="nofollow">Jiang Lang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Deqing&option=202" target="_blank" rel="nofollow">Zhang Deqing;</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>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</p> <p>Beijing National Laboratory for Molecular SciencesChinese Academy of SciencesBeijing 100190 China;</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=azulene&option=203" rel="nofollow">azulene;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=dicycloheptarubicene&option=203" rel="nofollow">dicycloheptarubicene;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=nanographene&option=203" rel="nofollow">nanographene;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=organic semiconductor&option=203" rel="nofollow">organic semiconductor;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Scholl reaction&option=203" rel="nofollow">Scholl reaction;</a> </p> <div class="translation"> 机译：氮烯;二环庚酸钠;纳米图谱;有机半导体;Scholl反应; </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 class="active" >外文文献</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704028161354.html">Dicyclohepta[ijkl,uvwx]rubicene with Two Pentagons and Two Heptagons as a Stable and Planar Non‐benzenoid Nanographene</a> <b>[J]</b> . 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